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 spor...
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Nov 13, 2026 · 37:42
On this episode on the Shoulda Bet More podcast Will Hill recaps Thursday night football and gives a best bet for every NFL game. Then Kiev Oneill of the oddsbreakers joins to…
Nov 11, 2026 · 27:11
On this episode of the Shoulda Bet More podcast Will Hill reacts to the Vikings trading for Kirk Cousins, and gives his early thoughts on best bets for the weekend. Then Dave…
Nov 9, 2026 · 33:29
On this episode of the shoulda bet more podcast Will Hill recaps a chalk-filled day in the NFL and Jeff Parles of ESPN Las Vegas joins to react to Bucs/ Bears and discuss the…
Nov 6, 2026 · 37:36
On this episode of the Shoulda Bet More podcast Will Hill previews the week in college and the NFL, reacts to TNF, and Jonathan Von Tobel of Money Moves joins to discuss his best…
Nov 4, 2026 · 34:23
On this episode of the Shoulda Bet More podcast Will Hill discusses the epic College Football slate coming up on Saturday, and reacts to the Justin Herbert trade rumors. Then Tim…
Nov 2, 2026 · 35:06
On this episode of the shoulda bet more podcast Will Hill recaps week 8 of the NFL, and Gill Alexander of A Numbers Game joins to review the day, preview Bears Seahawks and more.…
Oct 30, 2026 · 25:56
On this episode of the Shoulda Bet More podcast Will Hill recaps TNF and breaks down the NFC playoff picture , then gives his thoughts on the NFL and CFB games this weekend…
Oct 28, 2026 · 39:49
On this episode of the Shoulda Bet More podcast Will Hill recaps a wild Rays comeback and Chris Fallica of Fox Sports joins to discuss the CFB slate, the playoff picture , NFL…
Oct 26, 2026 · 43:23
On this episode of the Shoulda Bet More podcast Will Hill recaps the day in the NFL and looks ahead to Mondays games. Then Jeff Parles of ESPN Las Vegas joins to react to the day…
Oct 23, 2026 · 32:49
On this episode of the Shoulda Bet More podcast Will Hill previews the World Series and give his football picks for the weekend . Then Jensen Lewis of vsin by the books joins to…
Oct 19, 2026 · 42:14
On this episode of the Shoulda Bet More podcast Will Hill recaps a wild weekend of football and looks ahead to MNF. Then, Kiev O’Niel of the Oddsbreakers joins to discuss all the…
Oct 16, 2026 · 43:32
On this episode of the shoulda bet more podcast Will Hill reacts to the Brewers sweeping the Dodgers and another OT NFL primetime game. Then Ben Wilson of Fox sports joins to…
Oct 14, 2026 · 40:50
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…
Oct 12, 2026 · 38:07
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…
Oct 9, 2026 · 48:09
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…
Oct 7, 2026 · 36:35
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…
Oct 5, 2026 · 32:05
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…
Oct 2, 2026 · 35:42
On this episode of the Shoulda Bet More podcast Will Hill reacts to the Browns win on Thursday night and previews the divisional round in the mlb playoffs. Then Jeff parles of…
Sep 30, 2026 · 25:57
On this episode of the Shoulda Bet More podcast Will Hill recaps day 1 of the MLB playoff and looks ahead to Wednesdays action. Then, Jensen Lewis of VSIN By the Books joins to…
Sep 28, 2026 · 31:34
In this episode of the Shoulda Bet More podcast, Will Hill is joined by Kiev O’Neil of the Oddsbreakers as they recap all the action we saw in Week 3 of the NFL season and look…
Sep 25, 2026 · 46:04
On this episode of the shoulda bet more podcast Will gives his picks in NFL and college, then Jonathan Von Tobel choice to discuss his best bets in the NFL and a loaded college…
Sep 23, 2026 · 45:56
On this episode of the Shoulda Bet More podcast Will Hill reacts to the Jackson Dart injury and evaluates the Giants options, and gives a preview and best bet for TNF. Then Chris…
