Shoulda Bet More

Shoulda Bet More with Will Hill - Ep. 338 Steve Fezzik

Bill@vsin.com (Steve Fezzik, Will Hill) — Fri, 15 May 2026 14:55:33 +0000

On this episode of the Shoulda Bet More podcast, Will Hill previews both Game 6s in the NBA, then pro sports bettor Steve Fezzik joins to discuss the NFL schedule release, NBA Playoffs, maximizing comps in Vegas, and much more

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN Pro. You can take 17% off an annual subscription when you use the promo code: POD26. Click Here to get started.

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Shoulda Bet More with Will Hill - Ep. 337 Dave Ross

Bill@vsin.com (Dave Ross, Will Hill) — Wed, 13 May 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill looks at the Cavs - Pistons series and gives a best bet for Game 5, and discusses the NBA offseason. Then, Dave Ross of VSiN By The Books joins to discuss the flailing Mets, the MLB landscape, the PGA championship, and more.

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Shoulda Bet More with Will Hill - Ep. 336 Gill Alexander

Bill@vsin.com (Will Hill, Gill Alexander) — Mon, 11 May 2026 13:54:07 +0000

Will Hill is joined by Gill Alexander to break down several major betting storylines across the sports world.

The guys preview key NBA Playoff matchups including Thunder at Lakers and Pistons at Cavaliers, discussing betting angles, matchups, adjustments, and market movement.

They also react to the NBA Draft Lottery and handicap the updated odds and futures markets surrounding the top picks and teams positioned to reshape the league.

Plus, Will and Gill dive into the 2026 MLB World Series odds, discussing value teams, market perception, and early-season futures opportunities. Plus, betting previews of Monday's MLB slate!

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Shoulda Bet More with Will Hill - Ep. 335 Mitch Moss

Bill@vsin.com (Will Hill, Mitch Moss) — Fri, 8 May 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill previews the Friday night NBA games and recaps the Pistons victory over the Cavs. Then, Mitch Moss of Follow The Money joins to discuss the MLB awards markets, NBA + NHL Playoffs, Vrabel's job status, and more.

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Shoulda Bet More with Will Hill - Ep. 334 Sammy P

Bill@vsin.com (Will Hill, Sam Panayotovich) — Wed, 6 May 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill previews Game 2 of Sixers/Knicks and Wolves/Spurs, the AL Cy Young, and the passing of John Sterling. Then, Sammy P of Fox Sports joins to discuss the NBA + NHL Playoffs, MLB long shot bets, and more.

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Shoulda Bet More with Will Hill - Ep. 333 Jonathan Von Tobel

Bill@vsin.com (Will Hill, Jonathan Von Tobel) — Mon, 4 May 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the weekend of action in the NBA, then Jonathan Von Tobel of Money Moves joins to look ahead to Round 2 of the Playoffs, what went wrong for the Celtics, and who may be on upset alert.

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Shoulda Bet More with Will Hill - Ep. 332 Chris Macero

Bill@vsin.com (Will Hill, Chris Macero) — Fri, 1 May 2026 10:00:00 +0000

In this episode of the Shoulda Bet More podcast, Will Hill previews Friday's NBA games. Plus, Chris Macero, Professional Sports Bettor joins to break down the Kentucky Derby, NBA playoffs, NHL playoffs and the struggles of the Red Sox.

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Shoulda Bet More with Will Hill - Ep. 331 Chris Fallica

Bill@vsin.com (Chris Fallica, Will Hill) — Wed, 29 Apr 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps the night in the NBA and looks ahead to Wednesday and Thursday action. Then “the Bear” Chris Fallica of Fox Sports joins to discuss what to look for in the Kentucky Derby Saturday, as well as futures and takeways so far in MLB and the NHL playoffs.

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Shoulda Bet More with Will Hill - Ep. 330 Doug Kezirian

Bill@vsin.com (Will Hill, Doug Kezirian) — Mon, 27 Apr 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps this weekend's NBA Playoff games and looks ahead to Monday's games. Plus, Will shares his takeaways from the NFL Draft. Also, Doug Kezirian from BetRivers joins to discuss the playoffs, the NFL Draft and more.

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Shoulda Bet More with Will Hill - Ep. 329

Bill@vsin.com (Will Hill) — Fri, 24 Apr 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps a wild first round of the NFL draft and analyzes some of the surprising picks, and recaps the night in the NBA playoffs and looks ahead to the games this weekend. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN Pro. You can take 17% off an annual subscription when you use promo code: POD26. Click https://www.vsin.com/subscribe?tpcc=shoulda-bet-more&utm_source=podcast&utm_medium=simplecast&utm_campaign=shoulda_bet_more to get started.

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Shoulda Bet More with Will Hill - Ep. 328 Jeff Parles

Bill@vsin.com (Jeff Parles, Will Hill) — Wed, 22 Apr 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill previews the Wednesday NBA Playoff action and the NFL Draft. Then, Jeff Parles of ESPN Las Vegas joins to discuss the draft, the NBA Playoffs, and the struggling Mets.

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Shoulda Bet More with Will Hill - Ep. 327 Geoff Schwartz

Bill@vsin.com (Will Hill, Geoff Schwartz) — Mon, 20 Apr 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the opening weekend of the NBA Playoffs and gives his thoughts on the Giants / Bengals trade. Plus, Geoff Schwartz of Fox Sports joins to discuss Monday's NBA Playoff games, the NFL Draft and more.

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Shoulda Bet More with Will Hill - Ep. 326 Jonathan Von Tobel

Bill@vsin.com (Will Hill, Jonathan Von Tobel) — Fri, 17 Apr 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill previews the two remaining NBA Play-In games and discussed all six playoff series that are set. Then, Jonathan Von Tobel of Money Moves joins to breakdown Hornets/Magic, Warriors/Suns, and go through the weekend of playoff action.

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Shoulda Bet More with Will Hill - Ep. 325 Kelley Bydlon

Bill@vsin.com (Will Hill, Kelley Bydlon) — Tue, 14 Apr 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast Will Hill gives his best bets on the Play-In games, then Kelley Bydlon of A Numbers Game joins to break down the NBA playoffs/play-in and shares his best bets for every series. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. You can take 17% off an annual subscription when you use promo code: POD26. Click https://www.vsin.com/subscribe?tpcc=shoulda-bet-more&utm_source=podcast&utm_medium=simplecast&utm_campaign=shoulda_bet_more to get started.

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Shoulda Bet More with Will Hill - Ep. 324 Gill Alexander

Bill@vsin.com (Will Hill, Gill Alexander) — Mon, 13 Apr 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps a wild Masters tournament and gives his thoughts on the NBA Play-In Games and the weekend in MLB. Then Gill Alexander of A Numbers Game joins to recap Rory’s win and talk MLB and NBA Playoffs. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. You can take 17% off an annual subscription when you use promo code: POD26. Click https://www.vsin.com/subscribe?tpcc=shoulda-bet-more&utm_source=podcast&utm_medium=simplecast&utm_campaign=shoulda_bet_more to get started.

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Shoulda Bet More with Will Hill - Ep. 323 Dave Ross

Bill@vsin.com (Will Hill, Dave Ross) — Fri, 10 Apr 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps the first round of The Masters and reacts to Joel Embiid news ahead of the last weekend of the NBA regular season, including a bet in the NBA awards market. Then, Dave Ross of VSiN By The Books to discuss The Masters, MLB, and more.

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Shoulda Bet More with Will Hill - Ep. 322 Chris Fallica

Bill@vsin.com (Will Hill, Chris Fallica) — Wed, 8 Apr 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to Michigan defeating UConn and looks at next year's odds. Then, “The Bear” Chris Fallica from FoxSports joins to recap the National Title Game, and look ahead to some bets in the Masters, MLB, and the NFL Draft.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab the Hoops Special for only $29.99 or take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.

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Shoulda Bet More with Will Hill - Ep. 321 Matt Youmans

Bill@vsin.com (Will Hill, Matt Youmans) — Mon, 6 Apr 2026 10:00:00 +0000

On this episode of Shoulda Bet More, Will Hill previews UConn-Michigan and gives a long shot bet for AL MVP. Plus, Matt Youmans from VSIN joins the show to discuss the National Championship Game, the Masters and his thoughts on the MLB season so far.

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Shoulda Bet More with Will Hill - Ep. 320 Steve Fezzik

Bill@vsin.com (Steve Fezzik, Will Hill) — Fri, 3 Apr 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill previews the two Final Four matchups and gives his best bets. Then, pro bettor Steve Fezzik joins to discuss his thoughts on the National semifinals, betting angles, the rise of exchanges, tennis vs Todd Wishnev, and so much more.

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Shoulda Bet More with Will Hill - Ep. 319 Ian Eagle

Bill@vsin.com (Will Hill, Ian Eagle) — Wed, 1 Apr 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill takes a look at Most Outstanding Player odds for March Madness and discusses the Final 4 matchups. Then, Ian Eagle of CBS Sports joins to relive calling the final moments of Duke/UConn, what he expects this weekend, and much more.

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Shoulda Bet More with Will Hill - Ep. 318 Jonathan Von Tobel

Bill@vsin.com (Will Hill, Jonathan Von Tobel) — Mon, 30 Mar 2026 10:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will Hill reacts to a classic UConn - Duke game in the Elite Eight. Plus, Jonathan Von Tobel from Money Moves joins the show to recap UConn-Duke, preview the Final Four and NBA Playoffs.

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Shoulda Bet More with Will Hill - Ep. 317 Jeff Parles

Bill@vsin.com (Jeff Parles, Will Hill) — Thu, 26 Mar 2026 22:49:03 +0000

On this episode of the Shoulda Bet More podcast, Will Hill previews the Sweet 16 games for Friday. Then Jeff Parles of ESPN Las Vegas joins to break down Friday's college basketball games and give his predictions for the MLB season.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN Pro. Grab the Hoops Special for only $29.99 or take 17% off an annual subscription when you use promo code: POD26. Click here to get started.

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Shoulda Bet More with Will Hill - Ep. 317 Mitch Moss

Bill@vsin.com (Will Hill, Mitch Moss) — Wed, 25 Mar 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives his best bets for the Sweet Sixteen, and previews MLB Opening Day. Then, Mitch Moss of Follow the Money joins to share his thoughts on the NCAA Tournament, MLB Bets, and more.

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Shoulda Bet More with Will Hill - Ep. 316 Gill Alexander

Bill@vsin.com (Will Hill, Gill Alexander) — Mon, 23 Mar 2026 15:43:42 +0000

On this episode of the Shoulda Bet More podcast, Will Hill is joined by Gill Alexander of A Numbers Game to recap the weekend in college hoops, look ahead to the sweet 16, and talk about his favorite MLB bets

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Shoulda Bet More with Will Hill - Ep. 315 John Laghezza

Bill@vsin.com (Will Hill, John Laghezza) — Fri, 20 Mar 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast Will Hill recaps the opening day of the NCAA Tournament, and previews the Friday games including some best bets . Then 2025 Fantasy Baseball Writer of the Year John Laghezza joins to preview the upcoming MLB season. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab the Hoops Special for only $29.99 or take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.

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Shoulda Bet More with Will Hill - Ep. 314 Kiev O’Neil

Bill@vsin.com (Will Hill, Kiev O'Neil) — Mon, 16 Mar 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast Will Hill reacts to the bracket reveal, and gives his best bets for Round 1. Then, Kiev O’Neil of the Oddsbreakers joins to discuss his takeaways from the bracket, who he’s bet + much more. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab the Hoops Special for only $29.99 or take 17% off an annual subscription when you use promo code: POD26. Click https://www.vsin.com/subscribe?tpcc=shoulda-bet-more&utm_source=podcast&utm_medium=simplecast&utm_campaign=shoulda_bet_more to get started.

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Shoulda Bet More with Will Hill - Ep. 313 Tim Murray

Bill@vsin.com (Tim Murray, Will Hill) — Fri, 13 Mar 2026 16:06:32 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the day in CBB on Thursday and talks WBC. Then Tim Murray of VSIN Primetime joins to break down Miami Ohio's chances to make the tourney, Friday's Best Bets, and more.

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Shoulda Bet More with Will Hill - Ep. 312 Chris Fallica

Bill@vsin.com (Will Hill, Chris Fallica) — Wed, 11 Mar 2026 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives his thoughts on conference tournament week, including some best bets. Then “The Bear” Chris Fallica of FOX Sports joins to discuss the ACC tournament, long shot tourney bets, WBC, and more.

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Shoulda Bet More with Will Hill - Ep. 311 Jeff Parles

Bill@vsin.com (Will Hill, Jeff Parles) — Mon, 9 Mar 2026 10:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will Hill reacts to this weekend's college basketball games and World Baseball Classic action. Plus, Jeff Parles of ESPN Las Vegas joins to discuss conference tournament futures, his long-shots, and favorite MLB bets.

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Shoulda Bet More with Will Hill - Ep. 310 Jonathan Von Tobel

Bill@vsin.com (Will Hill, Jonathan Von Tobel) — Fri, 6 Mar 2026 11:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will Hill previews tonight's college basketball games. Plus, Jonathan Von Tobel joins to discuss college basketball conference tournaments, the surging Charlotte Hornets, his MLB bets and more.

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Shoulda Bet More with Will Hill - Ep. 309

Bill@vsin.com (Will Hill) — Wed, 4 Mar 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast Will Hill gives his breakdown of the WBC, with best bets, a couple of long shots for MVP, and a pick to win it all. Then Will discusses NFL draft + free agency with a bet for who will go 2nd overall. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab your first month for only $9.99 or take 17% off an annual subscription when you use promo code: POD26. Click https://www.vsin.com/subscribe?tpcc=shoulda-bet-more&utm_source=podcast&utm_medium=simplecast&utm_campaign=shoulda_bet_more to get started.

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Shoulda Bet More with Will Hill - Ep. 308 Kiev O’Neil

Bill@vsin.com (Will Hill, Kiev O'Neil) — Mon, 2 Mar 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the weekend in college hoops and gives a best for conference tournament week. Then Kiev O’Neil of The Oddsbreakers joins to break down conference tournament odds, the bubble , Miami Ohio and more! Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab your first month for only $9.99 or take 17% off an annual subscription when you use promo code: POD26. Click https://www.vsin.com/subscribe?tpcc=shoulda-bet-more&utm_source=podcast&utm_medium=simplecast&utm_campaign=shoulda_bet_more to get started.

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Shoulda Bet More with Will Hill - Ep. 307 Jensen Lewis

Bill@vsin.com (Will Hill, Jensen Lewis) — Fri, 27 Feb 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast Will Hill reacts to UConn embarrassing St John’s Wednesday night, and discusses their shot at a #1 seed. Then, Jensen Lewis of VSIN By the Books joins to break down the WBC, his favorite MLB bets, facing A-Rod, Manny, and Jeter, and more.

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Shoulda Bet More with Will Hill - Ep. 306 Chris Fallica

Bill@vsin.com (Chris Fallica, Will Hill) — Mon, 23 Feb 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the U.S. winning gold in hockey, as well as the weekend in college hoops. Then, “the Bear” Chris Fallica from Fox Sports joins to give his thoughts on the Gold medal game, CBB Futures, MLB early bets, and more.

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Shoulda Bet More with Will Hill - Ep. 305 Adam Burke

Bill@vsin.com (Will Hill, Adam Burke) — Fri, 20 Feb 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to UConn’s recent struggles, gives his thoughts on Duke/Michigan, and an MLB long shot future. Then, Adam Burke, managing editor of VSIN, joins to break down MLB division by division, awards and future bets, lockout thoughts, and more.

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Shoulda Bet More with Will Hill - Ep. 304 Brad Thomas

Bill@vsin.com (Will Hill, Brad Thomas) — Wed, 18 Feb 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives his thoughts on NBA Futures coming out of the All Star Break, and Brad Thomas of PGA Tour joins to discuss his favorite golf outrights, NBA futures, awards, and more.

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Shoulda Bet More with Will Hill - Ep. 303 Todd Wishnev

Bill@vsin.com (Todd Wishnev, Will Hill) — Mon, 16 Feb 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps the weekend in college hoops, and pro bettor Todd Wishnev joins to discuss college basketball futures, how many teams can win it all, playing tennis vs Steve Fezzik, and more.

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Shoulda Bet More with Will Hill - Ep. 302 Ryan Glasspiegel

Bill@vsin.com (Will Hill, Ryan Glasspiegel) — Fri, 13 Feb 2026 11:00:00 +0000

In this episode of the Shoulda Bet More Will Hill gives his thoughts on the NBA All-Star break. Plus, Will gives his MLB futures best bet. Then Ryan Glasspiegel of Front Office Sports joins to give his thoughts on NBA tanking, Kalshi controversies and visiting Las Vegas.

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Shoulda Bet More with Will Hill - Ep. 301 Dave Ross

Bill@vsin.com (Dave Ross, Will Hill) — Wed, 11 Feb 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill looks at the NFL odds for next year, and gives his thoughts on the tanking issue in the NBA. Then, Dave Ross of VSIN By the Books joins to discuss SB odds for next year, MLB bets he’s made, golf, UFC, and more.

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Shoulda Bet More with Will Hill - Ep. 300 Gill Alexander

Bill@vsin.com (Will Hill, Gill Alexander) — Mon, 9 Feb 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Seahawks dominant win over the Patriots. Then, Gill Alexander of A Numbers Game joins to discuss his takeaways from the game, what we can learn from this Seahawks surprise run, and what bets he likes in CBB and MLB now that football is over.

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Shoulda Bet More with Will Hill - Ep. 299 Jeff Parles

Bill@vsin.com (Jeff Parles, Will Hill) — Fri, 6 Feb 2026 11:00:00 +0000

In this episode of Shoulda Bet More, Will Hill gives his final take on Super Bowl LX and adds his best bets. Plus, Jeff Parles of ESPN Las Vegas joins the show to break down the big game and give his best prop bets, MVP long shot, and discuss the college basketball landscape.

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Shoulda Bet More with Will Hill - Ep. 298 Kelley Bydlon

Bill@vsin.com (Kelley Bydlon, Will Hill) — Wed, 4 Feb 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives his thoughts on the NBA trade deadline, and recaps his bets for Pats/Seahawks. Then, Kelley Bydlon of A Numbers Game and Long Shots joins to discuss NBA moves, the Super Bowl, and his golf picks for the week.

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Shoulda Bet More with Will Hill - Ep. 297 Colby Marchio

Bill@vsin.com (Colby Marchio, Will Hill) — Mon, 2 Feb 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast Will Hill reacts to the weekend in college hoop and discusses a couple of SB prop bets. Then, Colby Marchio of yourbettingnews joins to discuss Patriots/Seahawks, Mondays CBB card, a long shot MLB bet + More. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab your first month for only $9.99 or take over $60 off an annual subscription when you use promo code: SUPER. Click https://www.vsin.com/subscribe?tpcc=shoulda-bet-more&utm_source=podcast&utm_medium=simplecast&utm_campaign=shoulda_bet_more to get started.

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Shoulda Bet More with Will Hill - Ep. 296 Kiev O'Neil

Bill@vsin.com (Kiev O'Neil, Will Hill) — Fri, 30 Jan 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill previews Michigan / Michigan State and gives his thoughts on the Giannis trade market. Then, Kiev O’Neil of The Oddsbreakers joins to discuss his favorite SB props, the weekend in college hoops, and more.

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Shoulda Bet More with Will Hill - Ep. 295 Jensen Lewis

Bill@vsin.com (Jensen Lewis, Will Hill) — Wed, 28 Jan 2026 16:35:08 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives a best bet for SB MVP, reacts to the fallout of the AFC Title Game, and gives his thoughts on the recent coaching carousel in the NFL. Then former major leaguer Jensen Lewis joins to preview the MLB season with a best for each division and gives his thoughts on the Super Bowl.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN Pro. Grab your first month for only $9.99 or take over $60 off an annual subscription when you use promo code: SUPER. Click here to get started.

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Shoulda Bet More with Will Hill - Ep. 294 Jonathan Von Tobel

Bill@vsin.com (Will Hill, Jonathan Von Tobel) — Mon, 26 Jan 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the conference title games and gives his early thoughts on the Super Bowl. Then, Jonathan Von Tobel of Money Moves joins to discuss the day in the NFL. Did Sean McVay and Sean Payton screw up? Also Seahawks / Pats Part 2.

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Shoulda Bet More with Will Hill - Ep. 293 John Jastremski

Bill@vsin.com (Will Hill) — Fri, 23 Jan 2026 11:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will Hill gives his final thoughts and best bets on the NFL Conference Championship Games. Plus, Will reacts to the latest MLB moves with the Mets and Yankees. Then, John Jastremski of SNY and the Ringer joins the show to break down the NFL Conference Championship Games and MLB hot stove.

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Shoulda Bet More with Will Hill - Ep. 292 Julian Edlow

Bill@vsin.com (Will Hill, Julian Edlow) — Wed, 21 Jan 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps Indiana winning the national title, and gives his thoughts on the conference championship games. Then, Julian Edlow of DK Network joins to break down Patriots/Broncos, Seahawks/Rams, and some thoughts on college basketball and the NBA.

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Shoulda Bet More with Will Hill - Ep. 291

Bill@vsin.com (Will Hill, Jeff Parles) — Mon, 19 Jan 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast Will Hill recaps an epic Divisional Weekend, and gives his pick for the CFP Title Game. Then Jeff Parles of ESPN Las Vegas joins to react to Rams/ Bears, and all the action this weekend. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab your first month for only $9.99 or take over $60 off an annual subscription when you use promo code: SUPER. Click Here to get started.

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Shoulda Bet More with Will Hill - Ep. 290 Mitch Moss

Bill@vsin.com (Will Hill, Mitch Moss) — Fri, 16 Jan 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill goes through every NFL Playoff game with best bets. Then, Mitch Moss of Follow The Money joins to discuss the weekend of NFL action, the CFP National Title Game, gameday snacks, and more.

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Shoulda Bet More with Will Hill - Ep. 289 Dave Ross

Bill@vsin.com (Will Hill, Dave Ross) — Wed, 14 Jan 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to Mike Tomlin stepping down after an ugly loss to the Texans, and gives a few best bets for the Divisional Round of the NFL Playoffs. Then, Dave Ross of VSIN By The Books joins the pod to discuss all 4 NFL Playoff games coming up, Miami vs Indiana, MLB Bets, and more.

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Shoulda Bet More with Will Hill - Ep. 288 Gill Alexander

Bill@vsin.com (Gill Alexander, Will Hill) — Mon, 12 Jan 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps an epic weekend of football, and Gill Alexander of A Numbers Game joins to react to all the weekend action, look ahead to Texans / Steelers, as well as early thoughts for next week’s games.

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Shoulda Bet More with Will Hill - Ep. 287 Sam Panayotovich

Bill@vsin.com (sam panayotovich, Will Hill) — Fri, 9 Jan 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to Miami defeating Ole Miss, and gives a best bet for all 6 playoff games. Then, Sammy P of Fox Sports joins to discuss Wild Card Weekend, Indiana vs Oregon, Futures, and more.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab your first month for only $9.99 or take over 15% off an annual subscription when you use promo code: POD25. Click Here to get started.

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Shoulda Bet More with Will Hill - Ep. 286 Chris "The Bear" Fallica

Bill@vsin.com (Will Hill, Chris Fallica) — Wed, 7 Jan 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives his thoughts and best bets for the two CFP semifinal games. Then “The Bear” Chris Fallica of Fox Sports joins to preview the big games, predict the title winner, give his best bets for NFL playoffs, as well his thoughts on the Jets and Yankees offseason.

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Shoulda Bet More with Jonathan Von Tobel - Ep. 285

Bill@vsin.com (Jonathan Von Tobel, Will Hill) — Mon, 5 Jan 2026 18:55:03 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps Week 18 of the NFL and gives his initial thoughts on the playoff matchups. Then Jonathan Von Tobel of Money Moves joins to react to a crazy Ravens-Steelers ending, NFL awards finals thoughts, playoff picks, and more.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN Pro. Grab your first month for only $9.99 or take over 15% off an annual subscription when you use promo code: POD25. Click here to get started.

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Shoulda Bet More with Will Hill - Ep. 284

Bill@vsin.com (Will Hill) — Fri, 2 Jan 2026 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps the CFP Quarterfinals, and gives his early thoughts looking ahead to the semifinals. Then he breaks down Week 18 in the NFL and gives 4 best bets for the weekend.

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Shoulda Bet More with Will Hill - Ep. 283 Kiev O'Neil

Bill@vsin.com (Kiev O'Neil, Will Hill) — Wed, 31 Dec 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives his thoughts on NFL MVP and previews the CFP games with a best bet on each. Then, Kiev O’Neil of the oddsbreakers joins to breakdown the CFP matchups, bowl games, and his best NFL bets.

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Shoulda Bet More with Will Hill - Ep. 282 Jeff Parles

Bill@vsin.com (will hill, jeff parles) — Mon, 29 Dec 2025 14:33:58 +0000

On this episode of the Shoulda Bet More podcast Will Hill recaps a wild week 17, and looks ahead to week 18. Then Jeff Parles of ESPN Las Vegas joins to discuss a classic Sunday night game, the playoff picture, best bets and more. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab your first month for only $9.99 or take over 15% off an annual subscription when you use promo code: POD25. Click Here to get started. vsin.com/subscribe?tpcc=shoulda-bet-more

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Shoulda Bet More with Will Hill - Ep. 281

Bill@vsin.com (Will Hill) — Fri, 26 Dec 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to Thursday's NFL games, shares his thoughts on the Netflix broadcast, and gives his best bets for College Football Bowl Games and NFL Week 17.

