Shoulda Bet More

He's back! To discuss what has suddenly become some very competitive MLB division races, Jeff Parles (@jeffparles) returns to the pod! We talk about how the Phillies and Dodgers have let the teams below them slowly creep up to first place, so which team is more likely to blow the division? We get Jeff's opinion on the AL East race between the Yankees and the Orioles with the trade deadline wrapped...

Now that we've had time to digest what's happened at the trade deadline, we've brought on from SNY and the "New York, New York" podcast on the Ringer, John Jastremski (@john_jastremski)! We go over what the Yankees and Mets did at the deadline and was it enough for either team? We look at the rest of the league and try to predict the division races from here on out as well as which teams will take...

Dive into the latest edition of "Shoulda Bet More" as we sit down with Hitman from TheHammerHQ! 🏈💰 Get ready for a thrilling discussion packed with insider knowledge and expert predictions on the NFL preseason. Whether you’re a seasoned bettor or just starting out, Hitman’s insights are a game-changer. All this action is brought to you by the Gold Boys Network. Don’t miss out—hit that play butto...

We continue our series of College Football and NFL previews with Brad Thomas (@MrBradThomas) from NBC Sports and GoldBoys! Brad gives us his overrated and underrated teams in both College Football and the NFL. As an SEC guy, Brad gives us his takes on Alabama, Ole Miss, and Texas in their first year in the SEC. Also as an extra bonus, we get tips on betting the Olympics! Plus, Will goes over some...

We are less than a week from the Hall of Fame game in Canton to kickoff the NFL Preseason. To get another perspective of how the season will turn out, we've brought back the father of DVOA, Aaron Schatz of FTN Fantasy. Aaron lets us in on what the advanced stats for the upcoming season say about what various teams' strengths and weaknesses are, where teams will place in their divisions, and how th...

We have the awards guru from VSiN, Femi Abebefe (@FemiAbebefe) on today's episode of Shoulda Bet More! In baseball, we talk about the race for the AL MVP, AL/NL Cy Young, and Femi gives us a World Series exacta that he loves the value in! In football, we get his takes on who will end up being the worst team in the league, and who will surprise which may trigger a coach of the year bet. We also get...

We can almost say football is back! NFL Teams report to training camps this week and to talk about his experience and his opinions on the upcoming season, we've brought on former NFL Offensive Lineman and from Fox Sports, Geoff Schwartz (@geoffschwartz)! Geoff discusses how he handicaps games based on offensive line play from what he knows from his playing days. We also get his opinions on teams h...

The second half of the MLB season begins today! For more preview of how the second half will play out, we've brought back Adnan Virk (@adnansvirk) from MLB Network and the Cinephile with Adnan Virk podcast! We talk about the AL East, is it a two team race between the Orioles and the Yankees, or can the Red Sox continue their hot streak and compete for the division? We discuss the trade deadline, w...

With the All-Star Game now behind us, we look forward to the 2nd half of the MLB season. To get us started, we've invited Dave Ross (@drosssports) from Sunday Bet Prep on VSiN back to the podcast! When he was on last, his Mets were in the gutter. Now, they have brought themselves back to looking like a potential playoff team! We talk about what they will do at the upcoming trade deadline and wheth...

On this episode of Shoulda Bet More with Will Hill we dive deep with our special guest, Kiev O'Neil from The Odds Breakers (@OBKiev). He's back! and brings his sports-betting expertise to the table as we discuss the hottest topics in the gambling universe. Tune in as Kiev joins us for an engaging discussion on NFL schedules, the MLB All-Star break, and the thrill of college football. Get ready to...

One of our favorite guests, Jonathan Von Tobel (@meJVT) of VSiN Primetime returns to the pod! We discuss NBA Summer League and how to bet it. We talk about the upcoming NBA season and any pre-season award betting looks. As we are a little bit more than a month out of football season starting, we talk about overrated/underrated college football teams of the Big 12 and Mountain West conferences. We...

As we get deeper into the summer season, fall creeps ever closer. Which means football is coming up soon! To talk about all things football as well as NBA Summer League, and baseball, we've brought back Julian Edlow (@julianedlow) from the DraftKings Network! Julian gives us his NFL wins over/under takes and his thoughts on some player prop bets that he likes. We also get a College Football Week 1...

The Bronx is burning! The Yankees have been struggling for the past month and to talk about their struggles, we've brought back "The Bear" Chris Fallica (@chrisfallica) from Fox Sports! Will and Chris discuss how the Yankees have got to this point, whether or not they can hold on to a playoff spot, and what needs to be done for them to right the ship. They also talk about the upcoming college foot...

