On this episode of Shoulda Bet More, Andy McCollough, Senior Writer (@ByMcCullough) for The Athletic, comes onto the pod to talk about his new book, "The Last of His Kind," a biography of Clayton Kershaw. We get a little preview about some of the topics in the book such as talks about his regular season success vs. his postseason struggles and him and the Dodgers finally winning the World Series in 2020. Andy also gives some of his thoughts on the MVP race and who he thinks is built to win the World Series this year. Plus, Will goes over the final weekend of round 1 of the NBA Playoffs and the Timberwolves game 1 win against the Nuggets in round 2. Also some of the bets bets for the round 2 series coming up!