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Shoulda Bet More with Will Hill - Ep. 280 Jensen Lewis

Bill@vsin.com (Jensen Lewis, Will Hill) — Wed, 24 Dec 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast Will Hill breaks down the NFL Xmas games, and Jensen Lewis of Vsin By The Books joins to preview the upcoming NFL weekend, give his thoughts on the CFP, and discuss the MLB offseason.

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Shoulda Bet More with Will Hill - Ep. 279 Geoff Schwartz

Bill@vsin.com (Geoff Schwartz, Will Hill) — Mon, 22 Dec 2025 11:00:00 +0000

In this episode of the Shoulda Bet More podcast Will Hill recaps the weekend in NFL and College Football and gives his best bet for 49ers/Colts. Then Geoff Schwartz of Fox Sports joins to discuss the NFL Playoff picture, the CFP Quarterfinal matchups, holiday cooking tips and more.

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Shoulda Bet More with Will Hill - Ep. 278 Brad Powers

Bill@vsin.com (Will Hill, Brad Powers) — Fri, 19 Dec 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps an instant classic on Thursday Night Football, and gives his best bets for the weekend. Then, pro bettor Brad Powers joins to handicap all four College Football Playoff matchups, bowl games, and gives his pick for who wins it all!

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Shoulda Bet More with Will Hill - Ep. 277 Dave Ross

Bill@vsin.com (Will Hill, Dave Ross) — Wed, 17 Dec 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill previews a huge Rams-Seahawks game and looks at the AFC North race after the Steelers Monday night win. Then, Dave Ross of VSIN By the Books joins to discuss Thursday Night Football, the NFL Playoff Picture, College Football Playoff, as well as the Mets quiet offseason.

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Shoulda Bet More with Will Hill - Ep. 276 Gill Alexander

Bill@vsin.com (Gill Alexander, Will Hill) — Mon, 15 Dec 2025 11:00:00 +0000

On this episode of the Shoulda Bet More Podcast Will Hill reacts to an exciting day in the NFL, and previews MNF. Then Gill Alexander of A Numbers Game joins to discuss the playoff picture, awards, takeaways from Sunday and more.

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Shoulda Bet More with Will Hill - Ep. 275 Jeff Parles

Bill@vsin.com (Will Hill, Jeff Parles) — Fri, 12 Dec 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to a crazy Thursday Night Football game in the NFL, and gives his best bets for the weekend. Then, Jeff Parles of ESPN Las Vegas joins to share his thoughts on the big games of the weekend in the NFL, who takes the Michigan job, the Mets off-season, and more.

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Shoulda Bet More with Will Hill - Ep. 274 Tim Murray

Bill@vsin.com (Tim Murray, Will Hill) — Wed, 10 Dec 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to MNF and previews TNF with a best bet. Then, Tim Murray of VSIN PrimeTime joins to discuss Notre Dame getting left out of the CFP, best bets for the playoff and bowl games, Army/Navy, and more.

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Shoulda Bet More with Will Hill - Ep. 273 Chris Fallica

Bill@vsin.com (Chris Fallica, Will Hill) — Mon, 8 Dec 2025 16:27:40 +0000

In this episode of the Shoulda Bet More Podcast, Will reacts to the College Football Playoff field being revealed and the day in the NFL. Then Chris Fallica from Fox Sports joins to discuss how the committee did, who he likes in Round 1, Bowl games he likes, and more

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Shoulda Bet More with Will Hill - Ep. 272 Jonathan Von Tobel

Bill@vsin.com (Jonathan Von Tobel, Will Hill) — Fri, 5 Dec 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives his best bets for the weekend. Jonathan Von Tobel joins to discuss the Lions and Cowboys, his picks in CFB and the NFL, where Giannis ends up, and more.

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Shoulda Bet More with Will Hill - Ep. 271 Mike Sando

Bill@vsin.com (Mike Sando, Will Hill) — Wed, 3 Dec 2025 11:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will Hill gives his bets for Cowboys/Lions, and reacts to the last college football ranking before the playoff selection on Sunday. Then, Mike Sando of The Athletic joins to discuss his process as an awards voter; are the Pats and Bears for real, the AFC, grilling tips, and more.

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Shoulda Bet More with Will Hill - Ep. 270 Jeff Parles

Bill@vsin.com (Jeff Parles, Will Hill) — Mon, 1 Dec 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps and reacts to a wild weekend in the NFL, and gives his thoughts on MNF and the Lane Kiffin departure. Then, Jeff Parles of ESPN Las Vegas joins to discuss the NFL playoff picture, who’s in and who’s out in CFB, and shares some bets bets.

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Shoulda Bet More with Will Hill - Ep. 269 Brad Powers

Bill@vsin.com (Will Hill, Brad Powers) — Fri, 28 Nov 2025 11:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will Hill reacts to a great day of Thanksgiving NFL action and gives his best bets for the weekend. Then, professional bettor Brad Powers joins the show to discuss his Week 14 college football picks and the playoff picture.

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Shoulda Bet More with Will Hill - Ep. 268 Brad Thomas

Bill@vsin.com (Will Hill, Brad Thomas) — Wed, 26 Nov 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives his bets bets for the Thanksgiving Day games in the NFL, and Brad Thomas of BetUS joins to discuss Thursday’s games, his thoughts on the College Football Playoffs, and picks for some of the marquee games.

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Shoulda Bet More with Will Hill - Ep. 267 Kiev O’Neil

Bill@vsin.com (Kiev O’Neil, Will Hill) — Mon, 24 Nov 2025 11:00:00 +0000

On this episode of the Shoulda Bet More Podcast Will Hill reacts to another exciting day in the NFL. What to make of the Eagles, and did the Chiefs save their season? Then Kiev O’Neil of the oddsbreakers joins to discuss his takeaways from the day , MNF, and + best bets for MNF

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Shoulda Bet More with Will Hill - Ep. 266 Kelley Bydlon

Bill@vsin.com (Will Hill, Kelley Bydlon) — Fri, 21 Nov 2025 11:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will Hill gives his college and NFL picks for the weekend. Then, Kelley Bydlon of A Numbers Game joins to give his best bets in the NFL, discuss the awards markets, and share his thoughts on the NBA so far.

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Shoulda Bet More with Will Hill - Ep. 265 Jeff Parles

Bill@vsin.com (Jeff Parles, Will Hill) — Wed, 19 Nov 2025 11:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will Hill gives a few best bets for College Football this weekend, as well as a long shot NBA Future. Then, Jeff Parles of ESPN Las Vegas joins to discuss the College Football Playoff picture, best bets, the NFL playoffs, and if OKC can break the Warriors regular season wins record.

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Shoulda Bet More with Will Hill - Ep. 264 Geoff Schwartz

Bill@vsin.com (Geoff Schwartz, Will Hill) — Mon, 17 Nov 2025 11:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will reacts to the day in the NFL, and gives a couple of Best Bets. Then former NFL offensive lineman Geoff Schwartz joins to discuss if the Chiefs will actually miss the playoffs, who is the team to beat in the AFC, the college football playoff picture and more.

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Shoulda Bet More with Will Hill - Ep. 263 Jonathan Von Tobel

Bill@vsin.com (Will Hill, Jonathan Von Tobel) — Fri, 14 Nov 2025 11:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will Hill gives his NFL and College Picks for the weekend. Then, Jonathan Von Tobel of VSIN joins to break down the weekend in the NFL, give his bets, discuss the MVP race, and can OKC actually break the record?

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Shoulda Bet More with Will Hill - Ep. 262 Chris "The Bear" Fallica

Bill@vsin.com (Chris "The Bear" Fallica, Will Hill) — Wed, 12 Nov 2025 11:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will Hill gives a best bet for Jets/Patriots and shares a couple of College Football plays. Then, Chris Fallica of Fox Sports joins to discuss the College Football Playoffs Picture, best bets for the week, and more.

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Shoulda Bet More with Will Hill - Ep. 261 Gill Alexander

Bill@vsin.com (Gill Alexander, Will Hill) — Mon, 10 Nov 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast , Will Hill reacts to the day in the NFL, and previews next week. Then Gill Alexander of A Numbers Game joins to discuss the games of the day, takeaways, and preview Packers Eagles.

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Shoulda Bet More with Will Hill - Ep. 260 Mitch Moss

Bill@vsin.com (Will Hill, Mitch Moss) — Fri, 7 Nov 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives his NFL and college best bets for the weekend, as well as a college basketball future. Then, Mitch Moss of Follow The Money joins to discuss all things awards and futures across NFL and CFB.

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Shoulda Bet More with Will Hill - Ep. 259 Tim Murray

Bill@vsin.com (Will Hill, Tim Murray) — Wed, 5 Nov 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives a few best bets for CFB and Raiders / Broncos, and reacts the Jets trades. Then, Tim Murray of VSIN joins to give his thoughts on the College Football Playoffs outlook, best bets for the weekend, and Heisman race.

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Shoulda Bet More with Will Hill - Ep. 258 Dave Ross

Bill@vsin.com (Dave Ross, Will Hill) — Mon, 3 Nov 2025 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to an exciting day in the NFL and gives his takeaways from Sunday. Then, Dave Ross, VSIN Host joins the show to discuss a heartbreaking loss on his Blue Jays World Series bet. Plus, the guys recap Game 7 of the World Series and give out their bets bets for Monday Night Football.

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Shoulda Bet More with Will Hill - Ep. 257 Jensen Lewis

Bill@vsin.com (Jensen Lewis, Will Hill) — Fri, 31 Oct 2025 10:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will Hill previews Game 6 of the World Series, and gives his bets in football for the weekend. Then, former Major League pitcher Jensen Lewis joins to break down the World Series and more.

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Shoulda Bet More with Will Hill - Ep. 256 Jeff Parles

Bill@vsin.com (Will Hill, Jeff Parles) — Wed, 29 Oct 2025 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Blue Jays tying the World Series once again, and gives his best bets for Game 5 and TNF. Then, Jeff Parles of ESPN Las Vegas joins the pod to discuss the World Series - can someone on LA, other than Ohtani, win the MVP? Also, they talk about the NFL and College Football weekend ahead.

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Shoulda Bet More with Will Hill - Ep. 255

Bill@vsin.com (Will Hill) — Mon, 27 Oct 2025 10:00:00 +0000

On this episode of the shoulda bet more podcast, Will Hill reacts to the day in the NFL- Are the Ravens Back? And Jets get their first win in dramatic fashion. Then Will gives his best bet for MNF and a couple bets for Game 3 of the World Series.

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Shoulda Bet More with Will Hill - Ep. 254 Tommy Lorenzo

Bill@vsin.com (Will Hill, Tommy Lorenzo) — Fri, 24 Oct 2025 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives his best bets for the weekend, previews the World Series, and reacts to the Terry Rozier and Chauncey Billups arrests and what it means for the betting world going forward. Then, Tommy Lorenzo of the Cover the Weekend Podcast joins to break down Dodgers / Jays, give an MVP Sleeper for the series, talk college football, and more.

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Shoulda Bet More with Will Hill - Ep. 253 Chris "The Bear" Fallica

Bill@vsin.com (Will Hill, Chris Fallica) — Wed, 22 Oct 2025 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps a dramatic Game 7 of the ALCS, looks ahead to the World Series, and gives a few NBA Best Bets. Then, Chris “The Bear” Fallica of Fox Sports joins the podcast to discuss Dodgers / Blue Jays, College Football Playoff overview, how he would fix the Jets, and more.

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Shoulda Bet More with Will Hill - Ep. 252 Kiev O'neil

Bill@vsin.com (Kiev O'neil, Will Hill) — Mon, 20 Oct 2025 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill talks about NFL week seven and is joined by Kiev O'neil to further the chaotic day in the NFL.

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Shoulda Bet More with Will Hill - Ep. 251 Jonathan Von Tobel

Bill@vsin.com (Will Hill, Jonathan Von Tobel) — Fri, 17 Oct 2025 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives his college and NFL picks for the weekend, and discusses the MLB games for Friday. Then, Jonathan Von Tobel joins and gives his best bets, futures, and more.

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Shoulda Bet More with Will Hill - Ep. 250 Iain MacMillan

Bill@vsin.com (Will Hill, Iain MacMillan) — Wed, 15 Oct 2025 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will previews Thursday Night Football, and gives his reaction to Monday Night Football - Are the Bills in Trouble? Are the Falcons for real? Then Iain MacMillan of Sports Illustrated joins to discuss his bets for the weekend, the ALCS, and more.

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Shoulda Bet More with Will Hill - Ep. 249 Geoff Schwartz

Bill@vsin.com (Geoff Schwartz, Will Hill) — Mon, 13 Oct 2025 10:00:00 +0000

On this episode of the shoulda bet more podcast , Will Hill reacts to the chiefs beating the lions and all the Sunday action in the NFL, and looks ahead to the 2 Monday night football games and shares his bets for the MLB playoffs . Then , Geoff Schwartz of Fox sports joins to discuss Bills /Falcons and Bears/Commanders , give his take on James Franklin being fired and More

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Shoulda Bet More with Will Hill - Ep. 248 Matt Youmans

Bill@vsin.com (Will Hill, Matt Youmans) — Fri, 10 Oct 2025 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill gives his NFL and college football picks, along with a play for Game 5 of the ALDS between the Tigers and Mariners. Will also reacts to seeing the Yankees get eliminated in person. Plus, Matt Youmans joins to discuss the outlook for the Yankees going forward, the latest with UNC football, and his football bets.

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Shoulda Bet More with Will Hill - Ep. 247

Bill@vsin.com (Will Hill) — Wed, 8 Oct 2025 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill recaps a wild comeback by the Yankees, previews the four MLB games on Wednesday, then dives into College Football and the games he likes for this weekend and gives some big picture thoughts on the playoff picture.

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Shoulda Bet More with Will Hill - Ep. 246 Gill Alexander

Bill@vsin.com (Gill Alexander, Will Hill) — Mon, 6 Oct 2025 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Yankees brutal weekend up north, looks ahead to Game 3, and recaps the day in the NFL. Then, Gill Alexander of A Numbers Game joins to try to make sense of the Arizona Cardinals collapse, discuss if the Ravens are done, and give his thoughts on Monday's MLB and NFL games.

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Shoulda Bet More with Will Hill - Ep. 245 Ben Wilson

Bill@vsin.com (Ben WIlson, Will Hill) — Fri, 3 Oct 2025 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Will reacts to the Yankees beating the Red Sox, looks ahead to the ALDS and NLDS, and Ben Wilson joins to discuss the MLB playoffs, 49ers/Rams, and his NFL picks for the weekend.

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Shoulda Bet More with Will Hill - Ep. 244 Jeff Parles

Bill@vsin.com (Jeff Parles, Will Hill) — Wed, 1 Oct 2025 10:00:00 +0000

On this episode of the shoulda bet more podcast will hill recaps a brutal Yankees loss to the Red Sox, previews game 2 , and gives his best bets for Tuesday . Then, Jeff Parles from sports by the book joins to discuss the day in MLB, Wednesdays games, NFL takeaways 4 weeks in and more

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Shoulda Bet More with Will Hill - Ep. 243 Nic Larson

Bill@vsin.com (Nic Larson, Will Hill) — Mon, 29 Sep 2025 10:00:00 +0000

On this episode of the Shoulda Bet more Podcast, Will Hill reacts to Sunday's NFL action and discusses the Chiefs win over the Ravens. Plus, MLB handicapper Nic Larson joins the show to discuss the MLB playoffs and give his best bets.

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Shoulda Bet More with Will Hill - Ep. 242 Brad Powers

Bill@vsin.com (Brad Powers, Will Hill) — Fri, 26 Sep 2025 10:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will Hill gives his college football and NFL picks for the weekend. Then Pro Bettor Brad Powers joins to discuss all the big college games this weekend, his best bets, and his thoughts on the Heisman and National title picture.

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Shoulda Bet More with Will Hill - Ep. 241 Dave Ross

Bill@vsin.com (Dave Ross, Will Hill) — Wed, 24 Sep 2025 10:00:00 +0000

On this episode of the Shoulda Bet More podcast , Will Hill recaps a wild Tuesday night in MLB, gives a handful of Best Bets for Wednesday, then Dave Ross of VSiN By The Books joins to discuss the Mets crazy comeback, who gets the final NL Wild card spot , futures odds, and more.

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Shoulda Bet More with Will Hill - Ep. 240 Jensen Lewis

Bill@vsin.com (Jensen Lewis, Will Hill) — Mon, 22 Sep 2025 10:00:00 +0000

On this episode of Shoulda Bet More, Will Hill recaps a wild day in the NFL, previews Monday Night Football, and breaks down the MLB playoff picture as we enter the final week of the season. Plus, Jensen Lewis from VSiN By The Books joins the show to discuss MNF, recap today's NFL action and which teams will make the MLB Playoffs.

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Shoulda Bet More with Will Hill - Ep. 239 Adam Kaufman

Bill@vsin.com (Adam Kaufman, Will Hill) — Fri, 19 Sep 2025 10:00:00 +0000

On this episode of Shoulda Bet More, Will Hill takes a look at the Sunday NFL Week 3 slate and gives out his best bets. Then, Adam Kaufman of Your Betting News joins to give out his NFL Week 3 picks, plus talk about the Red Sox making the postseason this year.

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Shoulda Bet More with Will Hill - Ep. 238 Sammy P

Bill@vsin.com (Sammy P, Will Hill) — Wed, 17 Sep 2025 10:00:00 +0000

On this episode of the shoulda bet more podcast Will Hill takes a look at the MLB playoff picture and World Series odds and gives out a best bet for TNF. Then, Sammy P of Fox sports joins to discuss lack of NFL Upsets , this weeks games , futures + More

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Shoulda Bet More with Will Hill - Ep. 237 - Stormy Buonantony

Bill@vsin.com (Will Hill, Stormy Buonantony) — Mon, 15 Sep 2025 10:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will Hill reacts to the Week 2 of the NFL, discusses the possibility of the Chiefs missing the playoffs and previews Monday Night Football. Then, Stormy Buonantony from ESPN and VSiN joins to discuss the NFL, her Monday Night Football picks, thoughts on college football, the best restaurants in college towns and more.

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Shoulda Bet More with Will Hill - Ep. 236 - Jonathan Von Tobel

Bill@vsin.com (Will Hill, Jonathan Von Tobel) — Fri, 12 Sep 2025 10:00:00 +0000

On this episode of Shoulda Bet More, Will gives out his college and NFL picks for the weekend. Then, Jonathan Von Tobel of VSiN joins to discuss his favorite NFL bets, teams he’s changed his mind on after a week, and some best bets in college football. JVT also shares his thoughts on the MLB playoff picture.

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Shoulda Bet More with Will Hill - Ep. 235 - Chris “The Bear” Fallica

Bill@vsin.com (Will Hill, Chris Fallica) — Wed, 10 Sep 2025 10:00:00 +0000

On this episode of the Shoulda Bet More Podcast, Will reacts to a wild Monday Night Football game, previews TNF, and gives his best bets as well as an awards bet in the NFL. Then, Chris “ The Bear” Fallica from Fox Sports joins to discuss his bets for college football this weekend, a team he still thinks has value in the futures market, the MLB playoff picture, and college towns with the best restaurants.

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Shoulda Bet More with Will Hill - Ep. 234 - Geoff Schwartz

Bill@vsin.com (Geoff Schwartz, Will Hill) — Mon, 8 Sep 2025 10:00:00 +0000

On this episode, Will Hill reacts to week 1, and then former NFL offensive lineman Geoff Schwartz of Fox Sports joins the pod to discuss his takeaways from the weekend. The guys preview Monday Night Football, discuss who is the best team in college football, what Geoff eats when he watches football, and more.

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Shoulda Bet More with Will Hill - Ep. 233 - Mitch Moss

Bill@vsin.com (Mitch Moss, Will Hill) — Fri, 5 Sep 2025 10:00:00 +0000

On this episode, Will Hill gives his college + NFL Picks for the weekend, including a long shot NFL bet. Then, Mitch Moss from Follow the Money joins and goes over all of his futures /awards bets in the NFL, his NFL+ College Picks, his thoughts on Belichick and UNC, and more

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Shoulda Bet More with Will Hill - Ep. 232 - John Jastremski

Bill@vsin.com (Will Hill, John Jastremski) — Wed, 3 Sep 2025 10:50:10 +0000

On this episode, Will Hill gives his thoughts on UNC losing to TCU and gives out his pick for the Cowboys /Eagles. Then, John Jastremski of The Ringer joins and discusses Thursday Night football, his best bets for NFL Week 1, survivor, and the MLB Playoff Picture.

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Shoulda Bet More with Will Hill - Ep. 231 - Gill Alexander

Bill@vsin.com (Will Hill, Gill Alexander) — Mon, 1 Sep 2025 14:26:09 +0000

Will Hill reacts to Week 1 of the College Football season, gives his thoughts and a pick for TCU /UNC, breaks down the MLB Pennant Races, then Gill Alexander of A Numbers Game joins to discuss the game Monday night, the US Open, NFL, and More

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Shoulda Bet More with Will Hill - Ep. 230 - Kiev O'Neil

Bill@vsin.com (Kiev O'Neil, Will Hill) — Fri, 29 Aug 2025 18:15:18 +0000

Will Hill gives his thoughts on Week 1 of the college football season and has a few plays on the biggest games. Also, Kiev O’Neil from the oddsbreakers joins to break down the college slate, share his thoughts on futures, and discuss what foods go best with football.

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Shoulda Bet More with Will Hill - Ep. 229 - "The Bear" Chris Fallica

Bill@vsin.com (GoldBoys.com) — Wed, 2 Jul 2025 10:00:00 +0000

As we begin July, we've brought back from Fox Sports, "The Bear" Chris Fallica (@chrisfallica) to discuss what's going to be worth betting in the days to come. We talk some MLB to get an idea of where teams and divisions are at the halfway point of the season. Which teams are worth taking at over/under their projected win totals? Will we see any surprise teams in the 2nd half of the season? Which teams are worth taking the market for July wins? We discuss Chris's approach to College Football betting. How he analyzes teams, how he determines which teams he wants to bet on, and which players he's looking at for the Heisman before the season begins. Plus, Chris gives us his favorite bets for the upcoming Women's Euro so you can get ahead of the books and win some money.

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Shoulda Bet More with Will Hill - Ep. 228 - Gill Alexander

Bill@vsin.com (GoldBoys.com) — Mon, 30 Jun 2025 10:00:00 +0000

To start your week right, we bring back Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod!" We recap this past weekend in baseball to catch you up on what you may have missed. We discuss how the Rafael Devers trade has worked out so far for Gill's Giants. We talk big picture as we approach the halfway point of the season, which team is the best in baseball? Which teams can make a run? Is there any chance that Cal Raleigh takes the AL MVP award from Aaron Judge? Gill also gives us tips on his day to day process for betting in baseball so you can get a leg up on the books. We also discuss Wimbeldon which begins this week. We go through the Men's and Women's bracket and give you our picks and insight for the tournament!

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Shoulda Bet More with Will Hill - Ep. 227

Bill@vsin.com (GoldBoys.com) — Fri, 27 Jun 2025 10:00:00 +0000

On today's episode, we recap the NBA Draft. What surprised Will and what he thought of the picks. Also ESPN's coverage of the draft was not good, is there anything that can be done about it? Will also discusses the state of the MLB as we near the midway point of the season. The Yankees have been ceding ground in the AL East. Could they end up losing the division? Do we have a competition for the AL MVP between Cal Raleigh and Aaron Judge? Are there any teams out of the playoff picture right now that could surprise at the end of the regular season?

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Shoulda Bet More with Will Hill - Ep. 226 - Drew Dinsick

Bill@vsin.com (GoldBoys.com) — Wed, 25 Jun 2025 10:00:00 +0000

Now that the NBA season is over, we turn our attention to the NBA Draft which already happens tonight! To give a betting preview, we've invited Drew Dinsick (@whale_capper) of NBC Sports back to the pod! We preview the draft beyond just the first couple of picks to get an idea of where draftees will end up so you can know whether to be their over/unders. We also catch up on the trades over the first 2 days of the offseason as we look beyond the draft and towards next season's futures. Who do we like to get out of a wide open East and who do we think is worth a bet to win it all? We discuss that and all the off-season's storylines on today's episode!

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Shoulda Bet More with Will Hill - Ep. 225 - Chris Macero

Bill@vsin.com (GoldBoys.com) — Mon, 23 Jun 2025 10:00:00 +0000

The Oklahoma City Thunder are the NBA Champions after winning in what was an anti-climatic game. To talk about it and more we've brought back professional sports bettor and VSiN contributor, Chris Macero (@RealGadge)! We go over game 7 and talk about Haliburton's injury early in the game and how it shaped the rest of the game. We discuss if the NBA season being too long is what leads to injuries like Haliburton's and if the regular season needs to be shortened. We look towards next season by talking about Kevin Durant's trade to the Rockets and which team will rise out of a wide open Eastern Conference. We also talk about futures and awards bets in baseball as we near the halfway point of the season. Finally, Chris lets us in on his preseason betting process for College Football to give you pointers on how to bet this upcoming season.

