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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. 384 Jonathan Von Tobel Sep 04, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives his take on Kawhi Leonard and the Clippers sanctions, and Jonathan Von Tobel joins to break down week 1 of college football, the Kawhi news, survivor strategy, and more.

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Shoulda Bet More with Will Hill - Ep. 383 Kiev O'neil Sep 02, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill looks ahead to Week 1 in college football, and Kiev O’Neil of the Oddsbreakers joins to discuss his favorite bets in the NFL and college football

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Shoulda Bet More with Will Hill - Ep. 383 Brad Thomas Aug 31, 2026

Show notes

On this episode the Shoulda Bet More podcast Will Hill recaps week 0 in college football and looks ahead to Week 1. Then Brad Thomas of CBS Sports joins to review week 0, and discuss his best bets in college and the NFL

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Shoulda Bet More with Will Hill - Ep. 382 Stormy Buonantony Aug 28, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill breaks down week 0 of the college football season, and Stormy Buonantony of Money Moves and ESPN joins to discuss her NFL bets, the college football season, and more.

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Shoulda Bet More with Will Hill - Ep. 381 Dave Ross Aug 26, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill talks Week 0 in college football, then Dave Ross of VSiN By The Books joins to discuss his NFL thoughts, mlb races, and his courting of Charlize Theron.

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Shoulda Bet More with Will Hill - Ep. 380 Chris Fallica Aug 24, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill recaps week 2 of the preseason, and Chris "The Bear" Fallica of Fox Sports joins to discuss his best bets in college football, MLB pennant races, the U.S. Open, and more.

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Shoulda Bet More with Will Hill - Ep. 379 Gill Alexander Aug 21, 2026

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On this episode of the Shoulda Bet More podcast, Will Hill looks at the weekend in MLB, then Gill Alexander of A Numbers Game joins to discuss his process prepping for football season, thirst traps, MLB races, the US Open and more.

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Shoulda Bet More with Will Hill - Ep. 378 Jensen Lewis Aug 19, 2026

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On this episode of the Shoulda Bet More podcast, Will Hill discusses Max Fried’s injury and its impact on the Yankees' futures prices. Then, Jensen Lewis of Vsin By The Books joins to look at the playoff races, awards, and all things baseball.

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Shoulda Bet More with Will Hill - Ep. 377 Brett Ciancia Aug 17, 2026

Show notes

On this episode of the shoulda bet more podcast, Will Hill takes a look at the MLB races and reacts to the first of the NFL preseason. Then Brett Ciancia of Pick Six Previews joins to give his best bets for the upcoming college football season.

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Shoulda Bet More with Will Hill - Ep. 376 Mike Sando Aug 14, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives out some MLB Futures, and then Mike Sando of the Athletic joins to discuss his annual NFL QB Tiers column.

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