Sep 21, 2026 · 39:26
On this episode of the Shoulda Bet More podcast Will Hill reacts to a wild week 2 in the NFL, and Gill Alexander joins to recap the games , preview MNF and look ahead to next…
Sep 18, 2026 · 43:09
On this episode of the shoulda bet more podcast Will Hill gives his NFL week 2 picks , then Jeff parles of espn Las Vegas joins to recap lions Bills and look ahead to week 2 and…
Sep 16, 2026 · 27:59
On this episode of the shoulda been more podcast Will Hill previews Thursday night football between the Lions and Bills with a best bet , and Dave Ross, of VSiN By the Books…
Sep 14, 2026 · 41:41
On this episode of the Shoulda Bet More podcast Will Hill reacts to Week 1 of the NFL and looks ahead to to MNF. Then, Geoff Schwartz of Fox Sports joins to recap the week, look…
Sep 11, 2026 · 39:06
On this episode of the shoulda bet more podcast Will Hill breaks down week 1 of the nfl and reacts to the first 2 games. Then Dustin Swedelson of Cashing out joins to discuss the…
Sep 9, 2026 · 35:07
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 ,…
Sep 7, 2026 · 33:51
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.…
Sep 4, 2026 · 38:02
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…
Sep 2, 2026 · 32:48
On this episode of the Shoulda Bet More podcast Will Hill looks ahead to Week 1 in college football, and Kiev O’Neil of the Oddsbreakers joins to discuss his favorite bets in the…
Aug 31, 2026 · 31:27
On this episode the Shoulda Bet More podcast Will Hill recaps week 0 in college football and looks ahead to Week 1. Then Brad Thomas of CBS Sports joins to review week 0, and…
Aug 28, 2026 · 35:46
On this episode of the Shoulda Bet More podcast, Will Hill breaks down week 0 of the college football season, and Stormy Buonantony of Money Moves and ESPN joins to discuss her…
Aug 26, 2026 · 35:01
On this episode of the Shoulda Bet More podcast Will Hill talks Week 0 in college football, then Dave Ross of VSiN By The Books joins to discuss his NFL thoughts, mlb races, and…
Aug 24, 2026 · 42:33
On this episode of the Shoulda Bet More podcast, Will Hill recaps week 2 of the preseason, and Chris "The Bear" Fallica of Fox Sports joins to discuss his best bets in college…
Aug 21, 2026 · 33:01
On this episode of the Shoulda Bet More podcast, Will Hill looks at the weekend in MLB, then Gill Alexander of A Numbers Game joins to discuss his process prepping for football…
Aug 19, 2026 · 32:29
On this episode of the Shoulda Bet More podcast, Will Hill discusses Max Fried’s injury and its impact on the Yankees' futures prices. Then, Jensen Lewis of Vsin By The Books…
Aug 17, 2026 · 36:50
On this episode of the shoulda bet more podcast, Will Hill takes a look at the MLB races and reacts to the first of the NFL preseason. Then Brett Ciancia of Pick Six Previews…
Aug 14, 2026 · 36:31
On this episode of the Shoulda Bet More podcast, Will Hill gives out some MLB Futures, and then Mike Sando of the Athletic joins to discuss his annual NFL QB Tiers column. Hosted…
Aug 12, 2026 · 38:44
On this episode of the shoulda bet more podcast, Will Hill breaks down week 1 of the NFL preseason, then Jeff Parles of ESPN Las Vegas joins to discuss the NFL season, sleeper…
Aug 10, 2026 · 35:03
On this episode of the Shoulda Bet More podcast. Will Hill breaks down the MLB races, including some best bets. Then John Jastremski of SNY joins to discuss MLB futures, division…
Aug 5, 2026 · 25:13
On this episode of the shoulda bet more podcast, Will Hill and Brad Powers preview the college football season, with a look at futures, win totals, early-season games, and more…
Aug 3, 2026 · 42:52