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Shoulda Bet More with Will Hill - Ep. 224 - Jonathan Von Tobel

Bill@vsin.com (GoldBoys.com) — Fri, 20 Jun 2025 10:00:00 +0000

It all comes down to one game, Sunday night we will have game 7 between the Pacers and the Thunder. We invite back Jonathan Von Tobel (@meJVT) of VSiN Primetime to discuss how we've ended up here and what we believe will happen in game 7. We recap what we just saw in what was a fairly easy win by the Pacers and what effect does it have on how game 7 will play out. We look at the betting lines for game 7 and discuss if we may see a very tight defensive game that will affect the game total. We look at the MVP market to see if any longshots are worth a bet. Also, with the draft coming up just days after game 7, we look to see the betting markets there and give you our favorite bets. We also try to predict how the offseason will go and how different the league will look next year.

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Shoulda Bet More with Will Hill - Ep. 223 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Wed, 18 Jun 2025 10:00:00 +0000

Today, we bring back our favorite guest, Jeff Parles (@jeffparles) of "Sports By The Book!" We recap the Stanley Cup Finals as the Florida Panthers become back to back champions. We also recap Game 5 of the NBA Finals. As the Thunder look to win one more to capture the championship, can the Pacers overcome a potential injury to Haliburton? If the Thunder win it all, where do they rank on some of the all-time teams? We talk a little offseason as we try to figure out where Durant and Giannis end up next season, and who will be the next Head Coach for the Knicks? We discuss the baseball season up to this point as well. What are the playoff implications of the Rafael Devers trade? Are the Giants now legit title contenders? What has happened to the New York Yankees as they can't seem to buy a run. We finish off baseball talk with futures and awards markets. Finally will Aaron Rodgers help or hurt the Pittsburgh Steelers this upcoming season?

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Shoulda Bet More with Will Hill - Ep. 222

Bill@vsin.com (GoldBoys.com) — Mon, 16 Jun 2025 10:00:00 +0000

"Shoulda Bet More" is your go-to sports betting podcast hosted by Will Hill. From NBA buzzer-beaters to MLB home runs and everything in between, Will breaks down the latest action, hottest takes, and sharpest plays across the sports world. Tune in, get the edge, and maybe next time… you shoulda bet more.

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Shoulda Bet More with Will Hill - Ep. 221 - Ben Wilson

Bill@vsin.com (GoldBoys.com) — Fri, 13 Jun 2025 10:00:00 +0000

The College World Series begins today, and we have invited Ben Wilson (@Ben_Wilson_1) from ESPN+, FOX, and VSiN back to the podcast to give us the rundown. We discuss which of the 8 teams has the best path to the National Championship, which team can surprise, and which team we think will win it all. We also go over each of the first round games beginning today for our favorite bets! We also recap and react to Indiana's win in game 3 of the NBA Playoffs. Have they taken control of the series or is it still going to the Thunder's way? Plus, will Giannis stay with the Bucks after all the rumors surrounding him?

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Shoulda Bet More with Will Hill - Ep. 220 - Sammy P

Bill@vsin.com (GoldBoys.com) — Wed, 11 Jun 2025 10:00:00 +0000

With the College World Series upon us on Friday, we bring on Sammy P (@spshoot) of the Chicken Dinner podcast and Fox Sports to give us a preview of the final 8 teams! We go through each of the teams and we give our favorite plays to win it all and discuss the underdogs that are worth a shot. We discuss Fanduel's new 50 cent tax on Illinois better and whether or not it will discourage users from using Fanduel. Will other books begin charging the tax? We also touch on the state of the NBA Finals and the Stanley Cup Finals and talk about our favorite bets that can be placed at this point in the series. We also have US Open preview in golf that you can get some bets in with!

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Shoulda Bet More with Will Hill - Ep. 219 - Ricky G

Bill@vsin.com (GoldBoys.com) — Mon, 9 Jun 2025 10:00:00 +0000

On today's episode we bring in NBA Twitter legend, Ricky G (@jrichardgoodman), to talk the NBA Finals after the Thunder have evened up the series against the Pacers. Is this dominant win the beginning of the end of the series? Will the Pacers be able to conjure up more comeback magic? We preview game 3 and discuss if the Thunder can finally cover on the road in the playoffs. We talk a little offseason to see where we think superstars like Kevin Durant and Giannis Antetokounmpo end up. Also, was Tom Thibodeau's firing by the Knicks deserved? Who is going to replace him? We also talk about the amazing French Open final yesterday and the Red Sox taking 2 of 3 from the Yankees over the weekend.

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Shoulda Bet More with Will Hill - Ep. 218 - Jonathan Von Tobel

Bill@vsin.com (GoldBoys.com) — Fri, 6 Jun 2025 10:00:00 +0000

The Indiana Pacers pull off another playoff comeback! With Tyrese Haliburton hitting a last second shot to put the Pacers up by a point, the Pacers have taken a 1-0 series lead over the Thunder. We have an instant reaction feature Jonathan Von Tobel (@meJVT) of VSiN Primetime as he returns to the podcast! We recap game 1 and detail how the Pacers were able to comeback in the 4th quarter and how they have been doing it all throughout the playoffs. How will this game affect the series going forward? Should the Thunder still be a heavy favorite, or will the books begin to respect the Pacers? Tune in to see how we think the rest of this series goes and how you should bet it!

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Shoulda Bet More with Will Hill - Ep. 217 - Mitch Moss

Bill@vsin.com (GoldBoys.com) — Wed, 4 Jun 2025 10:00:00 +0000

Today, we touch on a little of everything with Mitch Moss (@MitchMossRadio) from VSiN! We talk some baseball and get a snapshot of where we are this season. Is it a viable betting strategy to bet on the Rockies losing? Which division races are the most intriguing this season? Are we going to see Ohtani pitch this season? Which teams do we think will end up making the playoffs in each League? We also touch on where we are at for end of season awards. We recap the wild first weekend in the NCAA Baseball Tournament as well as betting previews for the NBA Finals and the Stanley Cup Finals!

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Shoulda Bet More with Will Hill - Ep. 216 - Will Hill!

Bill@vsin.com (GoldBoys.com) — Mon, 2 Jun 2025 10:00:00 +0000

You read the title right, today is just Will! Will recaps a Game 6 of the ECF that saw the Pacers put away the Knicks and advance to face the Thunder in the NBA Finals. He go over what the Knicks will need to do in the upcoming offseason to try to get over the hump. Will also previews the NBA Finals and is there any chance that the Pacers pull off what may be the upset of a lifetime? Will also talks baseball. He goes over where we are at the start of June in the MLB. He goes over bets that are worth taking for division winners, teams to make the playoffs, season awards, the Rockies futility, and more!

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Shoulda Bet More with Will Hill - Ep. 215 - Matt Grissom

Bill@vsin.com (GoldBoys.com) — Fri, 30 May 2025 10:00:00 +0000

The NCAA Baseball Tournament begins this weekend as start the road to Omaha and the College World Series. To get us ready for the entire tournament, we've brought back Matt Grissom (@GrissomOnX) of CollegeBaseballInsiders.com and VSiN! We go over the College Baseball season to see how we got here and who the favorites are heading into the tournament. We go through the regionals to see who we like to advance to the Super Regionals and if we think any underdogs can advance. We go through some of our favorite bets to reach the College World Series and we also discuss how the NCAA can better promote the game so as to get more attention during the regular season. Will also recaps Game 5 of the Eastern Conference Final in the NBA and previews this weekend's Yankees/Dodgers World Series rematch series!

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Shoulda Bet More with Will Hill - Ep. 214 - Kelley Bydlon

Bill@vsin.com (GoldBoys.com) — Wed, 28 May 2025 10:00:00 +0000

Both NBA Conference Finals series may nearly be over. With both series being 3-1 in favor of the Thunder and Pacers, we bring Kelley Bydlon (@KelleyBydlon) of VSiN's "A Numbers Game!" to get his opinion on each series. Is there any chance we see each series extended? Are either the Knicks or the Timberwolves worth a bet to come back from these longshot odds? Will the Thunder even lose a game for the rest of this postseason? Tune in to see what we think and to get an edge on the books.

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Shoulda Bet More with Will Hill - Ep. 213 - Gill Alexander

Bill@vsin.com (GoldBoys.com) — Mon, 26 May 2025 10:00:00 +0000

On today's episode, we get a snapshot of where we are at in the Conference Finals with Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod!" We go over the Knicks stunning rally against the Pacers as we finally have a series. Do we think the Knicks can take advantage or is this just a speed bump for the Pacers? We also touch on whether or not the Thunder can take a stranglehold on their series against the Timberwolves. We talk a little Tennis with the upcoming French Open. Gill gives us some of his favorite futures from the event and some of the other plays he's looking at. Plus, we talk about the dreadful Rockies. How much farther can they fall and at what line would we take their over win total on the season?

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Shoulda Bet More with Will Hill - Ep. 212 - Brad Thomas

Bill@vsin.com (GoldBoys.com) — Fri, 23 May 2025 10:00:00 +0000

Wednesday night had one of the craziest NBA games we've ever seen in Game 1 of the Eastern Conference Final between the Pacers and the Knicks and we have to react to what we saw. To get his opinion on the game and the series moving forward, we invite Brad Thomas (@MrBradThomas) from NBC Sports back to the pod! How were the Pacers able to come back in that game, what did the Knicks do wrong that made them choke their lead? Will the Knicks be able to recover from this game or is it the Pacers' series moving forward? In the West, is there anything that will stop the Thunder, or will the Timberwolves be able to show some fight? We also talk some offseason College Football with Brad as it comes faster than you expect. We get his offseason betting approach and some win totals that he is looking to bet for the upcoming season!

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Shoulda Bet More with Will Hill - Ep. 211 - Dustin Swedelson

Bill@vsin.com (GoldBoys.com) — Wed, 21 May 2025 10:00:00 +0000

Shoulda Bet More is your go-to sports betting hangout. This episode we dive into the latest Knicks vs. Pacers action, MLB highlights, and fresh takes on the future NFL schedule. Plus, get early insights and hot takes on future NBA Finals bets. If you’ve ever said, “Man, I shoulda bet more,” this pod’s for you.

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Shoulda Bet More with Will Hill - Ep. 210 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Mon, 19 May 2025 10:00:00 +0000

Shoulda Bet More dives into the hottest topics in sports and sports betting. This episode breaks down the NBA Finals, the Mets vs. Yankees Subway Series, and some heated NHL playoff action. Whether you're a die-hard fan or just here for the odds, we've got picks, predictions, and plenty of takes you shoulda bet more on.

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Shoulda Bet More with Will Hill - Ep. 209

Bill@vsin.com (GoldBoys.com) — Fri, 16 May 2025 15:08:49 +0000

Shoulda Bet More dives into the upcoming NFL schedule and the latest action from the NBA Semifinals. If you're into bold predictions, near-miss bets, and smart takes on what's next in sports, this is your weekly fix.

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Shoulda Bet More with Will Hill - Ep. 208 - Jonathan Von Tobel

Bill@vsin.com (GoldBoys.com) — Wed, 14 May 2025 10:00:00 +0000

On today's episode we continue our talk on the NBA Playoffs with one of our favorite guests, Jonathan Von Tobel (@meJVT) of VSiN Primetime! After a huge win by the Warriors, do we think they can close out their series against the Nuggets on the road? After Indiana stunned the top seeded Cavaliers in the East, what do we think of their chances going forward in the playoffs? Do the Celtics have any chance of prolonging their series against the Knicks tonight? Is there any hope for the Curry-less Warriors against the Timberwolves? JVT and Will discuss their favorite bets heading into tonight's games, and a potential Conference Finals. Plus, is the NBA Draft Lottery rigged or is it rightly stopping tanking?

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Shoulda Bet More with Will Hill - Ep. 207 - Dave Ross

Bill@vsin.com (GoldBoys.com) — Mon, 12 May 2025 10:00:00 +0000

On today's episode, we catch up with all things sports with Dave Ross (@drosssports) of VSiN! We recap the second round of the NBA Playoffs so far and look to see if we can find value in any underdogs in each series. Do the Knicks stand a chance or are the Celtics back? Is there a path for the Warriors without Steph Curry? Is Nuggets/Thunder going to go the distance? We also get Dave's insight on the NHL playoffs. Is the best team in the East not the top seed? Is Vegas worth a bet to win the series after a dramatic last second goal brought them back in the series? We also discuss a little MLB to look at the big picture this far into the season. The Rockies fired their manager Bud Black, is it really his fault though? Do they reach 40 wins this season? Who is the most disappointing team thus far and which team could make a surprise push? Finally, we also talk a little UFC and PGA to round out all of Dave's knowledge!

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Shoulda Bet More with Will Hill - Ep. 206 - Adam Kaufman

Bill@vsin.com (GoldBoys.com) — Fri, 9 May 2025 10:00:00 +0000

What is going on right now in Boston is stunning. The Knicks have taken a 2-0 series lead over the Celtics and to talk about it and the rest of the NBA Playoffs, we've invited back from WKRO 680 and iHeartRadio Boston, Adam Kaufman (@AdamMKaufman)! We talk about what has happened to Boston, how have they melted down in consecutive games that they have had 20 point leads in? Will this be sustainable for the Knicks? Will Porzingis be able to play at 100%? Are the Celtics finally starting to feel the pressure? We also talk about the other shocking 2-0 series as the Pacers are up going back home over the Cavs. Do we think the Pacers can pull off the series upset? Plus, is it inevitable that we are headed for 7 games in Denver/OKC?

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Shoulda Bet More with Will Hill - Ep. 205 - John Jastremski

Bill@vsin.com (GoldBoys.com) — Wed, 7 May 2025 10:00:00 +0000

On today's episode, we talk the NBA Playoffs with our good friend John Jastremski (@john_jastremski) of The Ringer! We go over what was a surprising game 1's for the underdog Nuggets and Knicks! Do either of those teams have any chance of upsetting the favorites? What lessons can we takeaway from the first round? We also give you our favorite plays for each of the game 2's on Wednesday! We also talk MLB to see a state of the league through a month. Who are the best teams in the American League? Which team in the National League will be left out of the postseason come October? Finally, we discuss which team is right now the best in the MLB.

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Shoulda Bet More with Will Hill - Ep. 204 - Kelley Bydlon

Bill@vsin.com (GoldBoys.com) — Mon, 5 May 2025 10:00:00 +0000

The first round of the NBA playoff is all wrapped up and we look towards round two with Kelley Bydlon (@KelleyBydlon) of VSiN's "A Numbers Game!" Will and Kelly react to game 7 between the Warriors and the Rockets to see how Golden State ended up advancing. We then preview each series in the second round to try to bet on which team wins the series and in how many games. We try to predict the rest of the playoffs from the teams remaining. Plus, with the NBA Draft Lottery coming up, where would we like to see Cooper Flagg end up in the NBA?

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Shoulda Bet More with Will Hill - Ep. 203 - Mike Somich

Bill@vsin.com (GoldBoys.com) — Fri, 2 May 2025 10:00:00 +0000

The race for the Triple Crown begins tomorrow with the Kentucky Derby! To get you ready to bet this event, we've brought on the host of 'Ready, Set, Bet' on VSiN, Mike Somich (@Somobomb18)! We discuss what to expect from the race, whether or not the favorite is worth betting on, horses to stay away from, and the longshot that might pay out huge! We also discuss some of the races taking place today at Churchill Downs to get an edge on some of the less bet races. Plus Will recaps where we are at in the NBA playoffs and we take a look at where we are in the NHL Playoffs as well!

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Shoulda Bet More with Will Hill - Ep. 202 - NicLarson

Bill@vsin.com (GoldBoys.com) — Wed, 30 Apr 2025 10:00:00 +0000

We are a month into baseball season, so we though it would be a great time to bring back NicLarson (@NicLarsonGB) from GoldBoys! We talk about which teams have surprised and disappointed us so far this season. How do you handicap a weak American League this year? What longshot teams are worth betting to make the playoffs? Where are we in the race for the Cy Young? We get Nic's go-to markets this season for making money and how he has been making money off of some of the overrated/underrated pitchers in the league. We also touch on whether or not the Rockies can make even 40 wins this season and what is the franchise's plan? We also discuss some of our takeaways of the NFL Draft. Plus, Will updates us on where we are at in the NBA playoffs and weighs in on the NBA vs. NHL Playoffs debate.

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Shoulda Bet More with Will Hill - Ep. 201 - Geoff Schwartz

Bill@vsin.com (GoldBoys.com) — Mon, 28 Apr 2025 10:00:00 +0000

Host Will Hill is joined by former NFL lineman Geoff Schwartz to break down the latest in the NBA and NHL playoffs, share insights on the NFL Draft, and talk all things sports betting. Sharp takes, big opinions, and a little bit of hindsight – don't miss it!

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Shoulda Bet More with Will Hill - Ep. 200 - Gill Alexander

Bill@vsin.com (GoldBoys.com) — Fri, 25 Apr 2025 10:00:00 +0000

Shoulda Bet More is your go-to pod for smart sports talk with just the right amount of hindsight. Hosted by Will Hill, this episode breaks down the biggest surprises and steals of the NFL Draft first round, then shifts focus to what's heating up in the NBA Playoffs. Whether you’re kicking yourself for not betting more or planning your next move, we’ve got you covered.

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Shoulda Bet More with Will Hill - Ep. 199 - Drew Dinsick

Bill@vsin.com (GoldBoys.com) — Wed, 23 Apr 2025 10:00:00 +0000

It's finally time for the NFL Draft! This episode, we get you completely ready for the first round on Thursday night by bringing back Drew Dinsick (@whale_capper) of NBC Sports to the pod! What are the chances that we see any major surprises in the top 4 picks of the draft? We dive into the murkier 5-10 picks of the first round to see what longshot picks that we think some teams could make. We also talk about what positions we expect to slide in the draft and which positions will see more picks than expected on Thursday. Plus we recap each of the series so far in the NBA Playoff and give you our favorite picks for today's games and discuss whether some series underdogs are worth taking at this point!

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Shoulda Bet More with Will Hill - Ep. 198 - Raheem Palmer

Bill@vsin.com (GoldBoys.com) — Mon, 21 Apr 2025 10:00:00 +0000

The NBA Playoffs have officially begun this past weekend and we brought Raheem Palmer from The Ringer (@iamrahstradamus) back to the pod to discuss what we've saw! We recap this past weekend's game 1's and talk about what surprised us and what, if any, thoughts we had coming into the series have changed. We also give you our favorite bets for the upcoming game 2's. Also, if the Bucks lose in the first round, what will they end up doing with Giannis? Will the Thunder go on to sweep the Grizzlies or will the Grizzlies be able to put up any fight? Plus, we discuss what the 76ers do moving forward into the offseason, will Embiid ever be able to play going forward?

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Shoulda Bet More with Will Hill - Ep. 197 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Fri, 18 Apr 2025 10:00:00 +0000

On today's episode, we touch on a little of everything with Jeff Parles (@jeffparles) of "Sports By The Book!" Jeff and Will discuss the first round of the NBA Playoffs to get their opinions on the best series prices and where we can find value from this weekend's games to the Finals. We also talk some baseball as we get Jeff's reactions to the first month of the season. Are the Giants for real and could they murky the waters of the National League playoff picture? Do any teams from the American League pose a threat? Plus, we also touch on next week's NFL Draft and NFL season win totals that may be worth getting in before the draft changes some prices!

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Shoulda Bet More with Will Hill - Ep. 196 - Sammy P

Bill@vsin.com (GoldBoys.com) — Wed, 16 Apr 2025 10:00:00 +0000

We've finished the first pair of NBA Play-In games, today we get you ready for the 2nd pair and the first round of the playoffs! To give his insight, we've brought back from the Chicken Dinner podcast and Fox Sports, Sammy P (@spshoot)! We go over tonight's games and give you our perspective of where we see the best value. We also look at the series prices for the first round matchups and give you our favorite plays for the series as well as the first games! Plus, with the NFL Draft coming up faster than you expect, we begin to take a deeper dive on where we think players will land!

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Shoulda Bet More with Will Hill - Ep. 195 - Jonathan Von Tobel

Bill@vsin.com (GoldBoys.com) — Mon, 14 Apr 2025 10:00:00 +0000

The NBA Playoffs are set and we begin them this week! To get us ready, we've invited back Jonathan Von Tobel (@meJVT) of VSiN Primetime to the pod! We go through each first round series and the play-in games to give you our takes on how we think they will play out and what bets we see that are great value! We also recap the Master's from over the weekend as JVT and Will also give a live reaction during their interview of the playoff. We also discuss the NFL Draft as we inch closer, are there any bets to be made that would give some great value!

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Shoulda Bet More with Will Hill - Ep. 194 - Aaron Schatz

Bill@vsin.com (GoldBoys.com) — Fri, 11 Apr 2025 10:00:00 +0000

On today's episode of Shoulda Bet More, we look towards to upcoming NFL Draft by inviting back Aaron Schatz (@ASchatzNFL) of FTN Fantasy to the pod! We discuss upcoming win total bets to see what teams will overpreform or underpreform their win totals. Can the potential top picks in the draft help turn around those team's projections? Will also goes division by division in the MLB to see the state of some teams at almost a month into the MLB season to see if there are any value bets worth taking!

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Shoulda Bet More with Will Hill - Ep. 193 - Kelley Bydlon

Bill@vsin.com (GoldBoys.com) — Wed, 9 Apr 2025 10:00:00 +0000

Join host Will Hill and guest Kelley Bydlon on Shoulda Bet More, where they dive into the excitement of the Masters and the NBA playoffs. With expert insights, betting tips, and plenty of banter, they’ll break down the latest action and make you feel like you should’ve bet more!

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Shoulda Bet More with Will Hill - Ep. 192 - Matt Youmans

Bill@vsin.com (GoldBoys.com) — Mon, 7 Apr 2025 10:00:00 +0000

We started with 68 and now we are down to 2, Florida vs. Houston. To get you ready for the National Championship game, we've brought back Matt Youmans (@mattyoumans247) of VSiN! We go over how we got here, including Duke's epic collapse against Houston. We preview the game by giving your our analysis of each teams strengths and where they can shine. We also give you our favorite bets in this game and who we think will become champion! We also get Matt's longshots and winners for the upcoming Masters Tournament and his takeaways from the first week of the MLB season!

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Shoulda Bet More with Will Hill - Ep. 191 - Kiev O'Neil

Bill@vsin.com (GoldBoys.com) — Fri, 4 Apr 2025 10:00:00 +0000

Join Will Hill and special guest Kiev O'Neil for a thrilling episode as they dive into the excitement of Final Four weekend in college basketball! They'll break down the high-stakes action, along with some early MLB talk and a sneak peek at the upcoming NFL season. Tune in for expert analysis, hot takes, and all things sports!

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Shoulda Bet More with Will Hill - Ep. 190 - Todd Wishnev

Bill@vsin.com (GoldBoys.com) — Wed, 2 Apr 2025 10:00:00 +0000

We are drawing closer to the Final Four this weekend. To get you ready for the weekend's games, we've brought back Todd Wishnev (@TWishnev)! We discuss Houston vs. Duke and Florida vs. Auburn and give you our favorite bets for the games and Todd gives out his championship pick from the four remaining teams. We talk Women's Final Four as well to give you our favorite picks from that field. We also discuss a little baseball as Todd gives us his favorite betting looks so far after the first week. Will also gives a bit of a NFL Draft preview as well as discussing what bets could be triggered for season long win totals!

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Shoulda Bet More with Will Hill - Ep. 189 - "The Bear" Chris Fallica

Bill@vsin.com (GoldBoys.com) — Mon, 31 Mar 2025 10:00:00 +0000

We have our Final Four! For the first time since 2008, the four remaining teams are all 1 seeds. We are gonna get some competitive matchups and we are here to help you get an edge to bet them! We've brought back "The Bear" Chris Fallica from Fox Sports to go over the matchups! We recap what we just saw this weekend and talk about what gives each of the remaining teams the best chance to win it all. We also discuss the opening weekend in MLB and see if some unexpected starts from certain teams have triggered any season long bets. We also touch on the upcoming NFL Draft and the Women's Basketball Final Four for any sneaky bets that can be placed on those events!

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Shoulda Bet More with Will Hill - Ep. 188 - Gill Alexander

Bill@vsin.com (GoldBoys.com) — Fri, 28 Mar 2025 10:00:00 +0000

On today's episode of Shoulda Bet More, we bright back Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" to go over everything that happened in basketball and baseball yesterday, and what to look forward to this weekend! We discuss yesterday's Sweet Sixteen games including the wild Arkansas/Texas Tech game and give you our favorite bets on the second half of the games today. We also discuss the Saturday Elite Eight games and give you our predictions and analysis to find out who will go to the Final Four! We also go over the big stories from Opening Day and see if any of our opinions have changed. Plus, Will and Gil talk a little White Lotus to cap off the interview!

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Shoulda Bet More with Will Hill - Ep. 187 - NicLarson

Bill@vsin.com (GoldBoys.com) — Wed, 26 Mar 2025 10:00:00 +0000

Tomorrow is Opening Day of the MLB Regular Season! To get you ready, we've brought NicLarson (@NicLarsonGB) from GoldBoys onto the show! We discuss every betting angle you'll want for this upcoming season from World Series futures to end of season awards! Which teams do we think will blow past their projected win totals? Which teams will end up struggling? We also go over some of the Opening Day matchups to give your our favorite bets for the day! Will also looks forward to the Sweet Sixteen matchups on Thursday and gives you his best bets and his predictions on how the games will end up going.

