• Shoulda Bet More with Will Hill - Ep. 401 Dave Ross
    Oct 14 2026

    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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    41 Min.
  • Shoulda Bet More with Will Hill - Ep. 400 Gil Alexander
    Oct 12 2026

    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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    38 Min.
  • Shoulda Bet More with Will Hill - Ep. 399 Matt Youmans
    Oct 9 2026

    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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    48 Min.
  • Shoulda Bet More with Will Hill - Ep. 398 Mitch Moss
    Oct 7 2026

    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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    37 Min.
  • Shoulda Bet More with Will Hill - Ep. 397 John Jastremski
    Oct 5 2026

    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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    32 Min.
  • Shoulda Bet More with Will Hill - Ep. 386 Jensen Lewis
    Sep 9 2026

    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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    35 Min.
  • Shoulda Bet More with Will Hill - Ep. 385 Jeff Parles
    Sep 7 2026

    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.


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    34 Min.
  • Shoulda Bet More with Will Hill - Ep. 384 Jonathan Von Tobel
    Sep 4 2026

    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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    38 Min.