On this episode of The Shoulda Bet More podcast, Will Hill breaks down the latest in Major League Baseball, including the huge trade of Tarik Skubal to the Dodgers, and some of…
Jul 31, 2026 · 35:46
On this episode of The Shoulda Bet More podcast Will Hill gives his thoughts on the MLB trade deadline and pennant races with a best bet. Then Kiev O'Niel of the Oddsbreakers…
Jul 29, 2026 · 34:09
On this episode of the Shoulda Bet More podcast, Will Hill gives out a long shot MLB award bet. Plus, Steve Fezzik joins to discuss prediction markets, the NFL preseason and win…
Jul 27, 2026 · 42:54
On this episode of the Shoulda Bet More podcast, Will Hill breaks down LeBron James taking his talents to the Philadelphia 76ers, how he'll impact the team and how the move…
Jul 24, 2026 · 37:59
On this episode of the Shoulda Bet More podcast, Will Hill welcomes VSiN's Dustin Swedelson to discuss his favorite NFL bets, the MLB Trade Deadline, and go head-to-head in…
Jul 22, 2026 · 35:46
On this episode of the Shoulda Bet More Podcast, Will Hill gives out some AL longshot futures and shares his thoughts on NL MVP. Plus, Jensen Lewis, VSiN By The Books Host and…
Jul 20, 2026 · 44:16
On this episode of the Shoulda Bet More podcast, Will Hill takes a look at some early odds and storylines around college football before chatting some storylines happening in the…
Jul 17, 2026 · 30:12
On this episode of the Shoulda Bet More podcast, Will Hill previews the World Cup Final and looks ahead to the 2nd half of the MLB season. Plus, Sammy P from Fox Sports joins to…
Jul 15, 2026 · 22:59
On this episode of the Shoulda Bet More podcast, Will Hill reacts to the home run derby and previews the World Cup Semifinal between England-Argentina. Plus, Jeff Parles from…
Jul 13, 2026 · 42:45
On this episode of the Shoulda Bet More podcast, Will Hill takes a look around Major League Baseball heading into the break, as well as the Home Run Derby and All-Star game. Also…
Jul 10, 2026 · 27:02
On this episode of the Shoulda Bet More podcast, Will Hill looks at an overview of the MLB season entering all star weekend, then Brad Thomas of CBS Sports joins to preview the…
Jul 8, 2026 · 26:01
On this episode of the Shoulda Bet More podcast, Will Hill previews the Wednesday MLB games, including a best bet. Then Julian Edlow of DraftKings joins to discuss the nba summer…
Jul 6, 2026 · 44:42
On this episode of Shoulda Bet More, Will Hill chats the World Cup and the latest headlines around Major League Baseball. Also on the show, Chris Fallica from FOX Sports and the…
Jul 3, 2026 · 31:38
On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Jaylen Brown trade and discusses the struggling Yankees. Then, Mitch Moss of Follow the Money joins to…
Jul 1, 2026 · 30:57
On this episode of the Shoulda Bet More podcast, Will Hill breaks down the U.S. Soccer matchup Wednesday and LeBron James leaving the Lakers. Then, Jeff Parles of ESPN Las Vegas…
Jun 29, 2026 · 44:42
On this episode of Shoulda Bet More, Will Hill reacts to the World Cup and the latest headlines around Major League Baseball. Also on the show, VSiN contributor and "New York,…
Jun 26, 2026 · 30:40
On this episode the Shoulda Bet More Podcast , Will Hill reacts to the NBA Draft and recent blockbuster trades. Plus, Will is joined by MLB Network Host and former Mets GM Steve…
Jun 23, 2026 · 26:57
On this episode the Shoulda Bet More podcast Will Hill gives his finals thoughts on the NBA Draft. Then, expert draft bettor Luke Swain (Vegas Refund) joins to give out best bets…
Jun 22, 2026 · 44:42
On this episode of the Shoulda Bet More podcast, Will Hill gives his take on the NBA Draft and some ways to bet the futures market. Also on the show, VSiN's A Numbers Game…
Jun 19, 2026 · 33:40
On this episode of the Shoulda Bet More podcast, Will Hill gives his take on when and where Giannis will get traded. Then, Dave Ross of VSIN By The Books joins to discuss the…