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Shoulda Bet More with Will Hill - Ep. 186 - Jonathan Von Tobel

Bill@vsin.com (GoldBoys.com) — Mon, 24 Mar 2025 10:00:00 +0000

With the first weekend of the NCAA Tournament behind us, we've invited back Jonathan Von Tobel (@meJVT) of VSiN Primetime to get his and Will's reactions to what we all have seen. We recap each region of the bracket and go over what amazed us, what we expected to happen, and what has surprised us about the first two rounds of the tournament. We also take an early look at next weekend for the Sweet Sixteen and the Elite Eight so you can get a head start against the books!

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Shoulda Bet More with Will Hill - Ep. 185 - Stuckey

Bill@vsin.com (GoldBoys.com) — Fri, 21 Mar 2025 10:00:00 +0000

Join host Will Hill and Guest Stuckey as they break down Day 1 of the NCAA Tournament and look ahead to the entire weekend. From key matchups to upsets and predictions, They will give their take on the latest action and what bettors should be watching. If you missed out on the big plays, you’ll definitely be saying, “Shoulda bet more.”

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Shoulda Bet More with Will Hill - Ep. 184 - Iain MacMillan

Bill@vsin.com (GoldBoys.com) — Wed, 19 Mar 2025 10:00:00 +0000

It is finally time. The tournament is set, the matchups made, and we are ready to begin March Madness! To celebrate and get you ready for the first round, we've brought back Iain MacMillan (@IainMacBets) of Sports Illustrated to the pod! Will and Iain go through their favorite matchups that they can get an edge on against the books. Are there any high seeded teams that should be on upset alert this first round? Is there any chance of the number one overall seed, Auburn, losing in the first two rounds? Will and Iain also give their Final Four picks and talk about if there is any chance we see a Cinderella this year!

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Shoulda Bet More with Will Hill - Ep. 183 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Mon, 17 Mar 2025 10:00:00 +0000

Welcome to Shoulda Bet More. Hosted by Will Hill, we dive into the chaos and excitement of Selection Sunday and the madness that follows. From the best bets to the hottest futures, Will breaks down everything you need to know to stay ahead of the game. Whether you're looking to get the inside scoop on this year's tournament or make smarter bets on March Madness, this podcast is your go-to guide. Tune in for expert analysis, strategic picks, and plenty of advice on how not to miss out on the action—because you shoulda bet more.

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Shoulda Bet More with Will Hill - Ep. 182 - Ian Eagle

Bill@vsin.com (GoldBoys.com) — Fri, 14 Mar 2025 10:00:00 +0000

We are heading into the weekend of selection Sunday and we are going to get you prepped for the end of conference tournaments and the start of March Madness! To discuss the NCAA tournament we've brought on the voice of it, from CBS Sports, Ian Eagle! We recap the big stories from the major conference tournaments so far. We discuss the teams that have the best shot of winning the tournament and why they do. We also discuss the sleepers of the tournament and who teams should not take lightly. We also talk about what is defined as a successful season for some coaches/schools and which teams in the tournament are playing with house money. We also touch on the NBA to get Ian's takes on who we may see in the NBA Final this year, plus his reaction on "The Trade" and how he thinks it will go down in NBA history. As an extra bonus, Ian gives his takes on NFL Free Agency so far!

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Shoulda Bet More with Will Hill - Ep. 181 - Reed Wallach

Bill@vsin.com (GoldBoys.com) — Wed, 12 Mar 2025 10:00:00 +0000

It's week two of Conference Tournament week in college basketball and we've bought back Reed Wallach (@ReedWallach) of The Early Reed Podcast and Sports Illustrated for the second week in a row to go over all the power conferences and mid-majors that start their tournaments this week. We go over every conference to look at the high value teams that have a great price on them to go all the way and punch their ticket to the NCAA Tournament. We also look at the teams on the bubble to see what they have to do to be on the right side of the bubble on Selection Sunday. Also, Will recaps the first two days of NFL Free Agency to see if any players are going to change their new team's fortunes this upcoming season!

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Shoulda Bet More with Will Hill - Ep. 180 - Dave Ross

Bill@vsin.com (GoldBoys.com) — Mon, 10 Mar 2025 10:00:00 +0000

To start your betting week right, we've invited back Dave Ross (@drosssports) of VSiN to go over everything going on in the sports betting world! We talk with Dave about baseball and the Gerrit Cole news that has rocked the Yankees. With Cole possibly needing Tommy John Surgery, how does this affect their AL East division prices and is it worth it to bet any of the other teams in the division? We also touch on some of Dave's favorite futures around the league. We also talk some NFL offseason as well as looking at Dave's favorite in the NCAA Tournament. Will also recaps the tournaments that wrapped up over the weekend and who already has their tickets punched to March Madness.

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Shoulda Bet More with Will Hill - Ep. 179 - John Laghezza

Bill@vsin.com (GoldBoys.com) — Fri, 7 Mar 2025 11:00:00 +0000

On today's episode, we do a deep dive into the upcoming baseball season with John Laghezza (@JohnLaghezza) of The Athletic! We pick John's brain about his process for making preseason baseball bets and how he uses fantasy baseball as a tool. We get his favorite futures as well as win totals that he sees as mispriced. We go through what look to be the most competitive divisions in the MLB this season as John gives us his takes on the teams involved. Are the Yankees no longer the kings of the AL East? Will the Braves rotation carry them through the NL East? Plus, Will gives us an updated look on conference tournaments before the big conferences start next week!

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Shoulda Bet More with Will Hill - Ep. 178 - Reed Wallach

Bill@vsin.com (GoldBoys.com) — Wed, 5 Mar 2025 11:00:00 +0000

On today's episode, we continue our mid-major conference tournament coverage by bringing back Reed Wallach (@ReedWallach) of The Early Reed Podcast and Sports Illustrated! We go through what has transpired so far and what we think is to come of the smaller conferences from the Atlantic Sun to the West Coast Conference. We also get Reed's take on NCAA Tournament Sleepers, NBA awards as we inch closer to the playoffs, and his take on the Mets win total this season!

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Shoulda Bet More with Will Hill - Ep. 177 - Kiev O'Neil

Bill@vsin.com (GoldBoys.com) — Mon, 3 Mar 2025 11:00:00 +0000

It is finally March and conference tournaments begin this week. To celebrate, we get you ready for conference tournament betting with Kiev O'Neil (@OBKiev) of The Odds Breakers! We recap this weekend in college basketball by discussing what happened to Alabama as they got upset with a last second shot by Tennessee. We look towards some of the mid-major tournaments and discuss some of the wacky brackets and what longshots could win those tournaments and steal a bid to the NCAA tournament. Plus we go over our sleepers and longshots to go far in the NCAA Tournament. Tournament time is a fantastic time to bet, and we are here to help you win big so tune in!

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Shoulda Bet More with Will Hill - Ep. 176 - Jonathan Von Tobel

Bill@vsin.com (GoldBoys.com) — Fri, 28 Feb 2025 11:00:00 +0000

Today we bring back one of our favorite guests, Jonathan Von Tobel (@meJVT) of VSiN Primetime! We talk a little NBA to see where everything is at post All-Star Break and trade deadline. Are the Lakers a contender after a few games with Luka? Can they or anyone else in the west threaten OKC in the playoffs? Are the Knicks a legitimate contender in the East? After the news about Joel Embiid, what is the Sixers path now for this season? We also talk a little NFL as we discuss the recent news of Matt Stafford meetings and talk where QBs go in this offseason of QB musical chairs.

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Shoulda Bet More with Will Hill - Ep. 175 - Mitch Moss

Bill@vsin.com (GoldBoys.com) — Wed, 26 Feb 2025 11:00:00 +0000

We continue to get ready for the upcoming MLB season on today's episode by inviting back from VSiN, Mitch Moss (@MitchMossRadio)! Mitch fills us in on his favorite longshots of this upcoming season that have the potential to cash out big! He also gives us his favorite sleeper teams, his favorite win total bet, and a surprising pick to get the most home runs this season! Plus, Mitch tells us of his epic video poker win that paid out huge! Will also recaps what has been a tough spring training so far for the Mets with some pitcher injuries and how they may still be worth a division winner bet.

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Shoulda Bet More with Will Hill - Ep. 174 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Mon, 24 Feb 2025 11:00:00 +0000

Welcome to Shoulda Bet More, the podcast where host Will Hill and guest Jeff Parles dive deep into everything sports! From college basketball and the NBA to the upcoming MLB season and all the latest NFL rumors, they cover it all with insightful takes and plenty of banter. Tune in for your weekly fix of sports talk, analysis, and a touch of humor!

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Shoulda Bet More with Will Hill - Ep. 173 - John Jastremski

Bill@vsin.com (GoldBoys.com) — Fri, 21 Feb 2025 11:00:00 +0000

Today, we continue getting ready for baseball at the beginning of Spring Training and we brought back John Jastremski (@john_jastremski) of The Ringer to get his thoughts on the upcoming season! We discuss the AL and NL East as they figure to be the divisions that could go down to the wire this season and try to project who will come out on top. We also discuss win totals for some of those teams to see if they are worth betting. We take a broader look at the league as well to see who some of the sleeper teams to win divisions and the World Series are. We also touch base on some NFL offseason, as well as 2nd half NBA and a little March Madness!

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Shoulda Bet More with Will Hill - Ep. 172 - Dustin Swedelson

Bill@vsin.com (GoldBoys.com) — Wed, 19 Feb 2025 11:00:00 +0000

On today's episode of Shoulda Bet More, we start talking baseball with Dustin Swedelson (@dustinswedelson) from SiriusXM Mad Dog Sports Radio and VSiN! We get his takes on who the best teams are in the AL and the NL, the sleepers in the divisions, and his favorite longshots to win the World Series! We go over offseason questions for the Mets, Yankees, Red Sox, and more and see if they've improved enough to be major forces this season. We also touch on the NFL offseason to take a temperature on where certain QBs will end up and if they can improve these QB needy teams. Will also goes over what has become a broken NBA All-Star weekend and looks at the 2nd half of the NBA season!

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Shoulda Bet More with Will Hill - Ep. 171 - Todd Wishnev

Bill@vsin.com (GoldBoys.com) — Mon, 17 Feb 2025 11:00:00 +0000

We are just weeks away from conference tournaments and the NCAA Tournament to crown the champion of college basketball. To get us ready for the postseason, we've invited Todd Wishnev (@TWishnev) back to the pod! We recap the Auburn vs. Alabama game from the weekend and discuss whether or not anyone can stop Auburn or if they are just too dominant. We talk about some of the top teams from each of the conferences and wonder how far in the tournament they can go and what weakness could prevent them from advancing. We also talk about the sleepers from the power conferences and the mid-majors that can shake up the tournament and send a powerhouse packing. We also get you ready for some of the major games tonight so you can take advantage of the books.

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Shoulda Bet More with Will Hill - Ep. 170 - Brad Thomas

Bill@vsin.com (GoldBoys.com) — Fri, 14 Feb 2025 11:00:00 +0000

The Genesis Open in LA is this weekend, and to get some advice on how to bet it, we've brought Brad Thomas (@MrBradThomas) from NBC Sports and MGM Network back to the podcast! We pick his brain about who he likes to win the tournament and who he thinks is worth a flier. We also get his opinions on what has changed in the NBA after the trade deadline and if any team can stop the Thunder and Celtics from ending up in the Finals. We also talk a little NFL offseason and whether or not older QB such as Rogers, Stafford, and Cousins end up with any teams next year.

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Shoulda Bet More with Will Hill - Ep. 169 - Geoff Schwartz

Bill@vsin.com (GoldBoys.com) — Wed, 12 Feb 2025 11:00:00 +0000

On today's episode of Shoulda Bet More, we continue to dive into the Super Bowl postmortem. Who better to bring on to talk football than a former NFL Offensive Lineman in Geoff Schwartz (@geoffschwartz) from Fox Sports! We go in-depth on how the Eagles thoroughly dismantled the Chiefs. How much blame should Patrick Mahomes shoulder in the loss? What can we takeaway from the construction of this Eagles roster and what will other teams to do copy its success? We also begin to look forward to next season. who is most likely to go number one overall in the NFL Draft? Where will Aaron Rodgers most likely end up? Will the Chiefs still be the favorites in the AFC next season? Check out the episode to hear our thoughts!

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Shoulda Bet More with Will Hill - Ep. 168 - Gill Alexander

Bill@vsin.com (GoldBoys.com) — Mon, 10 Feb 2025 11:00:00 +0000

The Philadelphia Eagles are your Super Bowl LIX champions, and they won in a dominant fashion. We've invited Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" back to the pod to get his and Will's instant reaction to what we just witnessed. How did the Eagles manage to put away the Chiefs by halftime? Is this the end of the Chiefs dynasty? Do we rethink how truly good some of the other teams around the league are after this performance by the Eagles? We look towards next year where Gill gives us his early bet for the Super Bowl LX winner!

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Shoulda Bet More with Will Hill - Ep. 167 - Sammy P

Bill@vsin.com (GoldBoys.com) — Fri, 7 Feb 2025 11:00:00 +0000

We are just 2 days away from the Super Bowl. We continue our coverage of it today by bringing from the Chicken Dinner podcast, BetMGM, and Fox Sports, Sammy P (@spshoot)! We get Sammy's perspective on how the game will go down and the bets that he is placing because of it. In addition, Will gives the plays that he's locking in for Sunday. We also talk some college basketball to see what sleepers and longshots could go to the Final Four in March. We also discuss some baseball and have a discussion on this season's Rookie of the Year and a sneaky longshot that you can bet!

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Shoulda Bet More with Will Hill - Ep. 166 - Kiev O'Neil

Bill@vsin.com (GoldBoys.com) — Wed, 5 Feb 2025 11:00:00 +0000

Today, we are kicking our Super Bowl coverage into high gear by bringing back Kiev O'Neil (@OBKiev) of The Odds Breakers to the pod! We take a deep dive into Sunday's game by looking at each of the main markets in-depth and the best player props that stick out to us. Kiev gives us his methods of attacking Super Bowl betting so he can end the biggest game of the year on top. We also talk about the best foods to have while watching the Super Bowl! We also get into late season College Basketball! As we get closer to the tournament time, who are the most underrated/overrated teams that you should bet on or stay away from? Also, Will gives his final thoughts about the Luka trade and the Fox to the Spurs trade!

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Shoulda Bet More with Will Hill - Ep. 165 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Mon, 3 Feb 2025 11:00:00 +0000

Welcome to Shoulda Bet More, your go-to podcast for all things sports! In this episode, we dive into the upcoming Super Bowl, breaking down the key matchups and what to expect. Plus, we’re talking about the jaw-dropping NBA trade that’s shaking up the league: Anthony Davis for Luka Dončić. You won’t want to miss this one. Tune in!

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Shoulda Bet More with Will Hill - Ep. 164 - Jason Weingarten

Bill@vsin.com (GoldBoys.com) — Fri, 31 Jan 2025 11:00:00 +0000

We are nearing the date of pitchers and catchers arriving for Spring Training. To get ready for that date, we've brought back Jason Weingarten (@Spreadapedia) of VSiN to give us his outlook on the upcoming season of baseball. We get his reaction to the offseason moves and how he feels about the Dodgers spending money on their free agents. We get Jason's favorite future bets for this season with the offseason coming to a close. We take a quick discussion of awards futures to see if there are any longshots that have a great chance of winning. We also take a look at betting the Caribbean Series that begins today to crown the best club in the Caribbean (and Japan)!

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Shoulda Bet More with Will Hill - Ep. 163 - Kelley Bydlon

Bill@vsin.com (GoldBoys.com) — Wed, 29 Jan 2025 11:00:00 +0000

With the NFL in a hibernation period until the Super Bowl, we turn our eyes to NBA basketball! To get a temperature of where we are at in the middle of the season, we've invited Kelley Bydlon (@KelleyBydlon) from VSiN's "A Numbers Game!" Is a Celtics vs. Thunder Final inevitable? Which teams have the best chance of stopping it come playoffs? What trades could we possibly see as we approach the midseason mark? Plus, who are the front runners for awards and what longshots could surprise? We also touch on Kelley's Super Bowl bets to see what he likes!

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Shoulda Bet More with Will Hill - Ep. 162 - Jonathan Von Tobel (JVT)

Bill@vsin.com (GoldBoys.com) — Mon, 27 Jan 2025 11:00:00 +0000

Shoulda Bet More is the ultimate podcast for NFL fans who love the thrill of the game and the excitement of placing a bet. Join Will Hill and returning guest JVT as they break down the Conference Championship games, analyzing key plays, standout performances, and those crucial moments that made or broke the odds. Get expert takes on the big game, plus insider tips and predictions for the upcoming Super Bowl showdown. Whether you’re a casual fan or a die-hard gambler, Shoulda Bet More is the perfect place to fuel your football fix and prepare for the biggest game of the year!

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Shoulda Bet More with Will Hill - Ep. 161 - Dave Ross

Bill@vsin.com (GoldBoys.com) — Fri, 24 Jan 2025 11:00:00 +0000

It's Conference Championship weekend, and we are continuing to go to VSiN collaborators to get the best in-depth look look at the games by inviting back Dave Ross (@drosssports)! We take a deep dive into the Commanders vs. Eagles and the Bills vs. Chiefs and give you our favorite props and leans. We try to get Dave's picks for the weekend and for who he thinks will win the Super Bowl in two weeks! Lastly, we get Dave's reaction to how the Mets have done this offseason beyond the Juan Soto signing and if he thinks they can win the NL East and beyond.

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Shoulda Bet More with Will Hill - Ep. 160 - Matt Youmans

Bill@vsin.com (GoldBoys.com) — Wed, 22 Jan 2025 11:00:00 +0000

With the National Championship Game in the rear-view, we only have 3 football games remaining. To discuss what we've seen and what we will see, we've brought back from VSiN, Matt Youmans (@mattyoumans247)! We go over Ohio State's victory against Notre Dame to put a bow on a great College Football season. We preview Conference Championship weekend in the NFL by discussing our favorite bets so far with these early lines. Can the Bills finally overcome Patrick Mahomes and Chiefs in the playoffs? Will Jayden Daniels and the Commanders stun the Eagles and go to the Super Bowl? We also go over where we are at in the College Basketball season and if there are any sleepers that could make it to the Final Four. Finally, we discuss what the Dodgers have done and Matt's opinion of what they and the rest of the MLB has done in free agency.

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Shoulda Bet More with Will Hill - Ep. 159 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Mon, 20 Jan 2025 15:42:17 +0000

What a great weekend of football we had, but we aren't done yet! Today is the National Championship game between Ohio State and Notre Dame. To give us his betting looks for the game, we've invited back Jeff Parles (@jeffparles) from "Sports By The Book!" We do a deep dive into the game and give you our favorite to win and our betting leans that show where we think this game is headed. We also recap an awesome divisional round and get into the upsets and controversies from the weekend. Is the Lions window closed after this weekend's brutal loss? Just how much of a problem were the refs in Kansas City? We also take an instant reaction to next week's betting lines and give you our thoughts and feelings on them. Finally, after the Roki Sasaki and Tanner Scott signings by the Dodgers, we take a deep look into how MLB Free Agency has gone and what it means for the future of the sport of baseball.

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Shoulda Bet More with Will Hill - Ep. 158 - John Jastremski

Bill@vsin.com (GoldBoys.com) — Fri, 17 Jan 2025 11:00:00 +0000

It's Divisional Round weekend! To expand on what we were talking about with early previews on Wednesday's episode, we've brought back John Jastremski (@john_jastremski) of The Ringer to give us more betting viewpoints of this weekend's games! We do an in-depth dive on Texans/Chiefs, Commanders/Lions, Rams/Eagles, and Ravens/Bills, giving your our favorite betting looks in each game and who we ultimately think we will be seeing in the Conference Championships! We discuss some of the coaching carousel going around the league's non-playoff teams and say who we think is going to fill vacant head coaching positions. Plus, we get John's take on MLB free agency this far into the offseason and see if he thinks any free agents may give a team an edge this upcoming season!

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Shoulda Bet More with Will Hill - Ep. 134 - Iain MacMillan

Bill@vsin.com (GoldBoys.com) — Wed, 15 Jan 2025 11:00:00 +0000

With the first round of the NFL Playoffs officially in the books, we look forward to the Divisional round. To give us an early look, we've brought back Iain MacMillan (@IainMacBets) of Sports Illustrated to the pod! We react to the Monday night beatdown by the Rams and what that means for the Vikings going forward. Do they keep Sam Darnold, or is the future JJ McCarthy? With the Chiefs' starters not playing in Week 18, have they rested too long? We look at the matchups for this round and discuss how each team matches up to their opponent. Iain also gives us his Super Bowl winner out of the remaining teams!

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Shoulda Bet More with Will Hill - Ep. 156 - Kiev O'Neil

Bill@vsin.com (GoldBoys.com) — Mon, 13 Jan 2025 11:00:00 +0000

Join host Will Hill and returning guest Kiev O'Neil as they break down all the action from NFL's wild-card weekend! From game predictions to big plays, the duo dives deep into what went right, what went wrong, and what they should’ve bet more on. Plus, they look ahead to the high-stakes Monday Night Football matchup and touch on the latest in college football. Whether you're a seasoned bettor or a casual fan, this podcast is packed with insights, analysis, and plenty of laughs. Don’t miss out—tune in for the sharpest takes and the best betting advice around!

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Shoulda Bet More with Will Hill - Ep. 155 - Aaron Schatz

Bill@vsin.com (GoldBoys.com) — Fri, 10 Jan 2025 11:00:00 +0000

The NFL Playoffs are finally here. For the next 3 weeks, we have do or die football that culminates in Super Bowl LIX in February. We are gonna get you started off on the right foot this Wild Card Weekend by bringing back on Aaron Schatz of FTN Fantasy. We'll go in-depth on all of the six games that happen this weekend and give you our opinions on the matchup, who is favored, and our favorite bets for each game. Also, because Aaron is a voter for NFL awards, we attempt to pick his brain about what he and other voters are looking for in the MVP, Coach of the Year, and Comeback Player of the Year awards!

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Shoulda Bet More with Will Hill - Ep. 154 - Brad Powers

Bill@vsin.com (GoldBoys.com) — Wed, 8 Jan 2025 11:00:00 +0000

The College Football Playoff Semifinals are this week and we have all the info you need! Brad Powers (@BradPowers7) of the "Bet the Board Podcast" returns so we can do a deep dive into the Orange Bowl between Notre Dame and Penn St. on Thursday, and the Cotton Bowl between Ohio St. and Texas! We look at the lines and give you our favorite plays from the spread, over/under, and player props! We also preview the hypothetical National Championship lines to get an idea of how the books see each team. We also discuss Brad's pick to win the National Championship. Brad also gives us a mini preview of the Wild Card round in the NFL so you can get ahead before the lines shift!

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Shoulda Bet More with Will Hill - Ep. 153 - Jonathan Von Tobel (JVT)

Bill@vsin.com (GoldBoys.com) — Mon, 6 Jan 2025 11:00:00 +0000

In this episode, Will and his guest break down the thrilling Week 18 of the NFL playoffs, analyzing key games, big upsets, and missed opportunities. Tune in for expert insights, heated debates, and a deep dive into the biggest moments that had fans and bettors on the edge of their seats. Whether you're a seasoned gambler or a football fanatic, this is the place to be for all the action!

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Shoulda Bet More with Will Hill - Ep. 152 - "The Bear" Chris Fallica

Bill@vsin.com (GoldBoys.com) — Fri, 3 Jan 2025 11:00:00 +0000

With the CFP Quarterfinals in the books, we look ahead to the semis. To do that, we've brought back from Fox Sports, "The Bear" Chris Fallica (@chrisfallica)! We discuss our thoughts coming off each game and look forward to what we think the semifinals will look like. We also look forward to Week 18, the last week of the NFL regular season. Will we see Denver solidify the 7th seed, or will the Dolphins or Bengals be a surprise 7th seed? Who will win the 1 seed in the NFC, the Lions or the Vikings? We look at that game and give you our favorite looks at it. We also discuss the most competitive awards and see if there is any value voting for the underdogs.

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Shoulda Bet More with Will Hill - Ep. 151 - Thor Nystrom

Bill@vsin.com (GoldBoys.com) — Tue, 31 Dec 2024 11:00:00 +0000

Today, we've got the big College Football Playoff Quarterfinal podcast for you! We've invited Thor Nystrom of Fantasy Life to give you a betting preview for all four games being played tomorrow. We go in depth on each game and give you our favorite betting leans and why we think they'll happen. We also give hear Thor's favorite to win the National Championship as well as whether or not any upsets happen this week. Also, Will and Thor, who are both Vikings fans, discuss why they should be taken seriously as a Super Bowl threat.

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Shoulda Bet More with Will Hill - Ep. 150 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Mon, 30 Dec 2024 15:12:45 +0000

Join host Will Hill and guest Jeff Parles on Shoulda Bet More, where they dive into the world of sports betting. From NFL and college football insights to a sneak peek at early MLB action, they break down the key games, trends, and predictions you need to make smarter bets. Tune in for sharp analysis, lively debates, and a bit of humor—because when it comes to sports betting, you shoulda bet more!

