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PODCAST

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

sports football

All Episodes

30:14

Shoulda Bet More with Will Hill - Ep. 173 - John...

Shoulda Bet More ·

2025/02/21

Today, we continue getting ready for baseball at the beginning of Spring Training and we brought back John Jastremski (@john_jastremski) of The Ringer to get his thoughts on the upcoming season! We discuss the AL and NL East as they figure to be the divisions that could go down to the wire this season and try to project who will come out on top. We also discuss win totals for some of those teams to see if they are worth betting. We take a broader look at the league as well to see who some

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36:44

Shoulda Bet More with Will Hill - Ep. 172 - Dustin...

Shoulda Bet More ·

2025/02/19

On today's episode of Shoulda Bet More, we start talking baseball with Dustin Swedelson (@dustinswedelson) from SiriusXM Mad Dog Sports Radio and VSiN! We get his takes on who the best teams are in the AL and the NL, the sleepers in the divisions, and his favorite longshots to win the World Series! We go over offseason questions for the Mets, Yankees, Red Sox, and more and see if they've improved enough to be major forces this season. We also touch on the NFL offseason to take a temperature

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33:21

Shoulda Bet More with Will Hill - Ep. 171 - Todd Wishnev

Shoulda Bet More ·

2025/02/17

We are just weeks away from conference tournaments and the NCAA Tournament to crown the champion of college basketball. To get us ready for the postseason, we've invited Todd Wishnev (@TWishnev) back to the pod! We recap the Auburn vs. Alabama game from the weekend and discuss whether or not anyone can stop Auburn or if they are just too dominant. We talk about some of the top teams from each of the conferences and wonder how far in the tournament they can go and what weakness could prevent

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30:12

Shoulda Bet More with Will Hill - Ep. 170 - Brad Thomas

Shoulda Bet More ·

2025/02/14

The Genesis Open in LA is this weekend, and to get some advice on how to bet it, we've brought Brad Thomas (@MrBradThomas) from NBC Sports and MGM Network back to the podcast! We pick his brain about who he likes to win the tournament and who he thinks is worth a flier. We also get his opinions on what has changed in the NBA after the trade deadline and if any team can stop the Thunder and Celtics from ending up in the Finals. We also talk a little NFL offseason and whether or not older QB

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36:08

Shoulda Bet More with Will Hill - Ep. 169 - Geoff...

Shoulda Bet More ·

2025/02/12

On today's episode of Shoulda Bet More, we continue to dive into the Super Bowl postmortem. Who better to bring on to talk football than a former NFL Offensive Lineman in Geoff Schwartz (@geoffschwartz) from Fox Sports! We go in-depth on how the Eagles thoroughly dismantled the Chiefs. How much blame should Patrick Mahomes shoulder in the loss? What can we takeaway from the construction of this Eagles roster and what will other teams to do copy its success? We also begin to look forward to

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49:21

Shoulda Bet More with Will Hill - Ep. 168 - Gill...

Shoulda Bet More ·

2025/02/10

The Philadelphia Eagles are your Super Bowl LIX champions, and they won in a dominant fashion. We've invited Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" back to the pod to get his and Will's instant reaction to what we just witnessed. How did the Eagles manage to put away the Chiefs by halftime? Is this the end of the Chiefs dynasty? Do we rethink how truly good some of the other teams around the league are after this performance by the Eagles? We

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35:01

Shoulda Bet More with Will Hill - Ep. 167 - Sammy P

Shoulda Bet More ·

2025/02/07

We are just 2 days away from the Super Bowl. We continue our coverage of it today by bringing from the Chicken Dinner podcast, BetMGM, and Fox Sports, Sammy P (@spshoot)! We get Sammy's perspective on how the game will go down and the bets that he is placing because of it. In addition, Will gives the plays that he's locking in for Sunday. We also talk some college basketball to see what sleepers and longshots could go to the Final Four in March. We also discuss some baseball and have a

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40:46

Shoulda Bet More with Will Hill - Ep. 166 - Kiev O'Neil

Shoulda Bet More ·

2025/02/05

Today, we are kicking our Super Bowl coverage into high gear by bringing back Kiev O'Neil (@OBKiev) of The Odds Breakers to the pod! We take a deep dive into Sunday's game by looking at each of the main markets in-depth and the best player props that stick out to us. Kiev gives us his methods of attacking Super Bowl betting so he can end the biggest game of the year on top. We also talk about the best foods to have while watching the Super Bowl! We also get into late season College

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41:15

Shoulda Bet More with Will Hill - Ep. 165 - Jeff Parles

Shoulda Bet More ·

2025/02/03

Welcome to Shoulda Bet More, your go-to podcast for all things sports! In this episode, we dive into the upcoming Super Bowl, breaking down the key matchups and what to expect. Plus, we’re talking about the jaw-dropping NBA trade that’s shaking up the league: Anthony Davis for Luka Dončić. You won’t want to miss this one. Tune in!

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27:39

Shoulda Bet More with Will Hill - Ep. 164 - Jason...

Shoulda Bet More ·

2025/01/31

We are nearing the date of pitchers and catchers arriving for Spring Training. To get ready for that date, we've brought back Jason Weingarten (@Spreadapedia) of VSiN to give us his outlook on the upcoming season of baseball. We get his reaction to the offseason moves and how he feels about the Dodgers spending money on their free agents. We get Jason's favorite future bets for this season with the offseason coming to a close. We take a quick discussion of awards futures to see if there are

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33:57

Shoulda Bet More with Will Hill - Ep. 163 - Kelley...