Jun 17, 2026 · 38:03
On this episode of the Shoulda Bet More podcast, Will Hill looks ahead to the NBA Draft and gives a long shot NFL Award bet. Then, from Fox Sports is Geoff Schwartz, former NFL…
Jun 15, 2026 · 44:42
On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Knicks winning the NBA Finals and whether or not the Spurs blew it on the way. Also on the show, Chris…
Jun 12, 2026 · 30:49
On this episode of the Shoulda Bet More podcast, Will Hill reacts to an epic Game 4 of the NBA Finals and the Knicks making a historic comeback against the Spurs, then what to…
Jun 10, 2026 · 33:00
On this episode of the Shoulda Bet More podcast, Will Hill reacts to Game 3 of the NBA Finals and looks ahead to Game 4. Plus, Kelley Bydlon from a A Numbers Game joins to…
Jun 8, 2026 · 44:42
On this episode of the Shoulda Bet More podcast, Will Hill recaps the Knicks taking a 2-0 series lead in the NBA Finals and if the Spurs have any chance at making a comeback, as…
Jun 5, 2026 · 30:29
On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Knicks Game 1 victory in the NBA Finals and looks ahead to Game 2. Then, Jonathan Von Tobel of Money…
Jun 3, 2026 · 39:11
On this episode of the Shoulda Bet More podcast, Will Hill gives his thoughts on the NBA Finals and the Aaron Judge injury’s impact on the AL MVP race. Then, pro sports bettor…
Jun 1, 2026 · 44:42
On this episode of the Shoulda Bet More podcast, Will Hill previews the NBA Finals between the Spurs and Knicks and some trends and numbers around the series. Also on the show,…
May 29, 2026 · 31:14
On this episode of the Shoulda Bet More podcast, Will Hill reacts to another blowout in the Western Conference Finals, and then Gill Alexander of A Numbers Game joins to preview…
May 27, 2026 · 28:40
On this episode the Shoulda Bet More podcast, Will Hill reacts to the Knicks making the NBA Finals and discusses their chance in the NBA Finals. Then, Jensen Lewis of ESPN and…
May 25, 2026 · 44:42
On this episode of the Shoulda Bet More podcast, Will Hill previews the NBA Conference Finals and if the Knicks have a shot at winning it all. Also on the show, sports betting…
May 22, 2026 · 34:27
On this episode of the Shoulda Bet More podcast, Will Hill previews Game 3 of Spurs / Thunder and shares his thoughts on some MLB storylines entering the weekend. Then, Brad…
May 20, 2026 · 32:19
On this episode of the Shoulda Bet More podcast, Will Hill previews Game 2 of Spurs / Thunder and relives a classic Game 1. Then, Jonathan Von Tobel of Money Moves joins to…
May 18, 2026 · 45:06
On this episode of the Shoulda Bet More podcast, Will Hill previews the Conference Finals for the NBA playoffs, including the Spurs chances against the Thunder and if the Knicks…
May 15, 2026 · 39:37
On this episode of the Shoulda Bet More podcast, Will Hill previews both Game 6s in the NBA, then pro sports bettor Steve Fezzik joins to discuss the NFL schedule release, NBA…
May 13, 2026 · 42:16
On this episode of the Shoulda Bet More podcast, Will Hill looks at the Cavs - Pistons series and gives a best bet for Game 5, and discusses the NBA offseason. Then, Dave Ross of…
May 11, 2026 · 44:42
Will Hill is joined by Gill Alexander to break down several major betting storylines across the sports world. The guys preview key NBA Playoff matchups including Thunder at…
May 8, 2026 · 31:58
On this episode of the Shoulda Bet More podcast, Will Hill previews the Friday night NBA games and recaps the Pistons victory over the Cavs. Then, Mitch Moss of Follow The Money…
May 6, 2026 · 34:44
On this episode of the Shoulda Bet More podcast, Will Hill previews Game 2 of Sixers/Knicks and Wolves/Spurs, the AL Cy Young, and the passing of John Sterling. Then, Sammy P of…