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Shoulda Bet More with Will Hill - Ep. 149 - Reed Wallach

Bill@vsin.com (GoldBoys.com) — Fri, 27 Dec 2024 11:00:00 +0000

We're now deep into Bowl Season and with a big slate coming up this week, we've invited Reed Wallach (@ReedWallach) of The Early Reed Podcast and Sports Illustrated back to the pod to give us his favorite betting looks! We go over each the bowl games this weekend to find out what our favorite angles to bet are in each of them. We also look ahead to the CFP Quarterfinals next week to get an early look at who we will think make the semis and who could potentially be poised for an upset. Finally, Will looks back on the Christmas Day slate of NFL games, Netflix's production of the event, and looks ahead to the penultimate week in the NFL for his favorite betting looks.

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Shoulda Bet More with Will Hill - Ep. 148 - Gill Alexander

Bill@vsin.com (GoldBoys.com) — Mon, 23 Dec 2024 11:00:00 +0000

Welcome to Shoulda Bet More, where your host, Will Hill and sports betting expert Gill Alexander, break down the biggest moments from the NFL Sunday and dissect a disastrous weekend of College Football. With sharp analysis, insider knowledge, and a touch of humor, they go beyond the scores to give you the insights you need to make smarter bets. Whether it was an unexpected NFL upset or a College Football meltdown, they’ll talk about it all, and of course, they'll let you know why you shoulda bet more! Tune in for your fix of sports betting banter and expert takes.

Don't miss out—if you love the thrill of the game and the art of the wager, this podcast is for you.

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Shoulda Bet More with Will Hill - Ep. 147 - Brad Powers

Bill@vsin.com (GoldBoys.com) — Fri, 20 Dec 2024 11:00:00 +0000

The first 12 team College Football Playoff is finally upon us. Beginning tonight we have the first round on-campus games and we have brought back Brad Powers (@BradPowers7) of the Bet The Board Podcast to give us his betting perspective on the first round and beyond. We go over each game this weekend and let you know our favorite bets and why we expect them to happen. We discuss whether or not we see any upsets this weekend. We also look at the other bowl games being played this weekend to give out our favorite bets. Plus, Will recaps the Thursday Night Football game between the Broncos and the Chargers and asks if Denver is in trouble of missing the playoffs. Will also gives his favorite NFL bets from a two day weekend slate of games!

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Shoulda Bet More with Will Hill - Ep. 146 - Mitch Moss

Bill@vsin.com (GoldBoys.com) — Wed, 18 Dec 2024 11:00:00 +0000

We are heading into a loaded football weekend with the start of the College Football Playoff on Friday all the way through the NFL on Sunday. To break down what we are about to see, we've brought back Mitch Moss (@MitchMossRadio) of VSiN! We talk general NFL as we head towards the end of the regular season with topics like should the Chiefs rest Patrick Mahomes with his injury, should the Broncos and Chargers be worried, and will the Steelers or Ravens win the AFC North? We also talk some last second NFL awards bets and whether or not we might see some underdogs steal some awards. We also look to who our favorite underdogs are for the College Football Playoff and the rest of the bowl season! Plus, Will goes over some of the recent MLB offseason trades and what effect they will have come the regular season.

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Shoulda Bet More with Will Hill - Ep. 145 - Dave Ross

Bill@vsin.com (GoldBoys.com) — Mon, 16 Dec 2024 11:00:00 +0000

On this Monday episode of Shoulda Bet More, we invite Dave Ross (@drosssports) of VSiN back to the pod! We go over everything we just saw this weekend in the NFL. Should the Lions be concerned with their poor defensive performances? What will the Chiefs do about Patrick Mahomes's potential injury? Could we see any surprise playoff teams at the end of the season? We look forward to tonight's Monday Night Football doubleheader and give you the bets that we are looking at. We also talk MLB free agency were Dave, a noted Mets fan, gives his reaction to the Juan Soto signing among the Mets' other moves. Finally, we also talk about what Bill Belichick and Mike Lombardi can do to transform UNC football into a playoff team.

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Shoulda Bet More with Will Hill - Ep. 144 - Jonathan Von Tobel (JVT)

Bill@vsin.com (GoldBoys.com) — Fri, 13 Dec 2024 11:00:00 +0000

Join host Will Hill and guest @meJVT on Shoulda Bet More, your go-to sports betting podcast for sharp picks and candid analysis. In this episode, the duo dives into their top NFL picks for the upcoming Sunday slate, providing insights on which teams to back and why. They’ll also discuss the surprising news of Bill Belichick to the University of North Carolina and what that could mean for the future of the program. Finally, Will and JVT weigh in on the College Football Playoff, breaking down the matchups, potential upsets, and who’s really got the best shot at the title. Whether you're a seasoned bettor or just getting started, Shoulda Bet More gives you the edge you need to make smarter, more informed bets. Tune in for the latest picks, hot takes, and insider knowledge!

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Shoulda Bet More with Will Hill - Ep. 143 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Wed, 11 Dec 2024 11:00:00 +0000

It has been a wild past few days for MLB Free Agency and to help break it down with Will, we've brought back from "Sports By The Book," Jeff Parles (@jeffparles)! We talk about the shockwaves that are still resonating for Yankee fans after losing Juan Soto to the Mets. Are the Mets now the big brother to the Yankees? How should the Yankees proceed in free agency without Soto? Who is now the favorite to win the American League? Will the Mets be able to displace the Dodgers as the favorites in the National League? We look towards some futures for next season to see if anything is in play. Jeff also gives us his take on the College Football Playoff bracket and tells us his favorite betting looks for the first round and the tournament as a whole. Plus, an early week 15 NFL betting preview!

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Shoulda Bet More with Will Hill - Ep. 142 - "The Bear" Chris Fallica

Bill@vsin.com (GoldBoys.com) — Mon, 9 Dec 2024 11:00:00 +0000

The bracket is set. We now know the 12 teams in the College Football Playoff and we've invited back "The Bear" Chris Fallica (@chrisfallica) from Fox Sports to get an instant reaction. Did the committee get it right? Who got snubbed? Who do we think is going to win it all? We talk about all that and take a look at the first round betting lines to see what angles we like before the lines move. We also give our reactions to Week 14 in the NFL and preview Monday Night Football between the Bengals and Cowboys. Will also discusses Juan Soto's megadeal with the New York Mets and what it means for baseball going forward.

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Shoulda Bet More with Will Hill - Ep. 141 - Mike Sando

Bill@vsin.com (GoldBoys.com) — Fri, 6 Dec 2024 11:00:00 +0000

On today's episode of Shoulda Bet More, we invite back Mike Sando (@SandoNFL) of The Athletic to pick his brain on NFL awards. As we draw closer to the end of the season, we talk with Mike to find what he, as a voter, looks for when voting for various awards so we can better understand what voters look for when we place bets on NFL awards. We also talk NFL in general with topics such as his opinion on Week 14's games, whether or not Bryce Young's resurgence is for real, and where will Bill Belichick be coaching next year, if at all? Plus Will recaps Thursday Night Football and gives his favorite bets for Week 14 in the NFL and Conference Championship weekend in College Football!

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Shoulda Bet More with Will Hill - Ep. 140 - Matt Youmans

Bill@vsin.com (GoldBoys.com) — Wed, 4 Dec 2024 11:00:00 +0000

Huge weekend of football is coming up. It's conference championship weekend and there is also a fantastic slate of NFL games this week. To prepare you for betting this slate of games, we've brought back from VSiN, Matt Youmans (@mattyoumans247)! We discuss the College Football Playoff rankings and give you their favorite bets to make the playoff in the final week. Could any upsets this weekend change the final 12 teams in the playoff? We look ahead to a great Thursday Night Football matchup between the Packers and the Lions and give you our leans and what we are looking to bet. We also give you our favorite bets for the rest of the weekend so you can get prepared early in the week!

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Shoulda Bet More with Will Hill - Ep. 139 - Kiev O'Neil

Bill@vsin.com (GoldBoys.com) — Mon, 2 Dec 2024 11:00:00 +0000

On this week’s episode of Shoulda Bet More, He's back! Kiev O'Neil & Will break down the thrilling outcome of Sunday Night Football. Tune in as Kiev gives us his hot takes and analysis on the game’s impact.

We’re also diving deep into the future of college football—what’s next for the sport, the new dynamics, and how upcoming changes might shake things up for players, coaches, and fans alike. Whether you’re a seasoned sports bettor or a casual fan, this episode is packed with insights you won’t want to miss.

Hit play now and let’s talk sports, betting, and everything in between!

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Shoulda Bet More with Will Hill - Ep. 138 - Paul Howard

Bill@vsin.com (GoldBoys.com) — Fri, 29 Nov 2024 11:00:00 +0000

On this Black Friday edition of Shoulda Bet More, we invite a new guest! From Follow the Money on VSiN, Paul Howard (@paulyhoward)! We recap the Thanksgiving games and discuss the puzzling end to the Bears/Lions game where the Bears go home with a timeout in their pocket. We discuss our favorite bets for the rest of week 13 including today's game between the Raiders and the Chiefs. We also talk the College Football Playoff and whether or not a possible 3 loss team could make the playoff. We also give our favorite College Football picks this weekend and how bad would it be for the Yankees to lose Juan Soto to another team in free agency.

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Shoulda Bet More with Will Hill - Ep. 137 - Adam Kaufman

Bill@vsin.com (GoldBoys.com) — Wed, 27 Nov 2024 11:00:00 +0000

Tomorrow is Thanksgiving and we've got the analysis you need so that while you are stuffing your face with turkey, you are also stuffing your wallet with cash from your bets. To go over every game on Thursday, we've brought back from WKRO 680 and iHeartRadio Boston, Adam Kaufman (@AdamMKaufman)! We give our betting angles for Bears vs. Lions, Giants vs. Cowboys, and Dolphins vs. Packers. Adam also gives us a preview of his favorite bets for the rest of Week 13. Plus we discuss the state of the College Football Playoff and Adam gives us his view on Red Sox free agency!

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Shoulda Bet More with Will Hill - Ep. 136 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Mon, 25 Nov 2024 11:00:00 +0000

Coming off what was a wild NFL Sunday with many games turned on their head, we invite Jeff Parles (@jeffparles) from "Sports By The Book" back to the pod! We recap and react to all the games, many of which had late lead switches and improbable plays. We give you our takeaways for what this week means moving forward in the season. We preview the Har-bowl in tonight's Monday Night Football game between the Ravens and the Chargers. We also discuss the College Football Playoff as the field gets clearer as we head towards the final week of conference play. Who do we think the committee will leave in and out? Plus, we discuss Juan Soto's free agency and how is MLB allowing 2 teams to be playing in Minor League ballparks this upcoming season?

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Shoulda Bet More with Will Hill - Ep. 135 - John Jastremski

Bill@vsin.com (GoldBoys.com) — Fri, 22 Nov 2024 11:00:00 +0000

On this episode of Shoulda Bet More, we get you ready for Week 12 in the NFL with John Jastremski (@john_jastremski) of The Ringer returning to the pod! We go over our favorite bets for the weekend so you can get the edge on the books. We do a mid-season check on our futures and awards to see how confident we are that they hit. Also, who do we think ends up getting those last playoff spots when the regular season is all said and done? Also, we talk MLB free agency to figure out where the big name free agents like Juan Soto and Roki Saski sign.

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Shoulda Bet More with Will Hill - Ep. 134 - Iain MacMillan

Bill@vsin.com (GoldBoys.com) — Wed, 20 Nov 2024 11:00:00 +0000

Iain MacMillan (@IainMacBets) of Sports Illustrated returns to the pod on this episode of Shoulda Bet More to talk all things NFL. We discuss where we find value on betting division winners this far into the season. Could the Chargers or the Steelers be surprise Super Bowl contenders? What should the Ravens do about a suddenly human Justin Tucker? Why are there so many bad teams in the NFL? Is there a new contender for Offensive Rookie of the Year? We also preview Thursday Night Football to give you our favorite bets and leans as well as our favorite on the Sunday slate of games! Plus, Will recaps and reactions to the award winners for MLB!

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Shoulda Bet More with Will Hill - Ep. 133 - Doug Kazirian

Bill@vsin.com (GoldBoys.com) — Mon, 18 Nov 2024 11:00:00 +0000

After a weekend with some big NFL matchups, we've brought back Doug Kezirian (@DougKezirian) from OnlyPlayers.com to the pod! We give our reactions to Week 11 in the NFL. What does it mean for the Bills to beat the Chiefs? Can anyone stop the Lions? Are the 49ers in danger of missing the playoffs? We talk about the Coach of the Year and MVP races to see where we can get value in betting. We also talk Monday Night Football between the Texans and Cowboys and give our betting preview of it. Plus, we talk the Jake Paul/Mike Tyson fight and the struggling production issues from Netflix.

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Shoulda Bet More with Will Hill - Ep. 132 - Matkafee

Bill@vsin.com (GoldBoys.com) — Fri, 15 Nov 2024 11:00:00 +0000

Join Will Hill and returning guest @Matkafee as they dive into the world of sports betting, covering the NFL, NBA, and their opinions on some futures awards picks. Get expert analysis, sharp insights, and winning strategies for your next bet, whether you're looking at season-long bets or breaking down upcoming matchups. Tune in for your edge in the game!

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Shoulda Bet More with Will Hill - Ep. 131 - Brad Thomas

Bill@vsin.com (GoldBoys.com) — Wed, 13 Nov 2024 11:00:00 +0000

We only have a few weeks left of College Football, so we've brought back Brad Thomas (@MrBradThomas) from NBC Sports and GoldBoys to discuss where we are as we get closer to the selection of the College Football Playoff! We go over the various scenarios that can get the bubble teams in and the various conference championship games that could affect it. We also go over this week in betting College Football for games tonight through the weekend. Also, after the Miami Dolphins win on Monday, are they back in the playoff race? We also have a TNF betting preview between the Commanders and the Eagles. Who will win the Juan Soto sweepstakes? We discuss these all and more!

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Shoulda Bet More with Will Hill - Ep. 130 - Gill Alexander

Bill@vsin.com (GoldBoys.com) — Mon, 11 Nov 2024 11:00:00 +0000

On this episode of Shoulda Bet More, we have Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" back on the podcast to recap what we saw this weekend in NFL and College Football! We recap Week 10 in the NFL and give our reactions to everything we witnessed. Are the Cardinals a contender? How do the Chiefs continue to squeak out wins? Who is the worst of the bottom feeders and will get the first pick of the draft? We also discuss what will be the biggest conundrum the CFP committee will have when picking the 12 best teams for the College Football Playoff. We also talk a little Heisman to see where we are at after some big upsets occurred this weekend.

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Shoulda Bet More with Will Hill - Ep. 129- Jonathan Von Tobel

Bill@vsin.com (GoldBoys.com) — Fri, 8 Nov 2024 11:00:00 +0000

We witnessed what might have been the game of the year in the NFL. Will recaps and reacts to last night's Ravens win over the Bengals and what it means going forward. We've also brought Jonathan Von Tobel (@meJVT) of VSiN Primetime back to the pod! We talk to him about takeaways from the NBA only two weeks into the season. Which teams are proving to be legit? Which players should we be looking to to bet on season awards? We also go into this weekend in NFL as we go over our favorite bets of the weekend that you should take. We also talk some College Football as we are getting closer to the end of the season. Will the CFP committee have to make any tough decisions down the stretch? We also give out our favorite college football plays for the weekend as well.

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Shoulda Bet More with Will Hill - Ep. 128 - "The Bear" Chris Fallica

Bill@vsin.com (GoldBoys.com) — Wed, 6 Nov 2024 11:00:00 +0000

On today's episode, we've brought back "The Bear" Chris Fallica (@chrisfallica) from Fox Sports to the pod so we can take a view at the state of the NFL at the trade deadline. We take a look at the playoff picture of the AFC and the NFC as we try to determine which teams will stay in, fall out, and grab those elusive wild card spots. We discuss which team we favor in a hypothetical Super Bowl of the current 1 seeds, the Lions and the Chiefs. We give our thoughts on the MVP, Coach of the Year, and Offensive Player of the Year races. We also take a look into this weekend in College Football. As we get closer to the College Football Playoff, do we think there could be any surprises that squeeze into the field? We'll also give you our early leans for this weekend in College Football and The Bear has a special soccer pick he likes this week to give out!

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Shoulda Bet More with Will Hill - Ep. 127 - Kiev O'Neil

Bill@vsin.com (GoldBoys.com) — Mon, 4 Nov 2024 11:00:00 +0000

On today's episode, we've brought back Kiev O'Neil (@OBKiev) of The Odds Breakers not only to talk about this weekend in football, but to preview the upcoming College Basketball season! With the season beginning today, we discuss the way to find the edge in betting for tonight and beyond for the rest of the season. We also go over the teams we think will be competing to win the National Championship in April. We also give our reactions to this weekend in NFL and give our Monday Night Football betting preview for the Buccaneers and Chiefs. We also begin to look forward to this weekend in College Football and give some early plays that we like for Saturday.

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Shoulda Bet More with Will Hill - Ep. 126 - Sammy P

Bill@vsin.com (GoldBoys.com) — Fri, 1 Nov 2024 10:00:00 +0000

The World Series is now in the books with the Los Angeles Dodgers beating the New York Yankees in 5 games. Will recaps the wild 5th inning in game 5 and gives the Dodgers their props and the Yankees their postmortem. We also bring on from the Chicken Dinner podcast, Bet QL, and Fox Sports, Sammy P (@spshoot) to talk about this weekend in football. Sammy P gives us his best bets for this weekend in Week 9 NFL and we go over the huge matchup between Ohio St. and Penn St. that will have playoff implications. We also look at the state of the NFL MVP race halfway through the season to see which player's price is worth betting on.

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Shoulda Bet More with Will Hill - Ep. 125 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Wed, 30 Oct 2024 10:00:00 +0000

Join host Will Hill and Returning Guest Jeff Parles as they dive deep into the exciting world of sports betting on this week’s episode of "Shoulda Bet More." Tune in as they break down Game Five of the World Series, sharing insights and predictions that will keep you on the edge of your seat. But that’s not all—Will and Jeff will also tackle Thursday Night Football, offering their takes on matchups, player performances, and strategies. Whether you’re a seasoned bettor or just looking to get in on the action, this podcast is your go-to source for analysis, tips, and a bit of fun. Don’t miss out—after all, you shoulda bet more!

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Shoulda Bet More with Will Hill - Ep. 124 - Scott Seidenberg

Bill@vsin.com (GoldBoys.com) — Mon, 28 Oct 2024 10:00:00 +0000

We had a wild sports-filled weekend, and to give a recap and reaction, we've brought Scott Seidenberg (@ScottsOnAir) from VSiN and Pregame.com back to the podcast! Will and Scott give their takeaways from NFL week 8. Can Jameis Winston turn the Browns around? After an atrocious loss against the lowly Patriots, what can the Jets do to salvage their season? We also get a preview of tonight's MNF game between the Giants and the Steelers. We also do a deep dive into the World Series, recap and reactions from both Will and Scott on how it's gone so horribly wrong for the Yankees. What do the Yankees need to do to get the series at the very least, back to Los Angeles. We also talk about what you should be betting on for game 3 tonight.

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Shoulda Bet More with Will Hill - Ep. 123 - Tommy Lorenzo

Bill@vsin.com (GoldBoys.com) — Fri, 25 Oct 2024 10:00:00 +0000

The World Series begins tonight and we have the bets and analysis you need for tonight's game 1 between the New York Yankees and the Los Angeles Dodgers and for the series as a whole. To counter Will's Yankees fandom, we've brought on LA native, from the Cover the Weekend Podcast, Tommy Lorenzo (@sportsbooktom)! Will and Tommy discuss each teams strengths and weakness, how they matchup against each other, their favorite bets for the game tonight, their looks for World Series MVP, and their prediction on who wins the World Series and in how many games. Plus, we also get betting looks for this weekend in College Football and the NFL. Finally, we recap yesterday's Thursday Night Football game and how the referees could have missed an obvious facemask.

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Shoulda Bet More with Will Hill - Ep. 122 - Chris Macero

Bill@vsin.com (GoldBoys.com) — Wed, 23 Oct 2024 10:00:00 +0000

On this midweek episode of Shoulda Bet More, we invite back professional sports bettor and VSiN contributor, Chris Macero (@RealGadge) to the podcast! We get you ready for the TNF Vikings vs. Rams game, the start of the NBA regular season, and the World Series. Chris and Will give you some of their best bets for week 8 in the NFL and week 9 in College Football. Chris also gives us a season long bet in the NBA that he loves and a team he thinks can surprise this season. We also give a preview at what we may see in the World Series and give you our predictions on if the Dodgers or Yankees will take home the Commissioner's Trophy.

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Shoulda Bet More with Will Hill - Ep. 121 - Dave Ross

Bill@vsin.com (GoldBoys.com) — Mon, 21 Oct 2024 10:00:00 +0000

Join host Will Hill in a lively discussion with sports enthusiast Dave Ross on Shoulda Bet More. In this episode, they dive into the thrilling Mets vs. Dodgers Game 6 showdown, dissecting key moments. They also gaze into the future of MLB, speculating on the upcoming World Series and its potential. Plus, don't miss their insights on the latest NFL updates and predictions. Whether you're a die-hard sports fan or just love a good debate, tune in for expert analysis and engaging banter.

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Shoulda Bet More with Will Hill - Ep. 120 - Matt Youmans

Bill@vsin.com (GoldBoys.com) — Fri, 18 Oct 2024 10:00:00 +0000

We've got your football bets for the weekend as we've invited back Matt Youmans (@mattyoumans247) of VSiN to talk all things football. We've got Matt's best bets for Week 8 in College and Week 7 in the NFL. We go over the major games such as Georgia vs. Texas, Vikings vs. Lions, Chiefs vs. 49ers, and more! We talk which teams are the best in the NFL and College Football, and Matt talk about what has been the ref show in the NFL. Will also recaps a wild game 3 in the ALCS, the Dodgers taking a commanding 3-1 lead in the NLCS, and what he thinks the best bets are this weekend and whether or not we even see the Championship Series continuing through next week.

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Shoulda Bet More with Will Hill - Ep. 119 - Reed Wallach

Bill@vsin.com (GoldBoys.com) — Wed, 16 Oct 2024 10:00:00 +0000

On this midweek episode of Shoulda Bet More, we invite Reed Wallach (@ReedWallach) of The Early Reed Podcast and Sports Illustrated back to the podcast to talk some College Football and his New York Mets! Reed gives us some of his best bets for Week 8 of CFB. From Georgia/Texas and Alabama/Tennessee, to matchups not in the power conferences, we've got the bets you need. We also dive into the Heisman conversation as we approach the midpoint of the season. Are there any sneaky bets that can be made? Finally, we recap the NL/ALCS so far and talk about if the Guardians can get back into their series and can the Mets take control of the NLCS? Plus, reactions to some blockbuster trades in the NFL and the benching of Justin Fields in PIttsburgh!

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Shoulda Bet More with Will Hill - Ep. 118 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Mon, 14 Oct 2024 10:00:00 +0000

Join us in this episode of Shoulda Bet More as we dive into the latest MLB standings and break down the thrilling world of Monday Night Football predictions with our special guest, Jeff Parles. Tune in as we explore team performances, key matchups, and betting insights that could give you the edge in your next wager. Whether you're a seasoned bettor or just a sports fan, this episode is packed with analysis, hot takes, and the excitement of the game. Don’t miss out—let’s make those bets count!

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Shoulda Bet More with Will Hill - Ep. 117 - Brad Powers

Bill@vsin.com (GoldBoys.com) — Fri, 11 Oct 2024 10:00:00 +0000

This is gonna be a big weekend. Baseball's Championship Series begins, we get a great NFL slate, and we get a powerhouse College Football Saturday with marquee matchups. To give his analysis and bets on those games, we've brought Brad Powers (@BradPowers7) of the Bet The Board Podcast back to the podcast! We get his opinion on Texas/Oklahoma, Penn St./USC, and Ohio St./Oregon as well as some other games that are flying under the radar, but are great spots to make some bets. Will also goes over his NFL bets for the weekend and where we are at in the MLB Postseason and where we might end up at in the World Series.

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Shoulda Bet More with Will Hill - Ep. 116 - Dave Ross

Bill@vsin.com (GoldBoys.com) — Wed, 9 Oct 2024 10:00:00 +0000

We have been treated to four tight and extremely competitive Division Series matchups and to go over them, we've invited back Dave Ross (@drosssports) from Sunday Bet Prep on VSiN! We discuss how his Mets have come from rock bottom all the way to within one game of the NLCS. Are the Padres going to be able to finish the job against the Dodgers? Should the Yankees be worried with how their series is going with Aaron Judge seemingly missing? With Detroit's 9th inning blast to give them the win Monday, do they actually have a chance at upsetting Cleveland? Plus we go over the huge news of the Jets firing Robert Saleh. What does this mean for the Jets moving forward, will they be able to salvage their season? Finally, we get an early look at some Week 6 bets!

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Shoulda Bet More with Will Hill - Ep. 115 - Gill Alexander

Bill@vsin.com (GoldBoys.com) — Mon, 7 Oct 2024 10:00:00 +0000

What a wild sports weekend. So many College Football upsets, some wild NFL games, and some intense baseball series. To break it all down with an eye on what to take advantage of betting wise, we've invited back Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod!" We recap week 5 in the NFL and provide our takeaways. Are the Vikings a championship contender? Will Cleveland be picking first overall? We talk about some of the wild MLB postseason games that have been happening in the AL/NLDS and discuss if some of the best series lines to take at this point. Plus, we touch on what College Football will look like after this upset-filled weekend!

