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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 forward in the series? Who is most likely to win Finals MVP? Also, it sounds as if Dan Hurley might leave UConn for the Lakers. What does it mean for UConn, LeBron, and the Lakers future?

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 deserve a lifetime ban from the MLB? Hear it all on this episode of Shoulda Bet More!

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 well as the MVP award. They look forward to the NBA Finals and give a mini-preview on how they think the series will go. Jeff also goes through who he thinks will surprise this NFL season based on the schedule and teams' offseasons. Plus, will the WNBA do anything about trying to protect Caitlyn Clark after she got shoulder checked against the Chicago Sky?

The NCAA Baseball Tournament begins this weekend! Three weekends of baseball culminating in the College World Series. To get you ready, we've invited, from CollegeBaseballInsiders.com and VSiN, Matt Grissom (@GrissomOnX)! Matt goes over everything you need to know to bet the tournament, his favorites from each regionals, and his favorite bet to win the tournament! Plus, the NBA Finals are set and it will be the Dallas Mavericks facing off against the Boston Celtics. Will give a mini lookahead to see where each team is at before he gives his picks next week!

With the Celtics sweeping the Pacers and reaching the NBA Finals, we thought to bring on Adam Kaufman (@AdamMKaufman) of WRKO 680 in Boston to give us a Boston perspective on sports and betting! Should Boston be concerned about having such an easy path to the Finals? How do they matchup against either the Mavericks or the Timberwolves? What is Adam's Finals prediction? Can the Patriots out-pace their projected win total? Will we see Drake Maye this season or is it Jacoby Brissett's team? How is the Red Sox's season up to this point? Will they surpass their win total? Plus, Will has a baseball future that he believes is the last chance to take! Tune in to find out and beat the books!

Happy Memorial Day! Will invites a new guest, the host of Sunday Bet Prep on VSiN, Dave Ross (@drosssports)! The guys talk everything from MLB, NFL, NBA, UFC, and the PGA Tour! They discuss some of their favorite picks in each sport and how they feel about the various teams and players. Plus, Will goes though some of the baseball games to watch on Memorial Day!