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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. 276 Gill Alexander Dec 15, 2025

Show notes

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 Dec 12, 2025

Show notes

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 Dec 10, 2025

Show notes

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 Dec 08, 2025

Show notes

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 Dec 05, 2025

Show notes

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 Dec 03, 2025

Show notes

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 Dec 01, 2025

Show notes

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 Nov 28, 2025

Show notes

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 Nov 26, 2025

Show notes

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 Nov 24, 2025

Show notes

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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