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Shoulda Bet More with Will Hill - Ep. 114 - Mitch Moss

Bill@vsin.com (GoldBoys.com) — Fri, 4 Oct 2024 10:00:00 +0000

The Division Series round is all set as we head into the weekend and to preview that round, we've invited from "Follow the Money" on VSiN, Mitch Moss (@MitchMossRadio) back to the pod! We break down the series' and the betting angles we like from them. Should the Orioles postseason performances of the past 2 years get Brandon Hyde fired? Does the Wild Card round change our opinion of any of these teams? We also go over this weekend of College and NFL football and give you our best bets from each so you can ahead on the books!

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Shoulda Bet More with Will Hill - Ep. 113 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Wed, 2 Oct 2024 10:00:00 +0000

Join host Will Hill in this episode of "Shoulda Bet More" as he sits down with passionate Mets fan Jeff Parles (@jeffparles) to dive into the excitement of the first day of the 2024 MLB playoffs. They’ll break down the day's thrilling matchups, share their predictions for what’s next, and explore what the future holds for their favorite teams. Whether you’re a die-hard baseball fan or just looking to get in on the playoff action, tune in for insights, hot takes, and a bit of banter that only true fans can appreciate. Don’t miss out on the fun—let’s talk playoffs!

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Shoulda Bet More with Will Hill - Ep. 112 - MLB Postseason Preview with NicLarson

Bill@vsin.com (GoldBoys.com) — Tue, 1 Oct 2024 10:00:00 +0000

After an exciting final day of baseball, it's finally here, the MLB Postseason! We've brought NicLarson (@NicLarsonGB) from the Goldboys discord onto the show to give you all the edge you need on betting this postseason. We recap the wild doubleheader that was Mets vs. Braves and discuss if the quick turnaround for each team will affect them in the Wild Card round. We go over each series and give you our best betting angles and predictions for how each series will go. We also go over full postseason bets, our World Series bets, and some lesser known bets that you can find the edge on by tuning in!

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Shoulda Bet More with Will Hill - Ep. 111 - Kiev O'Neil

Bill@vsin.com (GoldBoys.com) — Mon, 30 Sep 2024 10:00:00 +0000

It was a busy week 4 in the NFL on Sunday and we have the recaps and reactions from Will and Kiev O'Neil (@OBKiev) of The Odds Breakers! Are the Jets truly a contender after their upset loss to the Broncos at home? The Vikings continue to impress as they come away with a win at Green Bay, are they truly a title contender? Who is going to be the Rookie of the Year, Jayden Daniels or Malik Nabers? We look ahead to week 5 based on the early lines and give out our early leans. We also discuss some college ball reactions from this weekend and give you our early bets for week 6 on Saturday. Plus, the double header to decide the final NL Wild Card spots happens today, Will gives the scenarios and what he think will happen. Look for a preview show on Tuesday for the MLB Postseason as we give you our best bets on how we think these series will go.

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Shoulda Bet More with Will Hill - Ep. 110 - Chris Macero

Bill@vsin.com (GoldBoys.com) — Fri, 27 Sep 2024 10:00:00 +0000

We have a big weekend coming up, it's the final weekend of the MLB Regular Season. We are at the end of these division and wild card races and we've brought professional sports bettor and VSiN contributor, Chris Macero (@RealGadge), onto the pod to give us his analysis and betting perspective of the Postseason. We preview the final weekend of the season and give our final predictions on which teams will nab those final wild card spots. Chris gives insight on how he handicaps the Postseason and what he looks for in a World Series competing team. We give analysis on some of the biggest competitors and whether or not they can win the World Series, and Chris gives out some of his World Series exacta bets! Plus, Chris gives us his best bets for this weekend in College Football and the NFL and details why the Washington Commanders could be a very sneaky team the rest of the way this season. Plus, Will gives us his best bets for week 4 in the NFL and also gives us a rant on how the WNBA has fumbled with Caitlyn Clark.

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Shoulda Bet More with Will Hill - Ep. 109 - Stuckey

Bill@vsin.com (GoldBoys.com) — Wed, 25 Sep 2024 10:00:00 +0000

On this midweek episode of Shoulda Bet More, Stucky (@Stuckey2) from Action Network returns to the podcast to talk some football! We recap both games from Monday night. After 0-3 starts, is the season over for the Bengals and the Jaguars? Which of them, if either, still stand a chance at making the playoffs? How have the Minnesota Vikings started out the season on fire with Sam Darnold? We talk about Thursday night's matchup between the Cowboys and the Giants and give you our favorite leans and bets. Plus, a preview at Saturday's huge Georgia vs. Alabama game!

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Shoulda Bet More with Will Hill - Ep. 108 - Scott Seidenberg

Bill@vsin.com (GoldBoys.com) — Mon, 23 Sep 2024 10:00:00 +0000

Join us as we get the instant reaction to Sunday's week 3 slate with Scott Seidenberg (@ScottsOnAir) from Pregame.com! After a narrow victory against the Saints, does the seat get a little cooler for Eagles HC, Nick Siriani? The Seahawks, Steelers, and Vikings are all 3-0; are they actually for real? Is the Bryce Young era truly over after the Panthers get a big win with Andy Dalton? We also go over Kyle Shanahan's major call to attempt to kick a field goal that ended up costing them the game against the Rams. We look forward to two Monday Night Football games and give you our best bets on them. Plus, we look to baseball in the final week to try to determine who will be in and out in the wild card race!

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Shoulda Bet More with Will Hill - Ep. 107 - Femi Abebefe

Bill@vsin.com (GoldBoys.com) — Fri, 20 Sep 2024 10:00:00 +0000

We have a jampacked football weekend coming up and to get you ready, we've brought back from BetQL, Femi Abebefe (@FemiAbebefe)! Femi gives us the NFL teams he thinks are contenders and pretenders, which of the 0-2 teams will be able to recover, and his betting preview for week 3! We also get a look at potential NFL awards as well as where we are at for MLB awards with just over one week to go! Femi also gives us his favorite College Football bets this weekend. Plus, Will gives his week 3 plays and a quick postseason race recap as the MLB season winds down.

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Shoulda Bet More with Will Hill - Ep. 106 - Iain MacMillan

Bill@vsin.com (GoldBoys.com) — Wed, 18 Sep 2024 10:00:00 +0000

On this episode of Shoulda Bet More, we invite from Sports Illustrated and noted Falcons fan, Iain MacMillan (@IainMacBets) back to the podcast! We recap and reacted to the wild ending between the Falcons and the Eagles from Monday night. We do a lookahead to Thursday Night Football and the rest of Week 3 as we give you our best bets. Bryce Young has been benched by the Panthers, what do they do with him next and is their season outlook any better than it was before? Iain tells us who he believes are the contenders and pretenders of the NFL after week 2. Plus, since when has the "E" in ESPN stood for Eagles? Was bringing Jason Kelce on a good idea?

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Shoulda Bet More with Will Hill - Ep. 105 - Doug Kazirian

Bill@vsin.com (GoldBoys.com) — Mon, 16 Sep 2024 10:00:00 +0000

Week 2 is in the books and we've brought Doug Kezirian (@DougKezirian) onto the pod where him and Will give you their reactions to everything we saw this weekend. After 2 weeks, which teams are better or worse than we originally thought? After the number of upsets this weekend, can we still take advantage of the books as they lag behind? Who is it worth betting on for the first coach to be fired? Plus, a week 3 lookahead and Will gives his Monday Night Football best bet between the Falcons and the Eagles.

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Shoulda Bet More with Will Hill - Ep. 104 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Fri, 13 Sep 2024 10:00:00 +0000

On today's episode, we get you ready for Week 3 in College Football and Week 2 in the NFL. We've brought back one of our favorites, from Sports by the Book, Jeff Parles (@jeffparles)! Jeff gives his overreactions from Week 1 in the NFL. The guys discuss if the Cincinnati Bengals should be concerned going forward. They also give their best bets for this weekend in the NFL and College Football. Plus, Jeff and Will talk about who they think will be in and out of the postseason at the end of the MLB season in just a few weeks!

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Shoulda Bet More with Will Hill - Ep. 103 - Jason Weingarten

Bill@vsin.com (GoldBoys.com) — Wed, 11 Sep 2024 10:00:00 +0000

Now that week 1 is officially in the books, we can turn our attention a bit back to baseball. Jason Weingarten (@Spreadapedia) from VSiN returns to the pod to talk about the close division races and wild card races. With 3 weeks to go, which teams do Jason think end up making the postseason? Do the Yankees or Orioles take the AL East? Will the Braves be on the outside looking in? We also talk awards with Jason. We look at the odds compared to what they were at the start of the year, and are there still bets worth making for a possible upset? Jason also gives us his week 1 takeaways and early looks at week 2 plays. We also talk about Colorado and whether the Deion experiment will last.

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Shoulda Bet More with Will Hill - Ep. 102 - Matkafee

Bill@vsin.com (GoldBoys.com) — Mon, 9 Sep 2024 10:00:00 +0000

Welcome to Shoulda Bet More, the podcast where host Will Hill and special guest @matkafee dive deep into the upcoming NFL action. In this episode, Will and Matkafee break down the first weekend of the season, sharing insider insights, game predictions, and betting tips to help you make the most informed picks. Whether you're a seasoned bettor or just a football fan eager for a sneak peek, tune in to get the edge you need before kickoff!

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Shoulda Bet More with Will Hill - Ep. 101 - Adam Kaufman

Bill@vsin.com (GoldBoys.com) — Fri, 6 Sep 2024 10:00:00 +0000

What a way to open the NFL Regular Season, but we aren't done because we have a special Friday night game in Brazil! The Packers play the Eagles in São Paulo and to get the best bets for it, we've brought Adam Kaufman (@AdamMKaufman) from WKRO 680 and iHeartRadio Boston back to the pod! We do a quick preview of the game and give our best bets for it. We also preview the rest of Sunday's slate of games for week 1. Adam was high on the Patriots the last time we spoke, does he still feel optimistic about the direction of the team? We also get Adam's Super Bowl matchup and winners. Plus, Will recaps and reacts to the wild Ravens vs. Chiefs game and what it means for both teams moving forward. Also, Will previews week 2 of college football and gives his favorite bets of the weekend.

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Shoulda Bet More with Will Hill - Ep. 100 - Sammy P

Bill@vsin.com (GoldBoys.com) — Wed, 4 Sep 2024 10:00:00 +0000

We've made it to 100! Thanks to everyone that has tuned into the pod, we are glad you are enjoying it. More importantly, the NFL Regular Season begins tomorrow! To dive into the upcoming season and more specifically, Thursday's game between the Ravens and Chiefs, we've brought from the Chicken Dinner podcast, Bet QL, and Fox Sports, Sammy P (@spshoot)! We get his hottest take for the season, his favorite longshot awards plays, his and Will's best bets for Thursday's game as well as Sunday's games! Plus, we get the biggest takeaways from week 1 in College Football and some bets to look forward to on Saturday for week 2! You'll get your football fix on this episode, we promise.

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Shoulda Bet More with Will Hill - Ep. 99 - FranchiseKF

Bill@vsin.com (GoldBoys.com) — Fri, 30 Aug 2024 10:00:00 +0000

Tomorrow, we finally get the first full slate of College Football. It's week 1 time! We've invited College Football handicapper FranchiseKF (@FranchiseKF) to give us all the info we need as we truly kick off the season. We talk about what we witnessed in week 0 and discuss some takeaways. We also go over some of the biggest games and give you the best bets for this weekend so you can start adding to your bankroll. FranchiseKF also has sleeper picks to make the Playoff as well as to win the Heisman to get in now before the odds begin to lower! Plus, Will talks the MLB postseason races as we enter the final month of the season!

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Shoulda Bet More with Will Hill - Ep. 98 - Mike Sando

Bill@vsin.com (GoldBoys.com) — Wed, 28 Aug 2024 10:00:00 +0000

We are just one week away from the start of the NFL Regular Season! That also means that Mike Sando (@SandoNFL) of The Athletic has released his yearly QB Tiers list! We've invited Mike back onto the pod to talk the list as voted on by NFL coaches and executives so we can discuss how everything shook out. We discuss who rose and fell in the rankings and which players' rankings surprised us. Also, what do some QBs need to do heading into the year to improve their perception around the league. Plus, Mike also gives us the teams he thinks will be big sleepers this year!

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Shoulda Bet More with Will Hill - Ep. 97 - Joey Isaks

Bill@vsin.com (GoldBoys.com) — Mon, 26 Aug 2024 10:00:00 +0000

The US Open tennis tournament begins this week, so to help you get ready to hit some tennis bets for the next two weeks we've invited professional bettor, Joey Isaks (@joeyisaks) onto the pod! We discuss the favorites, the longshots, the first round matchups, and Joey gives us his favorite bets to win it all in the men's bracket as well as the women's bracket! Joey also gives us his tips when trying to do courtside betting at the matches. Tune in to get a jump start to your bankroll for one of the biggest tennis tournaments of the year!

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Shoulda Bet More with Will Hill - Ep. 96 - Ian Eagle

Bill@vsin.com (GoldBoys.com) — Fri, 23 Aug 2024 10:00:00 +0000

As we head into the final weekend of the NFL preseason, we wanted to get a perspective of the game from someone who calls it, so we've invited back Ian Eagle! The NFL on CBS play-by-play man gives us insight into how he prepares to call a game, and how it allows him to analyze the league differently than most other tv analysts. As a New York guy, we get his insight into how the Jets and Giants offseason have gone and where they can go this upcoming season. Since announcing is the family business, we talk about his son Noah Eagle working play-by-play for Olympic Basketball. It's also never too early to start talking NBA basketball and as Ian also does work with TNT and the YES Network for the Nets, we discuss what the Nets have done this offseason and how it might affect their future!

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Shoulda Bet More with Will Hill - Ep. 95 - John Laghezza

Bill@vsin.com (GoldBoys.com) — Wed, 21 Aug 2024 13:00:00 +0000

We are getting so close to the final month of the MLB season! We thought do to a check in on where we are at as we prepare for the postseason, so we've brought from The Athletic, John Laghezza (@JohnLaghezza)! We talk about which teams are making the postseason and who will claim the last wild card spots as the race is coming down to the wire. John gives us his state of the game opinions such as pace of play changes, umpiring calls, and more! John also gives us his takes on the overrated and underrated teams heading into the upcoming NFL season. Plus, Will previews week 0 of College Football on Saturday. Tune in to get the best bets for this upcoming weekend and beyond!

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Shoulda Bet More with Will Hill - Ep. 94 - "The Bear" Chris Fallica

Bill@vsin.com (GoldBoys.com) — Mon, 19 Aug 2024 10:00:00 +0000

Welcome to Shoulda Bet More, the podcast where sports betting meets sharp analysis and lively conversation. Hosted by Will Hill, a seasoned expert in the world of wagers, this show dives deep into the latest action across the NFL, MLB, College Football, and occasionally, even tennis.

In this episode, Will is joined by Chris Fallica, renowned sports analyst from Fox Sports. He's back!! Together, they break down the latest games, uncover betting trends, and offer their predictions for the weeks ahead. Whether you're a seasoned bettor or just curious about the odds, Shoulda bet more delivers the information and entertainment you need to up your game.

Tune in for a mix of expert advice, engaging banter, and all the insights you need to make informed bets. Don’t miss out—listen now and find out why you shoulda bet more!

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Shoulda Bet More with Will Hill - Ep. 93 - Scott Seidenberg

Bill@vsin.com (GoldBoys.com) — Fri, 16 Aug 2024 10:00:00 +0000

Join Will Hill and Scott Seidenberg (@ScottsOnAir) as they dive into the high-stakes drama of MLB pennant races and break down the latest buzz from NFL training camps. Get the inside scoop on what’s really happening in the sports world and discover where you shoulda bet more! 🎙️🏆🏈

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Shoulda Bet More with Will Hill - Ep. 92 - Gill Alexander

Bill@vsin.com (GoldBoys.com) — Wed, 14 Aug 2024 10:00:00 +0000

On today's pod, we've asked Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" to return to give his looks for the upcoming NFL season. He supplies us with his hot takes and previews some of his favorite teams as well as teams he thinks could have wildly differing outcomes for this upcoming season. We also talk baseball as we head into the final month and a half of the season. How are the awards looking and which of the teams that are competing for a playoff spot the biggest threats to win the World Series? We also get a quick US Open tennis preview!

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Shoulda Bet More with Will Hill - Ep. 91 - Mitch Moss

Bill@vsin.com (GoldBoys.com) — Mon, 12 Aug 2024 10:00:00 +0000

Week 1 of the NFL Preseason is in the books and we've brought back from "Follow the Money" on VSiN, Mitch Moss (@MitchMossRadio) to talk about some of his season long NFL bets! We also discuss MLB division races, Cy Young awards, Rookie of the Year Awards, and MVP awards for the AL and the NL. Also talked about is the way to bet baseball with a different postseason in the past, are longshots more viable than ever? Plus, Will recaps a crazy ending to the gold medal game in Olympic basketball and gives some bets for upcoming MLB games.

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Shoulda Bet More with Will Hill - Ep. 90 - Matt Youmans

Bill@vsin.com (GoldBoys.com) — Fri, 9 Aug 2024 10:00:00 +0000

On today's episode, we invite Matt Youmans (@mattyoumans247) from VSiN onto the pod to talk some MLB Postseason races and some football! We get Matt's take on which teams will win each division and the ones who will take up the wild card spots. Could the Braves possibly miss the postseason altogether? Matt gives us some Over/Under wins plays that are worth a look for NFL and College Football! We also get a preview at Matt's famed top 50 fast food power rankings. Plus, Will has a play worth taking for the Olympic basketball final between the US and France!

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Shoulda Bet More with Will Hill - Ep. 89 - Steve Fezzik

Bill@vsin.com (GoldBoys.com) — Wed, 7 Aug 2024 10:00:00 +0000

The first week of the NFL Preseason begins tomorrow, and to get the edge on preseason betting, we've invited Steve Fezzik (@FezzikSports) from Pregame.com back to the pod! Steve gives us his approach to preseason betting and how he reads shifting lines and bets to his advantage. We also get his opinion on how the new kickoff will affect over/under betting. We discuss if it's right that the NFL is ending games in the preseason early when games are being bet on through their gaming partners. We also talk the new surcharge that DraftKings is implementing in some states and how it reminds Steve of another product that had to be walked back on. Tune in for the most informative content you'll get for the NFL Preseason!

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Shoulda Bet More with Will Hill - Ep. 88 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Mon, 5 Aug 2024 10:00:00 +0000

He's back! To discuss what has suddenly become some very competitive MLB division races, Jeff Parles (@jeffparles) returns to the pod! We talk about how the Phillies and Dodgers have let the teams below them slowly creep up to first place, so which team is more likely to blow the division? We get Jeff's opinion on the AL East race between the Yankees and the Orioles with the trade deadline wrapped up. We also discuss which teams are going to get those last wild card spots in the AL and NL. Plus, Jeff gives us some of his new NFL takes and an excellent analysis on the knockout round in Olympic Basketball.

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Shoulda Bet More with Will Hill - Ep. 87 - John Jastremski

Bill@vsin.com (GoldBoys.com) — Fri, 2 Aug 2024 10:00:00 +0000

Now that we've had time to digest what's happened at the trade deadline, we've brought on from SNY and the "New York, New York" podcast on the Ringer, John Jastremski (@john_jastremski)! We go over what the Yankees and Mets did at the deadline and was it enough for either team? We look at the rest of the league and try to predict the division races from here on out as well as which teams will take the wild card spots? Plus, John also gives us some of his NFL opinions on which teams are overvalued/undervalued?

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Shoulda Bet More with Will Hill - Ep. 86 - Hitman

Bill@vsin.com (GoldBoys.com) — Wed, 31 Jul 2024 10:00:00 +0000

Dive into the latest edition of "Shoulda Bet More" as we sit down with Hitman from TheHammerHQ! 🏈💰 Get ready for a thrilling discussion packed with insider knowledge and expert predictions on the NFL preseason. Whether you’re a seasoned bettor or just starting out, Hitman’s insights are a game-changer.

All this action is brought to you by the Gold Boys Network. Don’t miss out—hit that play button and level up your betting game! 🔥🏆

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Shoulda Bet More with Will Hill - Ep. 85 - Brad Thomas

Bill@vsin.com (GoldBoys.com) — Mon, 29 Jul 2024 10:00:00 +0000

We continue our series of College Football and NFL previews with Brad Thomas (@MrBradThomas) from NBC Sports and GoldBoys! Brad gives us his overrated and underrated teams in both College Football and the NFL. As an SEC guy, Brad gives us his takes on Alabama, Ole Miss, and Texas in their first year in the SEC. Also as an extra bonus, we get tips on betting the Olympics! Plus, Will goes over some of the trades that have been made in baseball as we head towards the trade deadline!

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Shoulda Bet More with Will Hill - Ep. 84 - Aaron Schatz

Bill@vsin.com (GoldBoys.com) — Fri, 26 Jul 2024 10:00:00 +0000

We are less than a week from the Hall of Fame game in Canton to kickoff the NFL Preseason. To get another perspective of how the season will turn out, we've brought back the father of DVOA, Aaron Schatz of FTN Fantasy. Aaron lets us in on what the advanced stats for the upcoming season say about what various teams' strengths and weaknesses are, where teams will place in their divisions, and how their projections compare to the wins market so you can make a bet on a team's over/under win total! Plus, with the Yankees struggling heading into a pivotal series with the Red Sox in Boston, Will goes scorched earth on the Yankees organization. You aren't gonna want to miss this...

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Shoulda Bet More with Will Hill - Ep. 83 - Femi Abebefe

Bill@vsin.com (GoldBoys.com) — Wed, 24 Jul 2024 10:00:00 +0000

We have the awards guru from VSiN, Femi Abebefe (@FemiAbebefe) on today's episode of Shoulda Bet More! In baseball, we talk about the race for the AL MVP, AL/NL Cy Young, and Femi gives us a World Series exacta that he loves the value in! In football, we get his takes on who will end up being the worst team in the league, and who will surprise which may trigger a coach of the year bet. We also get a longshot award for a rookie that Femi sees a lot to love in. Plus, Will lets us in on an NFL future that intrigues him. Tune in for that and more on today's episode!

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Shoulda Bet More with Will Hill - Ep. 82 - Geoff Schwartz

Bill@vsin.com (GoldBoys.com) — Mon, 22 Jul 2024 10:00:00 +0000

We can almost say football is back! NFL Teams report to training camps this week and to talk about his experience and his opinions on the upcoming season, we've brought on former NFL Offensive Lineman and from Fox Sports, Geoff Schwartz (@geoffschwartz)! Geoff discusses how he handicaps games based on offensive line play from what he knows from his playing days. We also get his opinions on teams he likes to go over and under their projected win totals. We get some awards discussion from him and he also gives us some of his favorite win total bets from the upcoming college football season as well! Tune in for what is a wildly entertaining and informative show!

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Shoulda Bet More with Will Hill - Ep. 81 - Adnan Virk

Bill@vsin.com (GoldBoys.com) — Fri, 19 Jul 2024 10:00:00 +0000

The second half of the MLB season begins today! For more preview of how the second half will play out, we've brought back Adnan Virk (@adnansvirk) from MLB Network and the Cinephile with Adnan Virk podcast! We talk about the AL East, is it a two team race between the Orioles and the Yankees, or can the Red Sox continue their hot streak and compete for the division? We discuss the trade deadline, who are the big names that will be moving and what teams will be looking to add to solidify a postseason run? Paul Skenes has had an unbelievable first half of the season, so can the rookie also win the Cy Young award? Plus, Adnan gives us some of his must see movies of the summer and into the fall!

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Shoulda Bet More with Will Hill - Ep. 80 - Dave Ross

Bill@vsin.com (GoldBoys.com) — Wed, 17 Jul 2024 10:00:00 +0000

With the All-Star Game now behind us, we look forward to the 2nd half of the MLB season. To get us started, we've invited Dave Ross (@drosssports) from Sunday Bet Prep on VSiN back to the podcast! When he was on last, his Mets were in the gutter. Now, they have brought themselves back to looking like a potential playoff team! We talk about what they will do at the upcoming trade deadline and whether or not betting on them to make the postseason is a good idea. We also talk about the state of the divisions and which first place teams at the half won't be there at the end of the season. We also go over a little NFL for the upcoming season. Plus, Dave gives us his favorite bets for The Open in Scotland this weekend as well as some underdog UFC picks!

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Shoulda Bet More with Will Hill - Ep. 79 - Kiev O'Neil

Bill@vsin.com (GoldBoys.com) — Mon, 15 Jul 2024 10:00:00 +0000

On this episode of Shoulda Bet More with Will Hill we dive deep with our special guest, Kiev O'Neil from The Odds Breakers (@OBKiev). He's back! and brings his sports-betting expertise to the table as we discuss the hottest topics in the gambling universe. Tune in as Kiev joins us for an engaging discussion on NFL schedules, the MLB All-Star break, and the thrill of college football. Get ready to break down the odds and make your predictions with the best in the business, right here on Shoulda Bet More podcast.

