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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. 226 - Drew Dinsick Jun 25, 2025

Show notes

Now that the NBA season is over, we turn our attention to the NBA Draft which already happens tonight! To give a betting preview, we've invited Drew Dinsick (@whale_capper) of NBC Sports back to the pod! We preview the draft beyond just the first couple of picks to get an idea of where draftees will end up so you can know whether to be their over/unders. We also catch up on the trades over the first 2 days of the offseason as we look beyond the draft and towards next season's futures. Who do we like to get out of a wide open East and who do we think is worth a bet to win it all? We discuss that and all the off-season's storylines on today's episode!

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Shoulda Bet More with Will Hill - Ep. 225 - Chris Macero Jun 23, 2025

Show notes

The Oklahoma City Thunder are the NBA Champions after winning in what was an anti-climatic game. To talk about it and more we've brought back professional sports bettor and VSiN contributor, Chris Macero (@RealGadge)! We go over game 7 and talk about Haliburton's injury early in the game and how it shaped the rest of the game. We discuss if the NBA season being too long is what leads to injuries like Haliburton's and if the regular season needs to be shortened. We look towards next season by talking about Kevin Durant's trade to the Rockets and which team will rise out of a wide open Eastern Conference. We also talk about futures and awards bets in baseball as we near the halfway point of the season. Finally, Chris lets us in on his preseason betting process for College Football to give you pointers on how to bet this upcoming season.

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Shoulda Bet More with Will Hill - Ep. 224 - Jonathan Von Tobel Jun 20, 2025

Show notes

It all comes down to one game, Sunday night we will have game 7 between the Pacers and the Thunder. We invite back Jonathan Von Tobel (@meJVT) of VSiN Primetime to discuss how we've ended up here and what we believe will happen in game 7. We recap what we just saw in what was a fairly easy win by the Pacers and what effect does it have on how game 7 will play out. We look at the betting lines for game 7 and discuss if we may see a very tight defensive game that will affect the game total. We look at the MVP market to see if any longshots are worth a bet. Also, with the draft coming up just days after game 7, we look to see the betting markets there and give you our favorite bets. We also try to predict how the offseason will go and how different the league will look next year.

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Shoulda Bet More with Will Hill - Ep. 223 - Jeff Parles Jun 18, 2025

Show notes

Today, we bring back our favorite guest, Jeff Parles (@jeffparles) of "Sports By The Book!" We recap the Stanley Cup Finals as the Florida Panthers become back to back champions. We also recap Game 5 of the NBA Finals. As the Thunder look to win one more to capture the championship, can the Pacers overcome a potential injury to Haliburton? If the Thunder win it all, where do they rank on some of the all-time teams? We talk a little offseason as we try to figure out where Durant and Giannis end up next season, and who will be the next Head Coach for the Knicks? We discuss the baseball season up to this point as well. What are the playoff implications of the Rafael Devers trade? Are the Giants now legit title contenders? What has happened to the New York Yankees as they can't seem to buy a run. We finish off baseball talk with futures and awards markets. Finally will Aaron Rodgers help or hurt the Pittsburgh Steelers this upcoming season?

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Shoulda Bet More with Will Hill - Ep. 222 Jun 16, 2025

Show notes

"Shoulda Bet More" is your go-to sports betting podcast hosted by Will Hill. From NBA buzzer-beaters to MLB home runs and everything in between, Will breaks down the latest action, hottest takes, and sharpest plays across the sports world. Tune in, get the edge, and maybe next time… you shoulda bet more.

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Shoulda Bet More with Will Hill - Ep. 221 - Ben Wilson Jun 13, 2025

Show notes

The College World Series begins today, and we have invited Ben Wilson (@Ben_Wilson_1) from ESPN+, FOX, and VSiN back to the podcast to give us the rundown. We discuss which of the 8 teams has the best path to the National Championship, which team can surprise, and which team we think will win it all. We also go over each of the first round games beginning today for our favorite bets! We also recap and react to Indiana's win in game 3 of the NBA Playoffs. Have they taken control of the series or is it still going to the Thunder's way? Plus, will Giannis stay with the Bucks after all the rumors surrounding him?

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Shoulda Bet More with Will Hill - Ep. 220 - Sammy P Jun 11, 2025

Show notes

With the College World Series upon us on Friday, we bring on Sammy P (@spshoot) of the Chicken Dinner podcast and Fox Sports to give us a preview of the final 8 teams! We go through each of the teams and we give our favorite plays to win it all and discuss the underdogs that are worth a shot. We discuss Fanduel's new 50 cent tax on Illinois better and whether or not it will discourage users from using Fanduel. Will other books begin charging the tax? We also touch on the state of the NBA Finals and the Stanley Cup Finals and talk about our favorite bets that can be placed at this point in the series. We also have US Open preview in golf that you can get some bets in with!

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Shoulda Bet More with Will Hill - Ep. 219 - Ricky G Jun 09, 2025

Show notes

On today's episode we bring in NBA Twitter legend, Ricky G (@jrichardgoodman), to talk the NBA Finals after the Thunder have evened up the series against the Pacers. Is this dominant win the beginning of the end of the series? Will the Pacers be able to conjure up more comeback magic? We preview game 3 and discuss if the Thunder can finally cover on the road in the playoffs. We talk a little offseason to see where we think superstars like Kevin Durant and Giannis Antetokounmpo end up. Also, was Tom Thibodeau's firing by the Knicks deserved? Who is going to replace him? We also talk about the amazing French Open final yesterday and the Red Sox taking 2 of 3 from the Yankees over the weekend.

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Shoulda Bet More with Will Hill - Ep. 218 - Jonathan Von Tobel Jun 06, 2025

Show notes

The Indiana Pacers pull off another playoff comeback! With Tyrese Haliburton hitting a last second shot to put the Pacers up by a point, the Pacers have taken a 1-0 series lead over the Thunder. We have an instant reaction feature Jonathan Von Tobel (@meJVT) of VSiN Primetime as he returns to the podcast! We recap game 1 and detail how the Pacers were able to comeback in the 4th quarter and how they have been doing it all throughout the playoffs. How will this game affect the series going forward? Should the Thunder still be a heavy favorite, or will the books begin to respect the Pacers? Tune in to see how we think the rest of this series goes and how you should bet it!

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Shoulda Bet More with Will Hill - Ep. 217 - Mitch Moss Jun 04, 2025

Show notes

Today, we touch on a little of everything with Mitch Moss (@MitchMossRadio) from VSiN! We talk some baseball and get a snapshot of where we are this season. Is it a viable betting strategy to bet on the Rockies losing? Which division races are the most intriguing this season? Are we going to see Ohtani pitch this season? Which teams do we think will end up making the playoffs in each League? We also touch on where we are at for end of season awards. We recap the wild first weekend in the NCAA Baseball Tournament as well as betting previews for the NBA Finals and the Stanley Cup Finals!

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