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Shoulda Bet More — Sports
Shoulda Bet More

Ever have that gut feeling and wish you’d bet more? This is the podcast for you. Join VSiN and Fox Sports contributor Will Hill as he breaks down the biggest betting news and reveals the sharpest plays across the sports world. Each episode is a deep dive into betting strategies, odds analysis, and the data you need to find an edge.

Whether it’s NFL, NBA, MLB, or college football, we’ll tell you which side to be on and why. From dissecting the latest line moves to uncovering valuable props and futures, Will and his guests—the best minds in sports betting—ensure you’re always one step ahead.

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Latest Episodes:

Shoulda Bet More with Will Hill - Ep. 365 Sammy P Jul 17, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill previews the World Cup Final and looks ahead to the 2nd half of the MLB season. Plus, Sammy P from Fox Sports joins to discuss Spain-Argentina, MLB bets, NFL futures and food in Chicago.

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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 364 Jeff Parles Jul 15, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the home run derby and previews the World Cup Semifinal between England-Argentina. Plus, Jeff Parles from ESPN Las Vegas joins to discuss the World Cup, MLB trade deadline and MLB futures.

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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 363 Dave Ross Jul 13, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill takes a look around Major League Baseball heading into the break, as well as the Home Run Derby and All-Star game. Also on the show, VSiN By The Book and First Strike podcast co-host, Dave Ross, drops by to chat MLB storylines and futures, UFC, an early look at the NFL and 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 promo code: POD26. Click Here to get started.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 362 Brad Thomas Jul 10, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill looks at an overview of the MLB season entering all star weekend, then Brad Thomas of CBS Sports joins to preview the weekend action in the World Cup.

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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 361 Julian Edlow Jul 08, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill previews the Wednesday MLB games, including a best bet. Then Julian Edlow of DraftKings joins to discuss the nba summer league and offseason moves, as well as some college football bets 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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 360 Chris Fallica Jul 06, 2026

Show notes

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.

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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 359 Mitch Moss Jul 03, 2026

Show notes

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

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 358 Jeff Parles Jul 01, 2026

Show notes

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.

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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 357 John Jastremski Jun 29, 2026

Show notes

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.

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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 356 Steve Phillips Jun 26, 2026

Show notes

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.

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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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