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Shoulda Bet More with Will Hill - Ep. 78 - Jonathan Von Tobel

Bill@vsin.com (GoldBoys.com) — Fri, 12 Jul 2024 10:00:00 +0000

One of our favorite guests, Jonathan Von Tobel (@meJVT) of VSiN Primetime returns to the pod! We discuss NBA Summer League and how to bet it. We talk about the upcoming NBA season and any pre-season award betting looks. As we are a little bit more than a month out of football season starting, we talk about overrated/underrated college football teams of the Big 12 and Mountain West conferences. We also discuss NFL football and JVT has a sneaky Offensive Player of the Year bet that he really likes. Tune in to find out!

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Shoulda Bet More with Will Hill - Ep. 77 - Julian Edlow

Bill@vsin.com (GoldBoys.com) — Wed, 10 Jul 2024 11:55:11 +0000

As we get deeper into the summer season, fall creeps ever closer. Which means football is coming up soon! To talk about all things football as well as NBA Summer League, and baseball, we've brought back Julian Edlow (@julianedlow) from the DraftKings Network! Julian gives us his NFL wins over/under takes and his thoughts on some player prop bets that he likes. We also get a College Football Week 1 betting preview from him. He also talks us through his betting strategy for Summer League as well as his thoughts about the upcoming NBA season! Plus, Will talks about which NFL team he really likes this season and what bets he likes for them.

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Shoulda Bet More with Will Hill - Ep. 76 - "The Bear" Chris Fallica

Bill@vsin.com (GoldBoys.com) — Mon, 8 Jul 2024 10:00:00 +0000

The Bronx is burning! The Yankees have been struggling for the past month and to talk about their struggles, we've brought back "The Bear" Chris Fallica (@chrisfallica) from Fox Sports! Will and Chris discuss how the Yankees have got to this point, whether or not they can hold on to a playoff spot, and what needs to be done for them to right the ship. They also talk about the upcoming college football season. Which teams Chris thinks are overrated and underrated, and who he thinks has sneaky potential to win the Heisman Award. Plus, Chris gives his takes and bets on the Euros and Copa America tournaments. Tune in to get the edge on the books!

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Shoulda Bet More with Will Hill - Ep. 75 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Fri, 5 Jul 2024 10:00:00 +0000

One of our favorite guests, from Sports by the Book, Jeff Parles (@jeffparles) is back! Will and Jeff talk about how Jeff's Mets is having a post Grimace-First-Pitch resurgence. Is it worth a bet on them to make the postseason with the run they've been making? On the other side of the city, the Yankees have struggled. What do they need to do to keep pace with the Orioles to try to win the AL East? What futures bets does Jeff like at this stage of the season? We also get Jeff's reaction to the NBA offseason and where he sees the upcoming NBA season going. We also talk the most intriguing NFL team this season and Jeff gives us his favorites to make the College Football Playoff in the first season of a 12 team playoff!

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Shoulda Bet More with Will Hill - Ep. 74 - Reed Wallach

Bill@vsin.com (GoldBoys.com) — Wed, 3 Jul 2024 10:00:00 +0000

On this episode of Shoulda Bet More, Reed Wallach (@ReedWallach) of The Early Reed Podcast and Sports Illustrated swings by to give his thoughts on NBA Free Agency and College Football! We discuss the Free Agency moves that have been made and which teams are best situated coming into the season to win the NBA Finals. With College Football coming up in a little over a month, we go over how teams will fare in their new conferences, overrated and underrated teams, and who the Playoff and National Championship threats are. Plus, Reed gives us a Heisman bet he likes coming into the season!

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Shoulda Bet More with Will Hill - Ep. 73 - Gill Alexander

Bill@vsin.com (GoldBoys.com) — Mon, 1 Jul 2024 10:00:00 +0000

July has begun which means it's time for Wimbledon. To talk some lawn tennis, we've brought back Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod." Gill gives us some of his analysis of the men's and women's tournament that lead to the bets he likes for the first round of the tournament all the way to the finals. Gill also gives us his football hot takes for the upcoming NFL season and how it may lead to a possible longshot playoff contender. Plus Will gives us a look at how NBA Free Agency is going.

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Shoulda Bet More with Will Hill - Ep. 72 - Brad Powers

Bill@vsin.com (GoldBoys.com) — Fri, 28 Jun 2024 10:00:00 +0000

As summer starts, football draws ever closer. On this episode of Shoulda Bet More, we've invited Brad Powers (@BradPowers7) of the Bet The Board Podcast onto the pod to give us his analysis on this upcoming season of College Football. In it we discuss the overrated and underrated teams of the upcoming season, over/under on win totals, Heisman Trophy bets, National Championship bets, week 0 and 1 bets, and College Football Playoff bets now that it has expanded to 12 teams. How will teams like Oregon and Texas do in the Big Ten and SEC respectively? Will Alabama be able to preform at the same level as in the Saban era with him now retired? Plus, Will recaps/analyzes the NBA Draft and the huge trade that went down between the Kicks and the Nets.

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Shoulda Bet More with Will Hill - Ep. 71 - Drew Dinsick

Bill@vsin.com (GoldBoys.com) — Wed, 26 Jun 2024 10:00:00 +0000

Now that we are officially in the NBA offseason, it's time for the NBA Draft. To give his analysis and predictions, we've invited Drew Dinsick (@whale_capper) of NBC Sports back onto the podcast. We get his thoughts on who the first 6 picks will be, what the Hawks should do with the number 1 pick, where Zach Edey will end up in the draft, and what he thinks will happen this offseason when it comes to big name free agents and trades. Plus, with the Olympics coming up, Drew gives his thoughts on how many golds USA Swimming can get in Paris, and how he goes about handicapping swimming. Also, we get his NFL hot takes on the upcoming season and how it's affecting one of the bets he's looking at for the Super Bowl. Tune in to the pod get the edge on the big name sports plus more!

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Shoulda Bet More with Will Hill - Ep. 70 - Alex B. Smith

Bill@vsin.com (GoldBoys.com) — Mon, 24 Jun 2024 10:00:00 +0000

The best two words in sports...Game Seven. Tonight, the Stanley Cup Winner is decided between the Edmonton Oilers and the Florida Panthers. To give the best insight on the game tonight, we've invited Alex B Smith (@axmithsports) of The Ice Guys to the pod to give his best bets and leans. We talk about how the series has gotten to this point as it looked like the Panthers were going to coast to a championship up three games to none. Even if the Oilers lose, is there anyway Connor McDavid doesn't win the Conn Smythe Award? Plus, O/U leans and finally, Will's and Alex's pick for who wins it all tonight. Get ready for an epic game seven by getting the biggest betting edge and tuning in!

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Shoulda Bet More with Will Hill - Ep. 69 - Adam Chernoff

Bill@vsin.com (GoldBoys.com) — Fri, 21 Jun 2024 10:00:00 +0000

Will is joined by Adam Chernoff (@adamchernoff) on this episode of the Shoulda Bet More podcast. The two touch briefly on the NHL Stanley Cup Finals before diving deep into the upcoming NFL season. Can the Oilers force a game seven against the Panthers. Adam shares some of his controversial takes for the upcoming season. Will the Carolina Panthers be a wildcard contender? Will Breece Hall win Offensive Player of the Year? Will the Broncos be the worst team in the league? Can the Chargers make the playoffs? Tune in to hear everything these two have to share!

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Shoulda Bet More with Will Hill - Ep. 68 - Jason Weingarten

Bill@vsin.com (GoldBoys.com) — Wed, 19 Jun 2024 10:00:00 +0000

We are nearing the end of June, so we've brought Jason Weingarten (@Spreadapedia) from VSiN back to the pod to talk some baseball. We get his takeaways on the division races and end of season awards such as league MVPs, Cy Youngs, and Rookies of the Year. Where those bets stand, who he likes, and who he's keeping an eye on who may not be a favorite right now! Plus, the Celtics have won the NBA Finals! Will gives a post-mortem on them and the NBA Playoffs as a whole. Also, Jason goes over some of his bad golf beats and how he's planning on righting the ship!

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Shoulda Bet More with Will Hill - Ep. 67 - Scott Seidenberg

Bill@vsin.com (GoldBoys.com) — Mon, 17 Jun 2024 10:00:00 +0000

Scott Seidenberg (@ScottsOnAir) from Pregame.com returns to the pod as we get his takes on the NBA Finals, Stanley Cup Finals, and on the MLB season! With both the NBA and the NHL's Finals mirroring each other, do we see both series get extended to a game 6? Will Jaylen Brown or Jason Tatum win Finals MVP if the Celtics close it out? Is there any chance Connor McDavid can win the Conn Smythe Award even if the Oilers lose? Who is the favorite to win the NL MVP now that Mookie Bets is out with a broken hand? Plus, trade talk for the teams who plan to be seriously competing for the World Series this year.

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Shoulda Bet More with Will Hill - Ep. 66 - Matt Grissom

Bill@vsin.com (GoldBoys.com) — Fri, 14 Jun 2024 10:00:00 +0000

We are down to 8 teams and the College World Series officially starts today! We've brought back from CollegeBaseballInsiders.com and VSiN, Matt Grissom (@GrissomOnX) to get an update on what we've seen so far in the tournament, and to get his thoughts and predictions on the 8 teams remaining! We get Matt's best bets on each matchup in the first round, plus who he thinks will come out of each bracket to meet in the finals. Also, with Boston up 3-0 in the NBA Finals, is there any chance that Dallas can avoid being swept? Get ready for a big weekend of betting by tuning in!

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Shoulda Bet More with Will Hill - Ep. 65 - Ben Wilson

Bill@vsin.com (GoldBoys.com) — Wed, 12 Jun 2024 10:00:00 +0000

As the NBA and Stanley Cup Finals keep going on, Ben Wilson (@Ben_Wilson_1) from ESPN+, FOX, and VSiN joins the podcast to give his perspective on how each series is going! Ben and Will discuss which team has a better chance of climbing out of their 0-2 deficit, the Mavericks or the Oilers. Ben and Will give their bets and predictions for how each series will end. They also talk about the upcoming NBA draft! Will the draft class being weak provide the ability to get good lines on where players end up going? Which teams look the best going into this weekend's College World Series? Find out all of that and more on today's episode!

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Shoulda Bet More with Will Hill - Ep. 64 - Jonathan Von Tobel

Bill@vsin.com (GoldBoys.com) — Mon, 10 Jun 2024 10:00:00 +0000

The Celtics have taken a commanding 2-0 lead in the NBA Finals. To discuss how the Celtics are doing it, we've brought Jonathan Von Tobel (@meJVT) of VSiN Primetime back to the pod! Will and JVT go over what the Celtics have done right, what the Mavericks have done wrong, and what the Mavericks can do to get back into this series. Jayson Tatum is currently the favorite to win Finals MVP, but is that truly the smart bet? Plus, some early NBA Futures for next season! Tune in to get the betting edge!

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Shoulda Bet More with Will Hill - Ep. 63 - Kelley Bydlon

Bill@vsin.com (GoldBoys.com) — Fri, 7 Jun 2024 10:00:00 +0000

Game 1 of the NBA Finals is in the books, and what a dominant win by the Boston Celtics. Kelley Bydlon (@KelleyBydlon) from VSiN's "A Numbers Game" joins Will as he returns to the pod to get an instant reaction to what we saw and what it means for the rest of the series. What does Dallas need to do to win in game 2. How does the outcome of game 1 change betting strategies moving forward in the series? Who is most likely to win Finals MVP? Also, it sounds as if Dan Hurley might leave UConn for the Lakers. What does it mean for UConn, LeBron, and the Lakers future?

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Shoulda Bet More with Will Hill - Ep. 62 - Jason McIntyre

Bill@vsin.com (GoldBoys.com) — Wed, 5 Jun 2024 10:00:00 +0000

Joining Will on this episode of Shoulda Bet More is Jason McIntyre (@jasonrmcintyre) from The Straight Fire podcast and The Herd! The two share what they're looking at as the NBA Finals approach. Should the Mavericks be the favorites to win it all? Should Angel Reese receive credit for the popularity of the WNBA or should all the credit go to Caitlin Clark? Does Tucupita Marcano deserve a lifetime ban from the MLB? Hear it all on this episode of Shoulda Bet More!

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Shoulda Bet More with Will Hill - Ep. 61 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Mon, 3 Jun 2024 10:00:00 +0000

Joining Will on the pod today is one of our favorite guests, from Sports by the Book, Jeff Parles (@jeffparles)! They talk about the takeaways from each division in baseball two months into the season. Who they think are making the postseason and who will be on the outside looking in. They also discuss who will win and who is worth betting on the Cy Young award for each league as well as the MVP award. They look forward to the NBA Finals and give a mini-preview on how they think the series will go. Jeff also goes through who he thinks will surprise this NFL season based on the schedule and teams' offseasons. Plus, will the WNBA do anything about trying to protect Caitlyn Clark after she got shoulder checked against the Chicago Sky?

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Shoulda Bet More with Will Hill - Ep. 60 - Matt Grissom

Bill@vsin.com (GoldBoys.com) — Fri, 31 May 2024 10:00:00 +0000

The NCAA Baseball Tournament begins this weekend! Three weekends of baseball culminating in the College World Series. To get you ready, we've invited, from CollegeBaseballInsiders.com and VSiN, Matt Grissom (@GrissomOnX)! Matt goes over everything you need to know to bet the tournament, his favorites from each regionals, and his favorite bet to win the tournament! Plus, the NBA Finals are set and it will be the Dallas Mavericks facing off against the Boston Celtics. Will give a mini lookahead to see where each team is at before he gives his picks next week!

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Shoulda Bet More with Will Hill - Ep. 59 - Adam Kaufman

Bill@vsin.com (GoldBoys.com) — Wed, 29 May 2024 10:00:00 +0000

With the Celtics sweeping the Pacers and reaching the NBA Finals, we thought to bring on Adam Kaufman (@AdamMKaufman) of WRKO 680 in Boston to give us a Boston perspective on sports and betting! Should Boston be concerned about having such an easy path to the Finals? How do they matchup against either the Mavericks or the Timberwolves? What is Adam's Finals prediction? Can the Patriots out-pace their projected win total? Will we see Drake Maye this season or is it Jacoby Brissett's team? How is the Red Sox's season up to this point? Will they surpass their win total? Plus, Will has a baseball future that he believes is the last chance to take! Tune in to find out and beat the books!

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Shoulda Bet More with Will Hill - Ep. 58 - Dave Ross

Bill@vsin.com (GoldBoys.com) — Mon, 27 May 2024 10:00:00 +0000

Happy Memorial Day! Will invites a new guest, the host of Sunday Bet Prep on VSiN, Dave Ross (@drosssports)! The guys talk everything from MLB, NFL, NBA, UFC, and the PGA Tour! They discuss some of their favorite picks in each sport and how they feel about the various teams and players. Plus, Will goes though some of the baseball games to watch on Memorial Day!

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Shoulda Bet More with Will Hill - Ep. 57 - Mitch Moss

Bill@vsin.com (GoldBoys.com) — Fri, 24 May 2024 10:00:00 +0000

It's Memorial Day weekend and to get you guys some great picks heading into the long weekend, Will has invited from "Follow the Money" on VSiN, Mitch Moss (@MitchMossRadio)! The guys talk a ton of baseball including which longshots can possibly sneak their way the Cy Young award in each league, the threat level of the division leaders and some of those in wild card slots, and longshots to win the World Series. Are the Timberwolves in any trouble after game one now that Dallas is favored in the series? How does Boston match up against either of these teams? We get Mitch's take on his bets for the NFL season now that he's seen the schedule. Plus, NHL bets: who wins the Stanley cup and who wins the Conn Smythe Award?

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Shoulda Bet More with Will Hill - Ep. 56 - Dustin Swedelson

Bill@vsin.com (GoldBoys.com) — Wed, 22 May 2024 10:00:00 +0000

Joining Will on the pod for this episode, from VSiN and the Double Play Podcast on the DraftKings Network, Dustin Swedelson! We are just about two months into the baseball season, so how do the guys think the rest of the season is going to shake out? We get their takes on some of the competing teams. Dustin also has some end of season awards bets and a World Series future he really likes. A preview on the Timberwolves/Mavericks series, a Knicks post-mortem and offseason lookahead, and one team that Dustin is going all-in on this upcoming NFL season. Tune in to find out!

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Shoulda Bet More with Will Hill - Ep. 55 - Gill Alexander

Bill@vsin.com (GoldBoys.com) — Mon, 20 May 2024 10:00:00 +0000

What. Just. Happened? Coming directly off the heels of the Nuggets blowing a 20 point lead against the Timberwolves in game 7, Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" returns to the podcast with Will to give their raw reactions to what we all just witnessed. They also talk about how the Pacers took care of the Kicks in MSG in that game 7. An early look at the upcoming Conference Finals series and some betting looks that intrigue the guys. We also get Gill's season long NFL bet that he's locking in after the schedule release. Plus a look at the bets teams in MLB this year and whether or not they can keep it up until October.

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Shoulda Bet More with Will Hill - Ep. 54 - Jonathan Von Tobel

Bill@vsin.com (GoldBoys.com) — Fri, 17 May 2024 10:00:00 +0000

One of our favorite guests, Jonathan Von Tobel (@meJVT) of VSiN Primetime returns to the pod to talk NBA Playoffs and NFL Futures after the release of the schedule! After the Timberwolves blew out the Nuggets in game 6, we get the best words in sports: game 7. Will and JVT talk about how we ended up here and who they feel will come out on top and why after what has been a crazy back and forth series. They also talk about whether or not the Knicks can close out their series on the road and what the best bet is for that game. Plus, futures bets that may be affected by how the schedule shook out for some teams. Tune in to get a leg up on the books!

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Shoulda Bet More with Will Hill - Ep. 53 - Brad Thomas

Bill@vsin.com (GoldBoys.com) — Wed, 15 May 2024 10:00:00 +0000

From NBC Sports and GoldBoys, Brad Thomas (@MrBradThomas) joins will to talk a number of sports on the pod. Will and Brad talk break down each NBA Playoffs series from an analytical and betting perspective, giving you some picks they like for individual games and each series as a whole. They also go over the upcoming PGA Championship, where Brad gives some of his favorite looks and why it might not be such a walk in the park for Scottie Scheffler. Plus, some NFL and College Football futures looks from Brad!

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Shoulda Bet More with Will Hill - Ep. 52 - Scott Seidenberg

Bill@vsin.com (GoldBoys.com) — Mon, 13 May 2024 10:00:00 +0000

From Pregame.com, Scott Seidenberg joins the podcast to talk all things NBA, NFL, NHL, and MLB with Will! How have the Nuggets got themselves back into this series with Minnesota and will they end up winning the series? Will Tom Thibodeau playing his players too long be the reason the Knicks potentially lose the series to the Pacers? Can the Cavaliers put up any fight against the Celtics? Who ends up advancing from the Mavericks/Thunder series? Scott gives his predictions for the rest of the Stanley Cup Playoffs and even gives out his favorite bet for the Conn Smythe award. Why does the media disrespect the New York Jets coming into this season? Finally, what do the Yankees need to take the AL East and the World Series this year. It's a jampacked episode, so tune in to get your sports and betting fix!

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Shoulda Bet More with Will Hill - Ep. 51 - Mike Sando

Bill@vsin.com (GoldBoys.com) — Fri, 10 May 2024 10:00:00 +0000

NFL Senior Writer for The Athletic, Mike Sando (@SandoNFL) returns to the podcast to chat NFL with Will! In it, they talk about which teams have had a good or bad offseason after we've had some time to process the draft. They also talk about the QB tier list and which QBs they expect to rise and fall in the upcoming season, and will the Chargers be immediately competitive with the hiring of Jim Harbaugh? Also, The Knicks win game 2, but can they win in Indiana with their mounting injuries? The Cavs upset the Celtics in game 1, what does that mean for the series moving forward? Plus, Will gives some of his best bet looks for today's games. Tune in to find out!

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Shoulda Bet More with Will Hill - Ep. 50 - NicLarson

Bill@vsin.com (GoldBoys.com) — Wed, 8 May 2024 10:00:00 +0000

On today's episode, NicLarson (@NicLarsonGB) from GoldBoys stops by to talk the ongoing NBA Playoffs and the MLB season so far. He talks about his day to day betting process and how he looks for the lines that he likes, looks for each league's Cy Young award at this point, and some stories about working in a AA clubhouse back in the day with some soon to be major leaguers. Also, can Denver fight their way out of a 0-2 hole on the road? Takeaways from a poorly officiated game 1 in the Knicks/Pacers series and a bonus review of the Roast of Tom Brady!

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Shoulda Bet More with Will Hill - Ep. 49 - Andy McCollough

Bill@vsin.com (GoldBoys.com) — Mon, 6 May 2024 10:00:00 +0000

On this episode of Shoulda Bet More, Andy McCollough, Senior Writer (@ByMcCullough) for The Athletic, comes onto the pod to talk about his new book, "The Last of His Kind," a biography of Clayton Kershaw. We get a little preview about some of the topics in the book such as talks about his regular season success vs. his postseason struggles and him and the Dodgers finally winning the World Series in 2020. Andy also gives some of his thoughts on the MVP race and who he thinks is built to win the World Series this year. Plus, Will goes over the final weekend of round 1 of the NBA Playoffs and the Timberwolves game 1 win against the Nuggets in round 2. Also some of the bets bets for the round 2 series coming up!

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Shoulda Bet More with Will Hill - Ep. 48 - Drew Dinsick

Bill@vsin.com (GoldBoys.com) — Fri, 3 May 2024 10:00:00 +0000

It's Derby time! The Kentucky Derby is tomorrow and to give his take on the race, Drew Dinsick (@whale_capper) of NBC Sports joins the pod with Will. The guys talk about how to bet the Derby, whether it's worth it to take the favorite, and the horses that may surprise. They also go over their plays for the NBA Playoff games today and a preview of the 2nd round along with some of their plays for those series. Don't miss out on the chance to bet these plays by tuning in!

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Shoulda Bet More with Will Hill - Ep. 47 - Brandon Anderson

Bill@vsin.com (GoldBoys.com) — Wed, 1 May 2024 10:00:00 +0000

In this episode of Shoulda Bet More, Brandon Anderson (@wheatonbrando) from Action Network joins the show to talk some NBA playoffs and some post-draft NFL. The Knicks were unable to close out their series last night, should they be worried going into game 6? The guys go through each of the still ongoing series and give their best bets on the each series and some props to play on the upcoming games. They also look ahead to the confirmed matchups in the next round and give their takes on the matchups. And finally, who are some of the teams to be looking at for futures plays post NFL draft and did the Vikings make the right call with JJ McCarthy as their future QB?

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Shoulda Bet More with Will Hill - Ep. 46 - Raheem Palmer

Bill@vsin.com (GoldBoys.com) — Mon, 29 Apr 2024 10:00:00 +0000

The NFL Draft is complete. The NBA Playoffs continue. Raheem Palmer from The Ringer (@iamrahstradamus) joins Will on this episode of the Shoulda Bet More podcast. Can the Sixers rally back against the Knicks? Can the Mavericks take down the Clippers? Is Lebron able to carry the Lakers to be the first team in the NBA to come back from being down three? Will the Cavs turn it around after losing two in a row? What two teams make it to the finals? What superstars will move this offseason? Tune in to hear what all these two have to share!

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Shoulda Bet More with Will Hill - Ep. 45 - Matkafee

Bill@vsin.com (GoldBoys.com) — Fri, 26 Apr 2024 10:00:00 +0000

Night one of the NFL Draft is in the books and boy was it chaotic. Here to recap and react to everything we just saw is Will and Matkafee (@matkafee) from GoldBoys. What did the guys think of the Michael Penix Jr. pick by the Falcons? What other surprises were there on night one? Who are the booms and busts from the first round? Plus, very early Offensive/Defensive Rookie of the Year betting looks! The guys also talk about some of their Friday NBA looks plus a look at each series and whether or not the team down in the series can mount a comeback. Tune in to get some of the best betting looks you can find on any podcast!

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Shoulda Bet More with Will Hill - Ep. 44 - Fred Segal (Freezing Cold Takes)

Bill@vsin.com (GoldBoys.com) — Wed, 24 Apr 2024 10:00:00 +0000

The NFL Draft is tomorrow and we are excited and ready to see who goes where! In this episode of Shoulda Bet More, Fred Segal of Freezing Cold Takes (@OldTakesExposed) comes on to talk about his new book, "Freezing Cold Takes: NFL: Football Media’s Most Inaccurate Predictions—and the Fascinating Stories Behind Them." They talk about the origin of the famous account, some of the NFL Draft's most freezing cold takes as well as some of the most freezing cold takes of all time! Plus, Will gives his mock top 10 picks and his Wednesday/Thursday picks for the NBA Playoffs!

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Shoulda Bet More with Will Hill - Ep. 43 - Kelley Bydlon

Bill@vsin.com (GoldBoys.com) — Mon, 22 Apr 2024 10:00:00 +0000

The NBA Playoffs have started and to talk what happened over the weekend, Kelley Bydlon (@KelleyBydlon) from VSiN's "A Numbers Game" returns to the pod! Will and Kelley talk about each series and what they've learned from the first batch of games. What would winning and losing mean to the teams in the playoffs? Which team has the best chance to upset the possible Nuggets/Celtics final? Plus, the guys talk the NFL Draft and talk about the possible draft order for the first couple of picks. Also, Will has a play he really likes for one of the Monday night playoff games! Tune in to get a leg up on your bets!

