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!

It's Memorial Day weekend and to get you guys some great picks heading into the long weekend, Will has invited from "Follow the Money" on VSiN, Mitch Moss (@MitchMossRadio)! The guys talk a ton of baseball including which longshots can possibly sneak their way the Cy Young award in each league, the threat level of the division leaders and some of those in wild card slots, and longshots to win the World Series. Are the Timberwolves in any trouble after game one now that Dallas is favored in the series? How does Boston match up against either of these teams? We get Mitch's take on his bets for the NFL season now that he's seen the schedule. Plus, NHL bets: who wins the Stanley cup and who wins the Conn Smythe Award?

Joining Will on the pod for this episode, from VSiN and the Double Play Podcast on the DraftKings Network, Dustin Swedelson! We are just about two months into the baseball season, so how do the guys think the rest of the season is going to shake out? We get their takes on some of the competing teams. Dustin also has some end of season awards bets and a World Series future he really likes. A preview on the Timberwolves/Mavericks series, a Knicks post-mortem and offseason lookahead, and one team that Dustin is going all-in on this upcoming NFL season. Tune in to find out!

What. Just. Happened? Coming directly off the heels of the Nuggets blowing a 20 point lead against the Timberwolves in game 7, Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" returns to the podcast with Will to give their raw reactions to what we all just witnessed. They also talk about how the Pacers took care of the Kicks in MSG in that game 7. An early look at the upcoming Conference Finals series and some betting looks that intrigue the guys. We also get Gill's season long NFL bet that he's locking in after the schedule release. Plus a look at the bets teams in MLB this year and whether or not they can keep it up until October.

One of our favorite guests, Jonathan Von Tobel (@meJVT) of VSiN Primetime returns to the pod to talk NBA Playoffs and NFL Futures after the release of the schedule! After the Timberwolves blew out the Nuggets in game 6, we get the best words in sports: game 7. Will and JVT talk about how we ended up here and who they feel will come out on top and why after what has been a crazy back and forth series. They also talk about whether or not the Knicks can close out their series on the road and what the best bet is for that game. Plus, futures bets that may be affected by how the schedule shook out for some teams. Tune in to get a leg up on the books!

From NBC Sports and GoldBoys, Brad Thomas (@MrBradThomas) joins will to talk a number of sports on the pod. Will and Brad talk break down each NBA Playoffs series from an analytical and betting perspective, giving you some picks they like for individual games and each series as a whole. They also go over the upcoming PGA Championship, where Brad gives some of his favorite looks and why it might not be such a walk in the park for Scottie Scheffler. Plus, some NFL and College Football futures looks from Brad!

From Pregame.com, Scott Seidenberg joins the podcast to talk all things NBA, NFL, NHL, and MLB with Will! How have the Nuggets got themselves back into this series with Minnesota and will they end up winning the series? Will Tom Thibodeau playing his players too long be the reason the Knicks potentially lose the series to the Pacers? Can the Cavaliers put up any fight against the Celtics? Who ends up advancing from the Mavericks/Thunder series? Scott gives his predictions for the rest of the Stanley Cup Playoffs and even gives out his favorite bet for the Conn Smythe award. Why does the media disrespect the New York Jets coming into this season? Finally, what do the Yankees need to take the AL East and the World Series this year. It's a jampacked episode, so tune in to get your sports and betting fix!

NFL Senior Writer for The Athletic, Mike Sando (@SandoNFL) returns to the podcast to chat NFL with Will! In it, they talk about which teams have had a good or bad offseason after we've had some time to process the draft. They also talk about the QB tier list and which QBs they expect to rise and fall in the upcoming season, and will the Chargers be immediately competitive with the hiring of Jim Harbaugh? Also, The Knicks win game 2, but can they win in Indiana with their mounting injuries? The Cavs upset the Celtics in game 1, what does that mean for the series moving forward? Plus, Will gives some of his best bet looks for today's games. Tune in to find out!

