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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. 246 Gill Alexander Oct 06, 2025

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Yankees brutal weekend up north, looks ahead to Game 3, and recaps the day in the NFL. Then, Gill Alexander of A Numbers Game joins to try to make sense of the Arizona Cardinals collapse, discuss if the Ravens are done, and give his thoughts on Monday's MLB and NFL games.

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Shoulda Bet More with Will Hill - Ep. 245 Ben Wilson Oct 03, 2025

Show notes

On this episode of the Shoulda Bet More podcast, Will reacts to the Yankees beating the Red Sox, looks ahead to the ALDS and NLDS, and Ben Wilson joins to discuss the MLB playoffs, 49ers/Rams, and his NFL picks for the weekend.

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Shoulda Bet More with Will Hill - Ep. 244 Jeff Parles Oct 01, 2025

Show notes

On this episode of the shoulda bet more podcast will hill recaps a brutal Yankees loss to the Red Sox, previews game 2 , and gives his best bets for Tuesday . Then, Jeff Parles from sports by the book joins to discuss the day in MLB, Wednesdays games, NFL takeaways 4 weeks in and more

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Shoulda Bet More with Will Hill - Ep. 243 Nic Larson Sep 29, 2025

Show notes

On this episode of the Shoulda Bet more Podcast, Will Hill reacts to Sunday's NFL action and discusses the Chiefs win over the Ravens. Plus, MLB handicapper Nic Larson joins the show to discuss the MLB playoffs and give his best bets.

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Shoulda Bet More with Will Hill - Ep. 242 Brad Powers Sep 26, 2025

Show notes

On this episode of the Shoulda Bet More Podcast, Will Hill gives his college football and NFL picks for the weekend. Then Pro Bettor Brad Powers joins to discuss all the big college games this weekend, his best bets, and his thoughts on the Heisman and National title picture.

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Shoulda Bet More with Will Hill - Ep. 241 Dave Ross Sep 24, 2025

Show notes

On this episode of the Shoulda Bet More podcast , Will Hill recaps a wild Tuesday night in MLB, gives a handful of Best Bets for Wednesday, then Dave Ross of VSiN By The Books joins to discuss the Mets crazy comeback, who gets the final NL Wild card spot , futures odds, and more.

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Shoulda Bet More with Will Hill - Ep. 240 Jensen Lewis Sep 22, 2025

Show notes

On this episode of Shoulda Bet More, Will Hill recaps a wild day in the NFL, previews Monday Night Football, and breaks down the MLB playoff picture as we enter the final week of the season. Plus, Jensen Lewis from VSiN By The Books joins the show to discuss MNF, recap today's NFL action and which teams will make the MLB Playoffs.

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Shoulda Bet More with Will Hill - Ep. 239 Adam Kaufman Sep 19, 2025

Show notes

On this episode of Shoulda Bet More, Will Hill takes a look at the Sunday NFL Week 3 slate and gives out his best bets. Then, Adam Kaufman of Your Betting News joins to give out his NFL Week 3 picks, plus talk about the Red Sox making the postseason this year.

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Shoulda Bet More with Will Hill - Ep. 238 Sammy P Sep 17, 2025

Show notes

On this episode of the shoulda bet more podcast Will Hill takes a look at the MLB playoff picture and World Series odds and gives out a best bet for TNF. Then, Sammy P of Fox sports joins to discuss lack of NFL Upsets , this weeks games , futures + More

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Shoulda Bet More with Will Hill - Ep. 237 - Stormy Buonantony Sep 15, 2025

Show notes

On this episode of the Shoulda Bet More Podcast, Will Hill reacts to the Week 2 of the NFL, discusses the possibility of the Chiefs missing the playoffs and previews Monday Night Football. Then, Stormy Buonantony from ESPN and VSiN joins to discuss the NFL, her Monday Night Football picks, thoughts on college football, the best restaurants in college towns and more.

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