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Shoulda Bet More with Will Hill - Ep. 42 - Aaron Schatz

Bill@vsin.com (GoldBoys.com) — Wed, 17 Apr 2024 10:00:00 +0000

In the final episode before a mini break for the show, Will brings on Aaron Schatz of FTN Fantasy to talk the NFL offseason and the upcoming draft! The creator of DVOA goes over what teams he thinks have had good and bad offseason so far, where the rookie QBs may land, and what his models think various teams' win totals will be! Will also gives out some NFL draft looks for various teams that you may want to consider betting. Tune in to hear those bets and the opinions on the league that may help you to beat the books!

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Shoulda Bet More with Will Hill - Ep. 41 - Ryan Glasspiegel

Bill@vsin.com (GoldBoys.com) — Sun, 14 Apr 2024 10:00:00 +0000

The NBA season is about to draw to a close as Will welcomes Ryan Glasspiegel (@sportsrapport) from the New York Post onto the pod! We discuss the scenarios going into the last day of the season. The guys give their opinion on the state of the NBA while looking forward to the playoffs and discussing who they think will win it all. Also, after the Women's College Basketball final scored record viewership, will we see them continue to match or beat the men's viewership? Plus, the guys go over the various sports betting scandals and what that might mean for the leagues going forward. The guys also discuss some pre-draft NFL bets that they like for the upcoming season.

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Shoulda Bet More with Will Hill - Ep. 40 - Jason Weingarten

Bill@vsin.com (GoldBoys.com) — Fri, 12 Apr 2024 10:00:00 +0000

On this episode of Shoulda Bet More, Jason Weingarten (@Spreadapedia) from VSiN returns to the pod to talk some baseball. What's the latest on the Ohtani situation? Are the early season pitching injuries changing the way to bet Cy Young? What is going on with the Marlins? The guys also go through some of the teams playing well in the early season and say if they can keep it up for the rest of the year. They also discuss MLB awards bets, and even have an awards bet parlay to look out for! Plus, Will discusses the NBA Playoff landscape and how it might affect betting the playoffs. Tune in to get betting insight you can't anywhere else!

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Shoulda Bet More with Will Hill - Ep. 39 - Matt Youmans

Bill@vsin.com (GoldBoys.com) — Wed, 10 Apr 2024 10:00:00 +0000

Will is joined Matt Youmans of VSiN on this epsiode of the Shoulda Bet More podcast. UConn wins it all once again. With the college basketball season over, we now make our way over to Augusta for The Masters. Can Tiger hold up physically? Who does Matt have winning it all this year? The NFL Draft is quickly approaching. What quarterbacks are going where? Tune in to hear what all Will and Matt have to share!

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Shoulda Bet More with Will Hill - Ep. 38 - "The Bear" Chris Fallica

Bill@vsin.com (GoldBoys.com) — Mon, 8 Apr 2024 10:00:00 +0000

The Bear, Chris Fallica, makes a return to the Shoulda Bet More podcast. We're down to the final game of the NCAA tournament! UConn beat Alabama. Purdue beat NC State. With only two teams left, who will win it all? Does UConn beat Purdue to go back to back? What should the MLB do about all the pitcher injuries? Who does The Bear think will win The Masters? How many quarterbacks will be taken in the first round of the NFL Draft? Tune in to this episode to hear it all!

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Shoulda Bet More with Will Hill - Ep. 37 - Iain MacMillan

Bill@vsin.com (GoldBoys.com) — Fri, 5 Apr 2024 10:00:00 +0000

It's finally here, Final Four weekend. We have 3 games left in the tournament and to break down the semifinals games this weekend with Will, Iain MacMillan (@IainMacBets) from Betsided returns to the pod! The guys give their predictions for how they think the game will go, their leans on the Over/Unders and spreads, and their picks for Most Outstanding Player of the tournament! Plus, with the recent news of the Stefon Diggs trade to the Texans, how does that improve their team, and by extension, their Super Bowl odds? The guys break down the QBs who will be going in the NFL Draft and who you might be able to bet them going to. Exciting weekend to be betting, so tune in for the best advice!

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Shoulda Bet More with Will Hill - Ep. 36 - Todd Wishnev

Bill@vsin.com (GoldBoys.com) — Wed, 3 Apr 2024 10:00:00 +0000

We are drawing closer to Final Four weekend and to prepare, professional bettor, Todd Wishnev (@TWishnev), joins Will again on the pod! In it, they discuss where they lean on the spread and over/under for Alabama/UConn and NC State/Purdue. What does Todd think about this historic NC State run? Can Burnes compete with Edey and give Purdue fits? Will Alabama be able to stifle this dominant UConn team? Plus Todd give his personal betting tips for how to bet baseball, especially after this first weekend of games as well as some of his sneaky looks. Also, Will has a baseball futures longshot worth taking. Tune in to learn from one of the best and get ahead of the books!

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Shoulda Bet More with Will Hill - Ep. 35 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Mon, 1 Apr 2024 10:00:00 +0000

And then there were four, UConn, Alabama, Perdue and NC State! Jeff Parles of Sports by the Book returns to the pod to talk about what we witnessed the tournament games over the weekend and to give an early preview of the Final Four next week. How truly dominant is this UConn team? How historical of a run is this for NC State? Does Zach Edey get too many foul calls in his favor? Can this Alabama team prove to be a threat to UConn? Plus, what are the early thoughts after the first weekend and series of the MLB season? Can the Yankees keep the momentum until Cole is able to return? It's a packed episode, so tune in to hear all the advice the guys have to offer!

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Shoulda Bet More with Will Hill - Ep. 34 - Stuckey

Bill@vsin.com (GoldBoys.com) — Fri, 29 Mar 2024 10:00:00 +0000

On this episode of the Shoulda Bet More podcast, Stuckey, from Action Network, joins Will in breaking down the Sweet Sixteen! Will UConn be putting up another banner? Can Marquette take down NC State? Who comes out on top between Duke and Houston? Will Tennessee advance over Creighton? Did Ohtani know anything? Tune in to this episode to hear it all!

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Shoulda Bet More with Will Hill - Ep. 33 - Mitch Moss

Bill@vsin.com (GoldBoys.com) — Wed, 27 Mar 2024 10:00:00 +0000

We are just a day away from MLB Opening Day! We're excited and are ready to talk some baseball. Mitch Moss of "Follow the Money" on VSiN joins Will on this edition of Shoulda Bet More. We talk MLB futures, awards, as well as a look ahead to Thursday's games where Will gives you his leans! Plus, a sweet sixteen betting preview where you'll get best bets with the insights to back it up. Also, we're one month out from the NFL Draft, so what do we think the top 5 picks will look like?

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Shoulda Bet More with Will Hill - Ep. 32 - Jonathan Von Tobel

Bill@vsin.com (GoldBoys.com) — Mon, 25 Mar 2024 10:00:00 +0000

We are two rounds into March Madness and to go over the weekend's events with Will, Jonathan Von Tobel (@meJVT) of VSiN Primetime comes back to the pod! The guys go over what was a chalky weekend and talk about what surprised them, what they learned, and if they think better or worse of some of the remaining teams in the tournament. Also, an early look at the sweet sixteen lines to see what you should consider betting on. Plus the guys go over some updated NBA futures you might want to keep your eye on! Tune in to hear the takes that will best help you beat the books!

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Shoulda Bet More with Will Hill - Ep. 31

Bill@vsin.com (GoldBoys.com) — Fri, 22 Mar 2024 10:00:00 +0000

The first day of March Madness comes to a close. On this episode of the Shoulda Bet More Podcast, Will recaps day 1 of the NCAA tournament and covers some MLB as well as NFL. Oakland pulls off a massive upset against Kentucky. What does this mean for Calipari's future? Will touches on Friday's games and gives a lookahead to Saturday. Ohtani's interpreter is fired and accused of theft. Was this a coverup and secretly Ohtani betting? Some NFL free agency moves. Tune in to hear what all Will has to say!

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Shoulda Bet More with Will Hill - Ep. 30 - Iain MacMillan

Bill@vsin.com (GoldBoys.com) — Wed, 20 Mar 2024 10:00:00 +0000

The best time of the year for sports bettors has arrived! On this episode of the Shoulda Bet More Podcast, Will brings on Iain MacMillan, Senior Editor of Fansided and host of the Bacon Bets Podcast. The two discuss everything March Madness! Did the selection committee do a bad job? Are the Mountain West teams overhyped? Will there be any crazy upsets and what will they be? Is Auburn better than UConn? Tune in to hear what Will and Iani have to share!

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Shoulda Bet More with Will Hill - Ep. 29 - Kiev O'Neil

Bill@vsin.com (GoldBoys.com) — Mon, 18 Mar 2024 10:00:00 +0000

The committee has made their selections and the bracket is finally out! Kiev O'Neil from The OddsBreakers returns to the pod to discuss the early look at the bracket with Will. With so many bid steals, did the committee make the correct selections? Who got snubbed? Which teams should be on upset alert? The guys also give some early looks based on the lines that came out right after the bracket released. Also some tournament futures that are worth taking. Tune in to this episode to get an edge on the books on the best tournament of the year!

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Shoulda Bet More with Will Hill - Ep. 28 - Steve Fezzik

Bill@vsin.com (GoldBoys.com) — Fri, 15 Mar 2024 10:00:00 +0000

We are just three days away from Selection Sunday! To get ready for the NCAA Tournament, Steve Fezzik of Pregame.com comes back onto the pod to talk college hoops with Will. The guys discuss how to win your bracket pool, who to back and who to fade in the tournament, and how to manage your bankroll to maximize your chances of winning in the tournament. As a bonus, Steve also drops some NIT betting tips so you can get a little extra cash. Tune in to hear all of that and more on today's episode!

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Shoulda Bet More with Will Hill - Ep. 27 - Tim Kurkjian

Bill@vsin.com (GoldBoys.com) — Wed, 13 Mar 2024 17:10:45 +0000

With Opening Day only a couple weeks away, ESPN Analyst Tim Kurkjian joins Will to discuss some MLB! The Yankees continue to be plagued with injuries. Are the Guardians underrated and will they win the divison? How has no team gone after Blake Snell in free agency? Does the MLB need a different approach to their playoff format? Tim shares who he believes will be our 2024 World Series Champions. Tune in to hear everything Tim and Will have to say as we approach the start of the season!

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Shoulda Bet More with Will Hill - Ep. 26 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Mon, 11 Mar 2024 10:00:00 +0000

It's time for the major conference tournaments as Jeff Parles (@jeffparles) of Sports by the Book returns to the pod to discuss college hoops and a variety of other sports with Will! Who do the guys think from the bubble teams are in and out? Who should you be betting on in the upcoming conference tournaments? Did we see a NBA Finals preview last week in Nuggets/Celtics? How does the top 10 of the NFL draft pan out? Plus, with baseball coming up soon, where will Blake Snell sign and after the Senga injury, can the Mets make the postseason? Tune in to find out their opinions and to get a betting edge!

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Shoulda Bet More with Will Hill - Ep. 25 - Reed Wallach

Bill@vsin.com (GoldBoys.com) — Fri, 8 Mar 2024 11:00:00 +0000

March Madness is almost upon us! Reed Wallach, Senior Editor at BedSided joins Will to discuss everyones favorite college tournament on this episode of Shoulda Bet More! The two break down some of the conference tournaments they're looking at. How they approach the last regular season weekend. Is UConn going to win it all? Will Tennessee reach the Final Four? The two also discuss some NBA. Will the Nuggets and Celtics go up against eachother in the finals? Tune in to get a betting edge!

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Shoulda Bet More with Will Hill - Ep. 24 - Adnan Virk (Oscars Special)

Bill@vsin.com (GoldBoys.com) — Wed, 6 Mar 2024 11:00:00 +0000

The Oscars are this Sunday! To celebrate, we have this very special midweek episode of Shoulda Bet More! From Cinephile with Adnan Virk and MLB Network, Adnan Virk joins Will on the podcast. They discuss the various Oscars categories to try to find you an angle that you should be betting on, from the more well known categories to the smaller ones as well. In addition to the Oscars, the guys also talk baseball. Where will Blake Snell end up and are there any teams that can potentially surprise this season? Plus, where will Kirk Cousins and Justin Fields end up. Tune in for Will's takes and looks for you to get your betting edge!

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Shoulda Bet More with Will Hill - Ep. 23 - "The Bear" Chris Fallica

Bill@vsin.com (GoldBoys.com) — Mon, 4 Mar 2024 11:00:00 +0000

It's conference tournament week! To celebrate, from Fox Sports, and the host of the Bear Bets Podcast, "The Bear" Chris Fallica joins Will on this episode of Shoulda Bet More! They discuss who they think will be getting those coveted top seeds, who's in and who's out of the bubble teams, and potential NCAA Tournament prop looks. The guys also discuss MLB season props, the NFL draft, 2024 Heisman picks, and a special Champions League winner pick! Tune in to get an edge on what is going to be a fun March.

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Shoulda Bet More with Will Hill - Ep. 22 - Jason Weingarten

Bill@vsin.com (GoldBoys.com) — Fri, 1 Mar 2024 15:21:11 +0000

MLB spring training has arrived! Jason Weingarten joins Will on this episode of the Shoulda Bet More podcast to discuss the upcoming MLB season. With a month to go until opening day, the two cover what lines they're looking closely at. Does Yamamoto win NL Rookie of the Year? Will a team pick up Trevor Bauer before the start of the season? Who do they like to win the World Series? What odds are even worth it with how low some of the lines are. Tune in to hear it all!

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Shoulda Bet More with Will Hill - Ep. 21 - Jonathan Von Tobel

Bill@vsin.com (GoldBoys.com) — Mon, 26 Feb 2024 11:00:00 +0000

The host of VSiN Primetime, Jonathan Von Trobel (@meJVT), joins Will on this episode of Shoulda Bet More! They discuss NBA Award Futures and who is worth taking at the halfway point of the season as well as potential conference champion picks. They also talk NFL Free Agency and the NFL Draft. Plus, Will has a look for an NBA team not to make the playoffs and Will's college basketball takeaways from the weekend. Tune in to get a betting edge!

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Shoulda Bet More with Will Hill - Ep. 20 - Ian Eagle

Bill@vsin.com (GoldBoys.com) — Fri, 23 Feb 2024 11:00:00 +0000

Legendary CBS NFL, Final Four, and Brooklyn Nets play-by-play man, Ian Eagle, joins Will on this episode of Shoulda Bet More! They discuss the direction of the Nets, the landscape of college basketball as we head into March, his feelings on doing the Final Four play-by-play for the first time, and his thoughts on Mahomes, Rodgers, the 2023 NFL Season, and what the 2024 season might look like. Plus, Will addresses his jinx of UConn on Monday's episode, a look ahead to this weekend in college basketball, his thoughts on the NBA All-Star game, and a bonus TV recommendation!

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Shoulda Bet More with Will Hill - Ep. 19 - Todd Wishnev

Bill@vsin.com (GoldBoys.com) — Mon, 19 Feb 2024 11:00:00 +0000

Professional Bettor, Todd Wishnev, join Will on the Shoulda Bet More podcast to talk some college basketball. We discuss this weekend's results. Is UConn head and shoulders above the rest of the country? What is the best way to bet them for the NCAA Tournament. Speaking of the tournament, what other teams or longshots are worth betting? Which teams are overrated/underrated? How you should be looking to live bet college basketball games. Plus, what can be done about the NBA All Star Weekend to make it more interesting.

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Shoulda Bet More with Will Hill - Ep. 18 - Kelley Bydlon

Bill@vsin.com (GoldBoys.com) — Fri, 16 Feb 2024 11:00:00 +0000

On this episode of the Shoulda Bet More podcast, one final post mortem of the Super Bowl as Will reacts to the reaction of Kyle Shanahan's decision making. Kelley Bydlon (@KelleyBydlon) of VSiN join Will on the pod today to discuss the NBA. What are the bettable lines for NBA Awards including MVP? Should we be worried about the Nuggets? Which teams are contenders and which are pretenders? Plus some NBA All-Star weekend looks.

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Shoulda Bet More with Will Hill - Ep. 17 - Gill Alexander

Bill@vsin.com (GoldBoys.com) — Mon, 12 Feb 2024 11:00:00 +0000

In this post-Super Bowl LVIII edition of Shoulda Bet More, Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" joins the show in which he and Will give their raw reactions to what just happened. Where did Kyle Shanahan and the 49ers go wrong? Where does Patrick Mahomes rank among the greats? Where does Super Bowl LVIII itself rank? Find out the answers to these questions and many others by tuning in!

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Shoulda Bet More with Will Hill - Ep. 16 - Matt Hamilton

Bill@vsin.com (GoldBoys.com) — Fri, 9 Feb 2024 11:00:00 +0000

Matt Hamilton, Producer of the Up & Adams show on FanDuel TV, joins Will to discuss Super Bowl LVIII. Will finally has his pick on who he has winning. The two discuss their favorite picks ahead of the big game. Can San Francisco turn their defense around? Will the Chiefs be able to stop Christian McCaffrey? Matt expresses his love for nachos. Be sure to tune in!

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Shoulda Bet More with Will Hill - Ep. 15 - Jeff Parles

Bill@vsin.com (GoldBoys.com) — Mon, 5 Feb 2024 11:00:00 +0000

Jeff Parles of Sports by the Book joins the show to discuss his best bets on Super Bowl props, O/U, and his pick against the spread. How does Jeff feel about Dan Campbell's decision making in the NFC Championship Game? What is the go-to Super Bowl food choice? Will also gives his early week Super Bowl looks. Plus Jeff and Will talk baseball. How will Jeff's Mets fare this year? Can the Yankees win the pennant with the addition of Juan Soto? MVP Futures and O/U win totals on some teams. Tune in for some great betting insight!

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Shoulda Bet More with Will Hill - Ep. 14 - Kiev O'Neil

Bill@vsin.com (GoldBoys.com) — Fri, 2 Feb 2024 00:35:39 +0000

This episode Kiev O'Neil of The OddsBreakers, joins Will to discuss the Super Bowl as well as college basketball. Will we see the line move to three for the big game? Does Deebo Samuel have a shot at winning Super Bowl MVP? Kiev and Will share their thoughts and also dive deep into whats on the menu for their Super Bowl Party. Is North Carolina overrated? Is UConn the best team this year? Find out more by tuning in!

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Shoulda Bet More with Will Hill - Ep. 13 - Julian Edlow

Bill@vsin.com (GoldBoys.com) — Mon, 29 Jan 2024 19:19:55 +0000

Will sits down with Julian Edlow of the DraftKings Network to do a post-mortem on the Conference Championship games. Did Dan Campbell make the right calls to go for it? What happened to the Ravens? When should you be betting the Super Bowl spread and props and an early Super Bowl MVP look. Plus, who is going to be this year's Florida Atlantic in March Madness and is UConn the best team in the nation? Tune in to today's episode to get the betting edge.

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Shoulda Bet More with Will Hill - Ep. 12 - Drew Dinsick

Bill@vsin.com (GoldBoys.com) — Fri, 26 Jan 2024 14:02:15 +0000

In this episode of the Shoulda Bet More podcast, Drew Dinsick, NBC Sports analyst and co-host of the Bet The Edge podcast, joins Will to discuss the upcoming NFL Conference Championships this weekend. Patrick Mahomes extends his Conference Championship streak to six years. Will the Lions bring their amazing post-season run all the way to the Super Bowl? Does Lamar Jackson win MVP? Find out what Will and Drew are looking at by listening to this episode!

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Shoulda Bet More with Will Hill - Ep. 11 - Iain MacMillan

Bill@vsin.com (GoldBoys.com) — Mon, 22 Jan 2024 18:27:45 +0000

On this episode of the Shoulda Bet More Podcast, Senior Editor of Fansided and host of the Bacon Bets Podcast Iain MacMillan joins Will to discuss the Divisional Round and have an early look forward to the Conference Championship games. Plus a CBB futures bet that Iain thinks has value. Also, was this the last chance for the Bills? Are the 49ers able to preform without Deebo? Can the Lions win on the road? Do Mahomes and the Chiefs matchup well against the Ravens? Find out Will's thoughts by tuning in to today's episode!

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Shoulda Bet More with Will Hill - Ep. 10 - Stuckey

Bill@vsin.com (GoldBoys.com) — Fri, 19 Jan 2024 13:00:00 +0000

NFL Divisional Weekend is upon us and Will gives you his picks and his best bets for the weekend. Is bringing back Mike McCarthy a good idea for the Cowboys? From Action Network, Senior Betting Analyst, and the Prime Minister of Degenerate Nation, Stuckey comes onto the pod. Will and Stuckey go in depth game by game to give you the insights you need to bet this weekend's playoff games. Plus, who is the most underrated college basketball team this season?

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Shoulda Bet More with Will Hill - Ep. 9 - Jonathan Von Tobel

Bill@vsin.com (GoldBoys.com) — Mon, 15 Jan 2024 15:56:14 +0000

An exciting first weekend to the NFL playoffs. The Detroit Lions win their first playoff game in 32 years. The Packers upset the Cowboys. With two games left in the wild card round, Jonathan Von Tobel, Host & Senior NBA Betting Analyst at VSiN, joins Will to discuss what they are looking forward to tonight. Can the Eagles win without AJ Brown? Are the Bills able to lay ten even through the snowstorm? Will Belichick be headed to Dallas next season? What does JVT like in terms of NBA awards? Tune in to hear it all!

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Shoulda Bet More with Will Hill - Ep. 8 - The Hitman

Bill@vsin.com (GoldBoys.com) — Fri, 12 Jan 2024 18:06:45 +0000

The NFL Playoffs are officially here! We are 13 games away from knowing this years Super Bowl champion. The Hitman of Hammer Network and Pregame.com joins Will to discuss the wild card weekend. What teams should you look to bet? What are some good player props? Some big changes in terms of coaching as Belichick parts ways with the Patriots and the Seahawks let go of Pete Carroll. Nick Saban retires. Find out more by tuning in to this episode of the Shoulda Bet More podcast!

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Shoulda Bet More with Will Hill - Ep. 7 - Steve Fezzik

Bill@vsin.com (GoldBoys.com) — Mon, 8 Jan 2024 19:39:29 +0000

Steve Fezzik of Pregame.com joins the podcast to talk NFL Playoffs and his best bets, the National Championship Game, and how best to spend your Vegas trip with some Vegas hacks. Will goes through Week 18 and how it affects his picks going forward. Are Tua and Lawrence worth a second contract? Plus an early Wild Card Weekend preview and Will's National Championship Game best bet!

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Shoulda Bet More with Will Hill - Ep. 6 - Aaron Schatz

Bill@vsin.com (GoldBoys.com) — Fri, 5 Jan 2024 11:18:04 +0000

Aaron Schatz, Chief Analytics Officer at FTN Network, joins Will for this episode of the Shoulda Bet More podcast. With the final week of the NFL regular season upon us, what teams will move on to the postseason? What two teams do they think will be the Super Bowl finalists? Does the NFL need to change the playoff format? With so many good candidates, who wins Coach of the Year? So many questions answered on this episode so be sure to listen!

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Shoulda Bet More with Will Hill - Ep. 5 - Chris Fallica

Bill@vsin.com (GoldBoys.com) — Tue, 2 Jan 2024 21:27:19 +0000

The Bear, Chris Fallica, joins Will in this episode of the Shoulda Bet More podcast. Two great college football games to start off 2024. Does Washington win it all against Michigan to give the Pac-12 a final farewell? What are Chris and Will looking towards as we approach the final week of the NFL regular season? Chris gives his predictions for the 2024 Sentry tournament. Tune in to hear what all they have to say!

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Shoulda Bet More with Will Hill - Ep. 4 - Mike Sando

Bill@vsin.com (GoldBoys.com) — Fri, 29 Dec 2023 22:00:36 +0000

In this episode of the Should've Bet More podcast, Mike Sando, NFL Senior Writer at The Athletic, joins Will to discuss NFL, college football, and some awards. We have a big weekend ahead of us for college football. Does Alabama beat Michigan? Who comes out on top between Texas and Washington? Is Damar Hamlin still going to win Comeback Player of the Year or did Joe Flacco steal it from him with last nights performance against the Jets? With only two weeks left in the NFL regular season, tune in to this episode to hear what they have to say!

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Shoulda Bet More with Will Hill - Ep. 3 - 12/26

Bill@vsin.com (GoldBoys.com) — Tue, 26 Dec 2023 21:25:07 +0000

In this episode of the Shoulda Bet More podcast, Will looks back at the week 16 NFL slate and what that means for futures bets. Will also talks to Jason Weingarten (@Spreadapedia)of VSiN about NFL Awards bets and MLB futures after the big signings by the Dodgers. If you want some great insight on what to be betting on, check out this today's episode!

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Shoulda Bet More with Will Hill - Ep. 2 - 12/22

Bill@vsin.com (GoldBoys.com) — Fri, 22 Dec 2023 18:21:03 +0000

In this episode of the Shoulda Bet More podcast, Will dives into the week 16 NFL games. What's the final playoff picture going to look like as we head into Christmas weekend? Bowl games continue. Yamamoto finally makes a decision. The Dodgers are building a super team. If you want to hear more, check out this weeks episode!

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Shoulda Bet More with Will Hill - Ep. 1 - 12/18

Bill@vsin.com (GoldBoys.com) — Fri, 22 Dec 2023 18:17:38 +0000

Premiere episode of the Shoulda Bet More Podcast with Will Hill brought to you by the GoldBoys Network! This debut episode features a guest spot by Gil from VSiN!

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