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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. 406 Chris Fallica Oct 28, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill recaps a wild Rays comeback and Chris Fallica of Fox Sports joins to discuss the CFB slate, the playoff picture , NFL bets and more.

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Shoulda Bet More with Will Hill - Ep. 405 Jeff Parles Oct 26, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill recaps the day in the NFL and looks ahead to Mondays games. Then Jeff Parles of ESPN Las Vegas joins to react to the day in football , discuss the World Series, college football and more.

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Shoulda Bet More with Will Hill - Ep. 404 Jensen Lewis Oct 23, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill previews the World Series and give his football picks for the weekend . Then Jensen Lewis of vsin by the books joins to break down the fall classic, sleeper mvp bets and more.

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Shoulda Bet More with Will Hill - Ep. 403 Kiev O'Neil Oct 19, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill recaps a wild weekend of football and looks ahead to MNF. Then, Kiev O’Niel of the Oddsbreakers joins to discuss all the action, analyze the futures and awards markets and try to make sense of all the upsets in College Football.

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. 402 Ben Wilson Oct 16, 2026

Show notes

On this episode of the shoulda bet more podcast Will Hill reacts to the Brewers sweeping the Dodgers and another OT NFL primetime game. Then Ben Wilson of Fox sports joins to react to the Brewers NL title , look ahead of the World Series and give his favorite plays of the weekend.

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. 401 Dave Ross Oct 14, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill recaps a wild Bills victory over the Rams and previews Seahawks/Broncos. Then, Dave Ross of VSIN By the Books joins to give his thoughts on the NFL through 5 weeks, look at his best bets for Week 6, and discuss the NLCS.

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Shoulda Bet More with Will Hill - Ep. 400 Gill Alexander Oct 12, 2026

Show notes

On this episode of the shoulda bet more podcast, Will Hill recaps another wild day in the NFL, and looks ahead to Monday night football and the ALCS. Then Gill Alexander of a numbers game joins to review the day that was in NFL and give his thoughts on the MLB playoffs

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Shoulda Bet More with Will Hill - Ep. 399 Matt Youmans Oct 09, 2026

Show notes

On this episode of the shoulda bet more podcast Will Hill reacts to the Yankees getting swept by the Rays and gives his thoughts on the NFL + CFB games this weekend. Then Matt Youmans of vsin primetime joins to recap the Yankees exit , preview dodgers brewers and give his best bets for the weekend

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Shoulda Bet More with Will Hill - Ep. 398 Mitch Moss Oct 07, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill previews the day in MLb playoffs and gives a couple of NFL best bets. Then Mitch Moss of follow the money joins to discuss the NFL futures and awards market and give his thoughts on week 5

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Shoulda Bet More with Will Hill - Ep. 397 John Jastremski Oct 05, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill recaps a wild Week 4 in the NFL and looks ahead to the Monday action. Then, John Jastremski of SNY joins to discuss the Yanks Rays series and react to the day that was in the NFL.

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