Explore every episode of the podcast Shoulda Bet More

On this episode of Shoulda Bet More, Will Hill chats the World Cup and the latest headlines around Major League Baseball. Also on the show, Chris Fallica from FOX Sports and the Bear Bets Podcast joins to break down the World Cup, USA's chances vs. Belgium, MLB, football and more.

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On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Jaylen Brown trade and discusses the struggling Yankees. Then, Mitch Moss of Follow the Money joins to discuss the NBA offseason,  the World Cup, 4th of July food, and more

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On this episode of the Shoulda Bet More podcast, Will Hill breaks down the U.S. Soccer matchup Wednesday and LeBron James leaving the Lakers. Then, Jeff Parles of ESPN Las Vegas joins to discuss the World Cup, NBA Offseason, the struggling Yankees, and more.

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On this episode of Shoulda Bet More, Will Hill reacts to the World Cup and the latest headlines around Major League Baseball. Also on the show, VSiN contributor and "New York, New York" show host John Jastremski hops on to chat MLB storylines, including favorites in the AL and NL and Cy Young races, future picks for the NFL and more.

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On this episode the Shoulda Bet More Podcast, Will Hill reacts to the NBA Draft and recent blockbuster trades. Plus, Will is joined by MLB Network Host and former Mets GM Steve Phillips. The guys discuss the MLB trade deadline, 2nd half of the MLB season, destination for Tarik Skubal and labor negotiations.

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On this episode the Shoulda Bet More podcast Will Hill gives his finals thoughts on the NBA Draft. Then, expert draft bettor Luke Swain (Vegas Refund) joins to give out best bets for the NHL and NBA Draft, and breaks down what surprises we could get. 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 here to get started.

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On this episode of the Shoulda Bet More podcast, Will Hill gives his take on the NBA Draft and some ways to bet the futures market. Also on the show, VSiN's A Numbers Game co-host Gill Alexander joins the show to chat MLB futures in the American and National League, World Cup action, French Open, NBA Draft, movies to watch right now and more.

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On this episode of the Shoulda Bet More podcast, Will Hill gives his take on when and where Giannis will get traded. Then, Dave Ross of VSIN By The Books joins to discuss the U.S. Open, the World Cup, MLB Bets, and more.

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On this episode of the Shoulda Bet More podcast, Will Hill looks ahead to the NBA Draft and gives a long shot NFL Award bet. Then, from Fox Sports is Geoff Schwartz, former NFL offensive lineman joins to discuss the World Cup, NFL, and College and Football bets, tv shows to catch up on during the summer, and more.

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On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Knicks winning the NBA Finals and whether or not the Spurs blew it on the way. Also on the show, Chris "The Bear" Fallica joins to chat the NBA Finals and next year's futures, Monday's World Cup matchups, MLB outlooks, U.S. Open, early Heisman odds and more.

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On this episode of the Shoulda Bet More podcast, Will Hill reacts to an epic Game 4 of the NBA Finals and the Knicks making a historic comeback against the Spurs, then what to bet in Game 5. Also on the show, VSiN By The Books co-host Jensen Lewis joins to chat the NBA Finals, College World Series and MLB.

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On this episode of the Shoulda Bet More podcast, Will Hill reacts to Game 3 of the NBA Finals and looks ahead to Game 4. Plus, Kelley Bydlon from a A Numbers Game joins to discuss all things NBA Finals, the Draft and offseason.

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On this episode of the Shoulda Bet More podcast, Will Hill recaps the Knicks taking a 2-0 series lead in the NBA Finals and if the Spurs have any chance at making a comeback, as well as a tied series in the Stanley Cup Final. Also on the show, Jeff Parles from ESPN Las Vegas drops by with his thoughts on the Finals, storylines around the Knicks and Spurs and headlines around Major League Baseball.

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On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Knicks Game 1 victory in the NBA Finals and looks ahead to Game 2. Then, Jonathan Von Tobel of Money Moves joins to break down the NBA Finals, discuss a few sleepers for MVP of the series, and talk NBA Draft betting.

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On this episode of the Shoulda Bet More podcast, Will Hill gives his thoughts on the NBA Finals and the Aaron Judge injury’s impact on the AL MVP race. Then, pro sports bettor Chris Macero joins to talk Knicks / Spurs, the Stanley Cup Final, the Belmont, and more.

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On this episode of the Shoulda Bet More podcast, Will Hill previews the NBA Finals between the Spurs and Knicks and some trends and numbers around the series. Also on the show, Kiev O'Neil from The Odds Breakers hops on to break down all things NFL, including division previews, team and player props, and a little college football for good measure.

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On this episode of the Shoulda Bet More podcast, Will Hill reacts to another blowout in the Western Conference Finals, and then Gill Alexander of A Numbers Game joins to preview Game 7, discuss the French Open, MLB bets + more 

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On this episode the Shoulda Bet More podcast, Will Hill reacts to the Knicks making the NBA Finals and discusses their chance in the NBA Finals. Then, Jensen Lewis of ESPN and VSIN By the Books joins to talk MLB awards, futures, the College Baseball NCAA Tournament, and more.

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On this episode of the Shoulda Bet More podcast, Will Hill previews the NBA Conference Finals and if the Knicks have a shot at winning it all. Also on the show, sports betting analyst Doug Kezirian joins the show to discuss the playoffs, NBA free agency potential moves, NFL ramping up and the WNBA.

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On this episode of the Shoulda Bet More podcast, Will Hill previews Game 3 of Spurs / Thunder and shares his thoughts on some MLB storylines entering the weekend. Then, Brad Thomas of CBS Sports joins to break down the NBA and NHL Playoffs, the World Cup, and more.

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On this episode of the Shoulda Bet More podcast, Will Hill previews Game 2 of Spurs / Thunder and relives a classic Game 1. Then, Jonathan Von Tobel of Money Moves joins to discuss the Conference Finals, the NBA offseason, NFL early thoughts, and more.

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On this episode of the Shoulda Bet More podcast, Will Hill previews the Conference Finals for the NBA playoffs, including the Spurs chances against the Thunder and if the Knicks are a lock to make it to the Finals, as well as some MLB talk. Also on the show, Chris "The Bear" Fallica from FOX Sports joins the show to chat the NBA, NFL storylines and futures, his favorite college football over/unders and how to bet the World Cup.

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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

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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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.

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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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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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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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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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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.

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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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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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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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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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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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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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