Shoulda Bet More

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

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 Bree

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

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 C

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 o

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 ab

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 Final

Game 1 of the NBA Finals is in the books, and what a dominant win by the Boston Celtics. Kelley Bydlon (@KelleyBydlon) from VSiN's "A Numbers Game" joins Will as he returns to the pod to get an instant reaction to what we saw and what it means for the rest of the series. What does Dallas need to do to win in game 2. How does the outcome of game 1 change betting strategies moving fo

Joining Will on this episode of Shoulda Bet More is Jason McIntyre (@jasonrmcintyre) from The Straight Fire podcast and The Herd! The two share what they're looking at as the NBA Finals approach. Should the Mavericks be the favorites to win it all? Should Angel Reese receive credit for the popularity of the WNBA or should all the credit go to Caitlin Clark? Does Tucupita Marcano de

Joining Will on the pod today is one of our favorite guests, from Sports by the Book, Jeff Parles (@jeffparles)! They talk about the takeaways from each division in baseball two months into the season. Who they think are making the postseason and who will be on the outside looking in. They also discuss who will win and who is worth betting on the Cy Young award for each league as w