It has been a wild past few days for MLB Free Agency and to help break it down with Will, we've brought back from "Sports By The Book," Jeff Parles (@jeffparles)! We talk about the shockwaves that are still resonating for Yankee fans after losing Juan Soto to the Mets. Are the Mets now the big brother to the Yankees? How should the Yankees proceed in free agency without Soto? Who is now the favorite to win the American League? Will the Mets be able to displace the Dodgers as the favorites in the National League? We look towards some futures for next season to see if anything is in play. Jeff also gives us his take on the College Football Playoff bracket and tells us his favorite betting looks for the first round and the tournament as a whole. Plus, an early week 15 NFL betting preview!

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

The bracket is set. We now know the 12 teams in the College Football Playoff and we've invited back "The Bear" Chris Fallica (@chrisfallica) from Fox Sports to get an instant reaction. Did the committee get it right? Who got snubbed? Who do we think is going to win it all? We talk about all that and take a look at the first round betting lines to see what angles we like before the lines move. We also give our reactions to Week 14 in the NFL and preview Monday Night Football between the Bengals and Cowboys. Will also discusses Juan Soto's megadeal with the New York Mets and what it means for baseball going forward. 

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

On today's episode of Shoulda Bet More, we invite back Mike Sando (@SandoNFL) of The Athletic to pick his brain on NFL awards. As we draw closer to the end of the season, we talk with Mike to find what he, as a voter, looks for when voting for various awards so we can better understand what voters look for when we place bets on NFL awards. We also talk NFL in general with topics such as his opinion on Week 14's games, whether or not Bryce Young's resurgence is for real, and where will Bill Belichick be coaching next year, if at all? Plus Will recaps Thursday Night Football and gives his favorite bets for Week 14 in the NFL and Conference Championship weekend in College Football!

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Huge weekend of football is coming up. It's conference championship weekend and there is also a fantastic slate of NFL games this week. To prepare you for betting this slate of games, we've brought back from VSiN, Matt Youmans (@mattyoumans247)! We discuss the College Football Playoff rankings and give you their favorite bets to make the playoff in the final week. Could any upsets this weekend change the final 12 teams in the playoff? We look ahead to a great Thursday Night Football matchup between the Packers and the Lions and give you our leans and what we are looking to bet. We also give you our favorite bets for the rest of the weekend so you can get prepared early in the week!

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

On this week’s episode of Shoulda Bet More, He's back! Kiev O'Neil & Will break down the thrilling outcome of Sunday Night Football. Tune in as Kiev gives us his hot takes and analysis on the game’s impact.

We’re also diving deep into the future of college football—what’s next for the sport, the new dynamics, and how upcoming changes might shake things up for players, coaches, and fans alike. Whether you’re a seasoned sports bettor or a casual fan, this episode is packed with insights you won’t want to miss.

Hit play now and let’s talk sports, betting, and everything in between!

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

On this Black Friday edition of Shoulda Bet More, we invite a new guest! From Follow the Money on VSiN, Paul Howard (@paulyhoward)! We recap the Thanksgiving games and discuss the puzzling end to the Bears/Lions game where the Bears go home with a timeout in their pocket. We discuss our favorite bets for the rest of week 13 including today's game between the Raiders and the Chiefs. We also talk the College Football Playoff and whether or not a possible 3 loss team could make the playoff. We also give our favorite College Football picks this weekend and how bad would it be for the Yankees to lose Juan Soto to another team in free agency.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Tomorrow is Thanksgiving and we've got the analysis you need so that while you are stuffing your face with turkey, you are also stuffing your wallet with cash from your bets. To go over every game on Thursday, we've brought back from WKRO 680 and iHeartRadio Boston, Adam Kaufman (@AdamMKaufman)! We give our betting angles for Bears vs. Lions, Giants vs. Cowboys, and Dolphins vs. Packers. Adam also gives us a preview of his favorite bets for the rest of Week 13. Plus we discuss the state of the College Football Playoff and Adam gives us his view on Red Sox free agency!

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Coming off what was a wild NFL Sunday with many games turned on their head, we invite Jeff Parles (@jeffparles) from "Sports By The Book" back to the pod! We recap and react to all the games, many of which had late lead switches and improbable plays. We give you our takeaways for what this week means moving forward in the season. We preview the Har-bowl in tonight's Monday Night Football game between the Ravens and the Chargers. We also discuss the College Football Playoff as the field gets clearer as we head towards the final week of conference play. Who do we think the committee will leave in and out? Plus, we discuss Juan Soto's free agency and how is MLB allowing 2 teams to be playing in Minor League ballparks this upcoming season?

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

On this episode of Shoulda Bet More, we get you ready for Week 12 in the NFL with John Jastremski (@john_jastremski) of The Ringer returning to the pod! We go over our favorite bets for the weekend so you can get the edge on the books. We do a mid-season check on our futures and awards to see how confident we are that they hit. Also, who do we think ends up getting those last playoff spots when the regular season is all said and done? Also, we talk MLB free agency to figure out where the big name free agents like Juan Soto and Roki Saski sign.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Iain MacMillan (@IainMacBets) of Sports Illustrated returns to the pod on this episode of Shoulda Bet More to talk all things NFL. We discuss where we find value on betting division winners this far into the season. Could the Chargers or the Steelers be surprise Super Bowl contenders? What should the Ravens do about a suddenly human Justin Tucker? Why are there so many bad teams in the NFL? Is there a new contender for Offensive Rookie of the Year? We also preview Thursday Night Football to give you our favorite bets and leans as well as our favorite on the Sunday slate of games! Plus, Will recaps and reactions to the award winners for MLB!

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.