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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. 394 Kiev O'Niel Sep 28, 2026

Show notes

In this episode of the Shoulda Bet More podcast, Will Hill is joined by Kiev O’Neil of the Oddsbreakers as they recap all the action we saw in Week 3 of the NFL season and look ahead to the Monday Night Football game between the Bears and Eagles.

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Shoulda Bet More with Will Hill - Ep. 393 Jonathan Von Tobel Sep 25, 2026

Show notes

On this episode of the shoulda bet more podcast Will gives his picks in NFL and college, then Jonathan Von Tobel choice to discuss his best bets in the NFL and a loaded college slate.

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Shoulda Bet More with Will Hill - Ep. 392 Chris Fallica Sep 23, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill reacts to the Jackson Dart injury and evaluates the Giants options, and gives a preview and best bet for TNF. Then Chris Fallica, the Bear, of Fox sports joins to break down a great weekend of college football, as well as bets in MLB and NFL that he’s eying.

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Shoulda Bet More with Will Hill - Ep. 391 Gill Alexander Sep 21, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill reacts to a wild week 2 in the NFL, and Gill Alexander joins to recap the games , preview MNF and look ahead to next week.

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Shoulda Bet More with Will Hill - Ep. 390 Jeff Parles Sep 18, 2026

Show notes

On this episode of the shoulda bet more podcast Will Hill gives his NFL week 2 picks , then Jeff parles of espn Las Vegas joins to recap lions Bills and look ahead to week 2 and preview the final week of the mlb season

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Shoulda Bet More with Will Hill - Ep. 389 Dave Ross Sep 16, 2026

Show notes

On this episode of the shoulda been more podcast Will Hill previews Thursday night football between the Lions and Bills with a best bet , and Dave Ross, of VSiN By the Books joins to look ahead to week two in the NFL

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Shoulda Bet More with Will Hill - Ep. 388 Geoff Schwartz Sep 14, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill reacts to Week 1 of the NFL and looks ahead to to MNF. Then, Geoff Schwartz of Fox Sports joins to recap the week, look ahead to Week 2 , and react to Oregon’s loss

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Shoulda Bet More with Will Hill - Ep. 387 Dustin Swedelson Sep 11, 2026

Show notes

On this episode of the shoulda bet more podcast Will Hill breaks down week 1 of the nfl and reacts to the first 2 games. Then Dustin Swedelson of Cashing out joins to discuss the nfl, his best bets in college and the mlb races.

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Shoulda Bet More with Will Hill - Ep. 386 Jensen Lewis Sep 09, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill gives his NFL Division and SB Picks + best bet for Pats/ Seahawks . Then Jensen Lewis joins to give week 1 nfl picks , week 2 college picks , discuss mlb playoff races + more.

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Shoulda Bet More with Will Hill - Ep. 385 Jeff Parles Sep 07, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill reacts to the controversial ending in the Michigan win, and recaps the rest of Week 1 while looking ahead to Week 2. Then, Jeff Parles of ESPN Las Vegas joins to discuss his bets in College football , the NFL and the MLB races.

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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