One of our favorite guests, from Sports by the Book, Jeff Parles (@jeffparles) is back! Will and Jeff talk about how Jeff's Mets is having a post Grimace-First-Pitch resurgence. Is it worth a bet on them to make the postseason with the run they've been making? On the other side of the city, the Yankees have struggled. What do they need to do to keep pace with the Orioles to try to win the AL East?...

On this episode of Shoulda Bet More, Reed Wallach (@ReedWallach) of The Early Reed Podcast and Sports Illustrated swings by to give his thoughts on NBA Free Agency and College Football! We discuss the Free Agency moves that have been made and which teams are best situated coming into the season to win the NBA Finals. With College Football coming up in a little over a month, we go over how teams wi...

July has begun which means it's time for Wimbledon. To talk some lawn tennis, we've brought back Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod." Gill gives us some of his analysis of the men's and women's tournament that lead to the bets he likes for the first round of the tournament all the way to the finals. Gill also gives us his football hot takes for the u...

As summer starts, football draws ever closer. On this episode of Shoulda Bet More, we've invited Brad Powers (@BradPowers7) of the Bet The Board Podcast onto the pod to give us his analysis on this upcoming season of College Football. In it we discuss the overrated and underrated teams of the upcoming season, over/under on win totals, Heisman Trophy bets, National Championship bets, week 0 and 1 b...

Now that we are officially in the NBA offseason, it's time for the NBA Draft. To give his analysis and predictions, we've invited Drew Dinsick (@whale_capper) of NBC Sports back onto the podcast. We get his thoughts on who the first 6 picks will be, what the Hawks should do with the number 1 pick, where Zach Edey will end up in the draft, and what he thinks will happen this offseason when it comes...

The best two words in sports...Game Seven. Tonight, the Stanley Cup Winner is decided between the Edmonton Oilers and the Florida Panthers. To give the best insight on the game tonight, we've invited Alex B Smith (@axmithsports) of The Ice Guys to the pod to give his best bets and leans. We talk about how the series has gotten to this point as it looked like the Panthers were going to coast to a c...

Will is joined by Adam Chernoff (@adamchernoff) on this episode of the Shoulda Bet More podcast. The two touch briefly on the NHL Stanley Cup Finals before diving deep into the upcoming NFL season. Can the Oilers force a game seven against the Panthers. Adam shares some of his controversial takes for the upcoming season. Will the Carolina Panthers be a wildcard contender? Will Breece Hall win Offe...

We are nearing the end of June, so we've brought Jason Weingarten (@Spreadapedia) from VSiN back to the pod to talk some baseball. We get his takeaways on the division races and end of season awards such as league MVPs, Cy Youngs, and Rookies of the Year. Where those bets stand, who he likes, and who he's keeping an eye on who may not be a favorite right now! Plus, the Celtics have won the NBA Fin...

Scott Seidenberg (@ScottsOnAir) from Pregame.com returns to the pod as we get his takes on the NBA Finals, Stanley Cup Finals, and on the MLB season! With both the NBA and the NHL's Finals mirroring each other, do we see both series get extended to a game 6? Will Jaylen Brown or Jason Tatum win Finals MVP if the Celtics close it out? Is there any chance Connor McDavid can win the Conn Smythe Award...

We are down to 8 teams and the College World Series officially starts today! We've brought back from CollegeBaseballInsiders.com and VSiN, Matt Grissom (@GrissomOnX) to get an update on what we've seen so far in the tournament, and to get his thoughts and predictions on the 8 teams remaining! We get Matt's best bets on each matchup in the first round, plus who he thinks will come out of each brack...

As the NBA and Stanley Cup Finals keep going on, Ben Wilson (@Ben_Wilson_1) from ESPN+, FOX, and VSiN joins the podcast to give his perspective on how each series is going! Ben and Will discuss which team has a better chance of climbing out of their 0-2 deficit, the Mavericks or the Oilers. Ben and Will give their bets and predictions for how each series will end. They also talk about the upcoming...

The Celtics have taken a commanding 2-0 lead in the NBA Finals. To discuss how the Celtics are doing it, we've brought Jonathan Von Tobel (@meJVT) of VSiN Primetime back to the pod! Will and JVT go over what the Celtics have done right, what the Mavericks have done wrong, and what the Mavericks can do to get back into this series. Jayson Tatum is currently the favorite to win Finals MVP, but is th...