Shoulda Bet More ·

2025/01/29

With the NFL in a hibernation period until the Super Bowl, we turn our eyes to NBA basketball! To get a temperature of where we are at in the middle of the season, we've invited Kelley Bydlon (@KelleyBydlon) from VSiN's "A Numbers Game!" Is a Celtics vs. Thunder Final inevitable? Which teams have the best chance of stopping it come playoffs? What trades could we possibly see as we approach the midseason mark? Plus, who are the front runners for awards and what longshots could surprise? We

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38:52

Shoulda Bet More with Will Hill - Ep. 162 - Jonathan...

Shoulda Bet More ·

2025/01/27

Shoulda Bet More is the ultimate podcast for NFL fans who love the thrill of the game and the excitement of placing a bet. Join Will Hill and returning guest JVT as they break down the Conference Championship games, analyzing key plays, standout performances, and those crucial moments that made or broke the odds. Get expert takes on the big game, plus insider tips and predictions for the upcoming Super Bowl showdown. Whether you’re a casual fan or a die-hard gambler, Shoulda Bet More is the

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25:56

Shoulda Bet More with Will Hill - Ep. 161 - Dave Ross

Shoulda Bet More ·

2025/01/24

It's Conference Championship weekend, and we are continuing to go to VSiN collaborators to get the best in-depth look look at the games by inviting back Dave Ross (@drosssports)! We take a deep dive into the Commanders vs. Eagles and the Bills vs. Chiefs and give you our favorite props and leans. We try to get Dave's picks for the weekend and for who he thinks will win the Super Bowl in two weeks! Lastly, we get Dave's reaction to how the Mets have done this offseason beyond the Juan Soto

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43:13

Shoulda Bet More with Will Hill - Ep. 160 - Matt Youmans

Shoulda Bet More ·

2025/01/22

With the National Championship Game in the rear-view, we only have 3 football games remaining. To discuss what we've seen and what we will see, we've brought back from VSiN, Matt Youmans (@mattyoumans247)! We go over Ohio State's victory against Notre Dame to put a bow on a great College Football season. We preview Conference Championship weekend in the NFL by discussing our favorite bets so far with these early lines. Can the Bills finally overcome Patrick Mahomes and Chiefs in the

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48:06

Shoulda Bet More with Will Hill - Ep. 159 - Jeff Parles

Shoulda Bet More ·

2025/01/20

What a great weekend of football we had, but we aren't done yet! Today is the National Championship game between Ohio State and Notre Dame. To give us his betting looks for the game, we've invited back Jeff Parles (@jeffparles) from "Sports By The Book!" We do a deep dive into the game and give you our favorite to win and our betting leans that show where we think this game is headed. We also recap an awesome divisional round and get into the upsets and controversies from the weekend. Is

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30:49

Shoulda Bet More with Will Hill - Ep. 158 - John...

Shoulda Bet More ·

2025/01/17

It's Divisional Round weekend! To expand on what we were talking about with early previews on Wednesday's episode, we've brought back John Jastremski (@john_jastremski) of The Ringer to give us more betting viewpoints of this weekend's games! We do an in-depth dive on Texans/Chiefs, Commanders/Lions, Rams/Eagles, and Ravens/Bills, giving your our favorite betting looks in each game and who we ultimately think we will be seeing in the Conference Championships! We discuss some of the coaching

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32:57

Shoulda Bet More with Will Hill - Ep. 134 - Iain...

Shoulda Bet More ·

2025/01/15

With the first round of the NFL Playoffs officially in the books, we look forward to the Divisional round. To give us an early look, we've brought back Iain MacMillan (@IainMacBets) of Sports Illustrated to the pod! We react to the Monday night beatdown by the Rams and what that means for the Vikings going forward. Do they keep Sam Darnold, or is the future JJ McCarthy? With the Chiefs' starters not playing in Week 18, have they rested too long? We look at the matchups for this round and

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34:55

Shoulda Bet More with Will Hill - Ep. 156 - Kiev O'Neil

Shoulda Bet More ·

2025/01/13

Join host Will Hill and returning guest Kiev O'Neil as they break down all the action from NFL's wild-card weekend! From game predictions to big plays, the duo dives deep into what went right, what went wrong, and what they should’ve bet more on. Plus, they look ahead to the high-stakes Monday Night Football matchup and touch on the latest in college football. Whether you're a seasoned bettor or a casual fan, this podcast is packed with insights, analysis, and plenty of laughs. Don’t miss

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30:12

Shoulda Bet More with Will Hill - Ep. 155 - Aaron Schatz

Shoulda Bet More ·

2025/01/10

The NFL Playoffs are finally here. For the next 3 weeks, we have do or die football that culminates in Super Bowl LIX in February. We are gonna get you started off on the right foot this Wild Card Weekend by bringing back on Aaron Schatz of FTN Fantasy. We'll go in-depth on all of the six games that happen this weekend and give you our opinions on the matchup, who is favored, and our favorite bets for each game. Also, because Aaron is a voter for NFL awards, we attempt to pick his brain

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26:15

Shoulda Bet More with Will Hill - Ep. 154 - Brad Powers

Shoulda Bet More ·

2025/01/08

The College Football Playoff Semifinals are this week and we have all the info you need! Brad Powers (@BradPowers7) of the "Bet the Board Podcast" returns so we can do a deep dive into the Orange Bowl between Notre Dame and Penn St. on Thursday, and the Cotton Bowl between Ohio St. and Texas! We look at the lines and give you our favorite plays from the spread, over/under, and player props! We also preview the hypothetical National Championship lines to get an idea of how the books see each

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253 results

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