May 4, 2026 · 34:51
On this episode of the Shoulda Bet More podcast, Will Hill reacts to the weekend of action in the NBA, then Jonathan Von Tobel of Money Moves joins to look ahead to Round 2 of…
May 1, 2026 · 29:58
In this episode of the Shoulda Bet More podcast, Will Hill previews Friday's NBA games. Plus, Chris Macero, Professional Sports Bettor joins to break down the Kentucky Derby, NBA…
Apr 29, 2026 · 27:32
On this episode of the Shoulda Bet More podcast, Will Hill recaps the night in the NBA and looks ahead to Wednesday and Thursday action. Then “the Bear” Chris Fallica of Fox…
Apr 27, 2026 · 47:00
On this episode of the Shoulda Bet More podcast, Will Hill recaps this weekend's NBA Playoff games and looks ahead to Monday's games. Plus, Will shares his takeaways from the NFL…
Apr 24, 2026 · 28:11
On this episode of the Shoulda Bet More podcast, Will Hill recaps a wild first round of the NFL draft and analyzes some of the surprising picks, and recaps the night in the NBA…
Apr 22, 2026 · 42:09
On this episode of the Shoulda Bet More podcast, Will Hill previews the Wednesday NBA Playoff action and the NFL Draft. Then, Jeff Parles of ESPN Las Vegas joins to discuss the…
Apr 20, 2026 · 48:06
On this episode of the Shoulda Bet More podcast, Will Hill reacts to the opening weekend of the NBA Playoffs and gives his thoughts on the Giants / Bengals trade. Plus, Geoff…
Apr 17, 2026 · 32:38
On this episode of the Shoulda Bet More podcast, Will Hill previews the two remaining NBA Play-In games and discussed all six playoff series that are set. Then, Jonathan Von…
Apr 14, 2026 · 38:37
On this episode of the Shoulda Bet More podcast Will Hill gives his best bets on the Play-In games, then Kelley Bydlon of A Numbers Game joins to break down the NBA…
Apr 13, 2026 · 47:02
On this episode of the Shoulda Bet More podcast, Will Hill recaps a wild Masters tournament and gives his thoughts on the NBA Play-In Games and the weekend in MLB. Then Gill…
Apr 10, 2026 · 40:00
On this episode of the Shoulda Bet More podcast, Will Hill recaps the first round of The Masters and reacts to Joel Embiid news ahead of the last weekend of the NBA regular…
Apr 8, 2026 · 40:49
On this episode of the Shoulda Bet More podcast, Will Hill reacts to Michigan defeating UConn and looks at next year's odds. Then, “The Bear” Chris Fallica from FoxSports joins…
Apr 6, 2026 · 39:04
On this episode of Shoulda Bet More , Will Hill previews UConn-Michigan and gives a long shot bet for AL MVP. Plus, Matt Youmans from VSIN joins the show to discuss the National…
Apr 3, 2026 · 30:19
On this episode of the Shoulda Bet More podcast, Will Hill previews the two Final Four matchups and gives his best bets. Then, pro bettor Steve Fezzik joins to discuss his…
Apr 1, 2026 · 38:44
On this episode of the Shoulda Bet More podcast, Will Hill takes a look at Most Outstanding Player odds for March Madness and discusses the Final 4 matchups. Then, Ian Eagle of…
Mar 30, 2026 · 42:48
On this episode of the Shoulda Bet More Podcast, Will Hill reacts to a classic UConn - Duke game in the Elite Eight. Plus, Jonathan Von Tobel from Money Moves joins the show to…
Mar 26, 2026 · 45:39
On this episode of the Shoulda Bet More podcast, Will Hill previews the Sweet 16 games for Friday. Then Jeff Parles of ESPN Las Vegas joins to break down Friday's college…
Mar 25, 2026 · 40:15
On this episode of the Shoulda Bet More podcast, Will Hill gives his best bets for the Sweet Sixteen, and previews MLB Opening Day. Then, Mitch Moss of Follow the Money joins to…
Mar 23, 2026 · 26:02
On this episode of the Shoulda Bet More podcast, Will Hill is joined by Gill Alexander of A Numbers Game to recap the weekend in college hoops, look ahead to the sweet 16, and…
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