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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

00:31:02

Shoulda Bet More with Will Hill - Ep. 241 Dave Ross

Shoulda Bet More ·

2025/09/24

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. 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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00:43:41

Shoulda Bet More with Will Hill - Ep. 240 Jensen Lewis

Shoulda Bet More ·

2025/09/22

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. 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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31:40

Shoulda Bet More with Will Hill - Ep. 229 - "The...

Shoulda Bet More ·

2025/07/02

As we begin July, we've brought back from Fox Sports, "The Bear" Chris Fallica (@chrisfallica) to discuss what's going to be worth betting in the days to come. We talk some MLB to get an idea of where teams and divisions are at the halfway point of the season. Which teams are worth taking at over/under their projected win totals? Will we see any surprise teams in the 2nd half of the season? Which teams are worth taking the market for July wins? We discuss Chris's approach to College

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28:29

Shoulda Bet More with Will Hill - Ep. 228 - Gill...

Shoulda Bet More ·

2025/06/30

To start your week right, we bring back Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod!" We recap this past weekend in baseball to catch you up on what you may have missed. We discuss how the Rafael Devers trade has worked out so far for Gill's Giants. We talk big picture as we approach the halfway point of the season, which team is the best in baseball? Which teams can make a run? Is there any chance that Cal Raleigh takes the AL MVP award from Aaron

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24:05

Shoulda Bet More with Will Hill - Ep. 227

Shoulda Bet More ·

2025/06/27

On today's episode, we recap the NBA Draft. What surprised Will and what he thought of the picks. Also ESPN's coverage of the draft was not good, is there anything that can be done about it? Will also discusses the state of the MLB as we near the midway point of the season. The Yankees have been ceding ground in the AL East. Could they end up losing the division? Do we have a competition for the AL MVP between Cal Raleigh and Aaron Judge? Are there any teams out of the playoff picture right

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35:28

Shoulda Bet More with Will Hill - Ep. 226 - Drew Dinsick

Shoulda Bet More ·

2025/06/25

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

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39:21

Shoulda Bet More with Will Hill - Ep. 225 - Chris Macero

Shoulda Bet More ·

2025/06/23

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

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42:40

Shoulda Bet More with Will Hill - Ep. 224 - Jonathan...

Shoulda Bet More ·

2025/06/20

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

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43:48

Shoulda Bet More with Will Hill - Ep. 223 - Jeff Parles

Shoulda Bet More ·

2025/06/18

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

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30:38

Shoulda Bet More with Will Hill - Ep. 222

Shoulda Bet More ·

2025/06/16

"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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39:08

Shoulda Bet More with Will Hill - Ep. 221 - Ben Wilson

Shoulda Bet More ·

2025/06/13

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

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34:04

Shoulda Bet More with Will Hill - Ep. 220 - Sammy P

Shoulda Bet More ·

2025/06/11

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

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30:16

Shoulda Bet More with Will Hill - Ep. 219 - Ricky G

Shoulda Bet More ·

2025/06/09

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,

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23:52

Shoulda Bet More with Will Hill - Ep. 218 - Jonathan...

Shoulda Bet More ·

2025/06/06

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

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32:03

Shoulda Bet More with Will Hill - Ep. 217 - Mitch Moss

Shoulda Bet More ·

2025/06/04

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

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28:59

Shoulda Bet More with Will Hill - Ep. 216 - Will Hill!

Shoulda Bet More ·

2025/06/02

You read the title right, today is just Will! Will recaps a Game 6 of the ECF that saw the Pacers put away the Knicks and advance to face the Thunder in the NBA Finals. He go over what the Knicks will need to do in the upcoming offseason to try to get over the hump. Will also previews the NBA Finals and is there any chance that the Pacers pull off what may be the upset of a lifetime? Will also talks baseball. He goes over where we are at the start of June in the MLB. He goes over bets that

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32:12

Shoulda Bet More with Will Hill - Ep. 215 - Matt Grissom

Shoulda Bet More ·

2025/05/30

The NCAA Baseball Tournament begins this weekend as start the road to Omaha and the College World Series. To get us ready for the entire tournament, we've brought back Matt Grissom (@GrissomOnX) of CollegeBaseballInsiders.com and VSiN! We go over the College Baseball season to see how we got here and who the favorites are heading into the tournament. We go through the regionals to see who we like to advance to the Super Regionals and if we think any underdogs can advance. We go through some

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29:54

Shoulda Bet More with Will Hill - Ep. 214 - Kelley...

Shoulda Bet More ·

2025/05/28

Both NBA Conference Finals series may nearly be over. With both series being 3-1 in favor of the Thunder and Pacers, we bring Kelley Bydlon (@KelleyBydlon) of VSiN's "A Numbers Game!" to get his opinion on each series. Is there any chance we see each series extended? Are either the Knicks or the Timberwolves worth a bet to come back from these longshot odds? Will the Thunder even lose a game for the rest of this postseason? Tune in to see what we think and to get an edge on the books.

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35:20

Shoulda Bet More with Will Hill - Ep. 213 - Gill...

Shoulda Bet More ·

2025/05/26

On today's episode, we get a snapshot of where we are at in the Conference Finals with Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod!" We go over the Knicks stunning rally against the Pacers as we finally have a series. Do we think the Knicks can take advantage or is this just a speed bump for the Pacers? We also touch on whether or not the Thunder can take a stranglehold on their series against the Timberwolves. We talk a little Tennis with the upcoming

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33:29

Shoulda Bet More with Will Hill - Ep. 212 - Brad Thomas

Shoulda Bet More ·

2025/05/23

Wednesday night had one of the craziest NBA games we've ever seen in Game 1 of the Eastern Conference Final between the Pacers and the Knicks and we have to react to what we saw. To get his opinion on the game and the series moving forward, we invite Brad Thomas (@MrBradThomas) from NBC Sports back to the pod! How were the Pacers able to come back in that game, what did the Knicks do wrong that made them choke their lead? Will the Knicks be able to recover from this game or is it the

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251 results

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