On today's episode, NicLarson (@NicLarsonGB) from GoldBoys stops by to talk the ongoing NBA Playoffs and the MLB season so far. He talks about his day to day betting process and how he looks for the lines that he likes, looks for each league's Cy Young award at this point, and some stories about working in a AA clubhouse back in the day with some soon to be major leaguers. Also, can Denver fight their way out of a 0-2 hole on the road? Takeaways from a poorly officiated game 1 in the Knicks/Pacers series and a bonus review of the Roast of Tom Brady!

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!

It's Derby time! The Kentucky Derby is tomorrow and to give his take on the race, Drew Dinsick (@whale_capper) of NBC Sports joins the pod with Will. The guys talk about how to bet the Derby, whether it's worth it to take the favorite, and the horses that may surprise. They also go over their plays for the NBA Playoff games today and a preview of the 2nd round along with some of their plays for those series. Don't miss out on the chance to bet these plays by tuning in!

In this episode of Shoulda Bet More, Brandon Anderson (@wheatonbrando) from Action Network joins the show to talk some NBA playoffs and some post-draft NFL. The Knicks were unable to close out their series last night, should they be worried going into game 6? The guys go through each of the still ongoing series and give their best bets on the each series and some props to play on the upcoming games. They also look ahead to the confirmed matchups in the next round and give their takes on the matchups. And finally, who are some of the teams to be looking at for futures plays post NFL draft and did the Vikings make the right call with JJ McCarthy as their future QB?

The NFL Draft is complete. The NBA Playoffs continue. Raheem Palmer from The Ringer (@iamrahstradamus) joins Will on this episode of the Shoulda Bet More podcast. Can the Sixers rally back against the Knicks? Can the Mavericks take down the Clippers? Is Lebron able to carry the Lakers to be the first team in the NBA to come back from being down three? Will the Cavs turn it around after losing two in a row? What two teams make it to the finals? What superstars will move this offseason? Tune in to hear what all these two have to share!

Night one of the NFL Draft is in the books and boy was it chaotic. Here to recap and react to everything we just saw is Will and Matkafee (@matkafee) from GoldBoys. What did the guys think of the Michael Penix Jr. pick by the Falcons? What other surprises were there on night one? Who are the booms and busts from the first round? Plus, very early Offensive/Defensive Rookie of the Year betting looks! The guys also talk about some of their Friday NBA looks plus a look at each series and whether or not the team down in the series can mount a comeback. Tune in to get some of the best betting looks you can find on any podcast!

The NFL Draft is tomorrow and we are excited and ready to see who goes where! In this episode of Shoulda Bet More, Fred Segal of Freezing Cold Takes (@OldTakesExposed) comes on to talk about his new book, "Freezing Cold Takes: NFL: Football Media’s Most Inaccurate Predictions—and the Fascinating Stories Behind Them." They talk about the origin of the famous account, some of the NFL Draft's most freezing cold takes as well as some of the most freezing cold takes of all time! Plus, Will gives his mock top 10 picks and his Wednesday/Thursday picks for the NBA Playoffs!

The NBA Playoffs have started and to talk what happened over the weekend, Kelley Bydlon (@KelleyBydlon) from VSiN's "A Numbers Game" returns to the pod! Will and Kelley talk about each series and what they've learned from the first batch of games. What would winning and losing mean to the teams in the playoffs? Which team has the best chance to upset the possible Nuggets/Celtics final? Plus, the guys talk the NFL Draft and talk about the possible draft order for the first couple of picks. Also, Will has a play he really likes for one of the Monday night playoff games! Tune in to get a leg up on your bets!

In the final episode before a mini break for the show, Will brings on Aaron Schatz of FTN Fantasy to talk the NFL offseason and the upcoming draft! The creator of DVOA goes over what teams he thinks have had good and bad offseason so far, where the rookie QBs may land, and what his models think various teams' win totals will be! Will also gives out some NFL draft looks for various teams that you may want to consider betting. Tune in to hear those bets and the opinions on the league that may help you to beat the books!