The GMs welcome Pittsburgh Pirates manager Derek Shelton to the show. Derek shares his remarkable journey through baseball, from his days as a college catcher and early coaching stints in the minors, to the years he spent grinding as a hitting coach and bench coach across the league. He opens up about the lessons learned along the way, the mentors who shaped his approach, and the challenges of preparing for the opportunity to finally lead a Major League clubhouse. The GM's also discuss the Ryder Cup and rules they would like to see changed in pro sports.

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Jason Garrett joins Rosters to Rings to talk about what makes great leaders and great quarterbacks. From Troy Aikman and Michael Irvin to Dak Prescott and Justin Herbert, Jason shares behind-the-scenes stories and lessons from his years as a player, coach, and broadcaster. Thad, Ryan and Tom also dive into MLB playoff pushes, NFL and NBA roster management, and the always-debated “rest vs rust” dilemma.

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The GM's welcome MLB Hall of Fame Pitcher Greg Maddux to the show. Greg talks about his life on an Army base in Spain where he learned to love sports, the reasons for his tough decision to leave Chicago, and the unwritten rules of hitting and being hit by pitches. Plus, Thad and Ryan break down the latest on Kawhi Leonard and the Clippers, and dive into a candid debate on how far should teams really go to win in pro sports?

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Thad and Ryan welcome ESPN’s Bill Barnwell for a deep dive into the evolution of analytics in sports, especially the NFL. Bill explains how advances in technology and access to game footage have transformed the way he blends data with storytelling in his work. Plus, Ryan unpacks the latest drama in Los Angeles, breaking down the explosive Clippers saga involving Kawhi Leonard and owner Steve Ballmer.

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The GMs welcome former MLB and Team USA catcher and former Seattle Mariners manager Scott Servais, for a candid and wide-ranging conversation. Scott reflects on his unconventional path to the big leagues, breaks down his managerial philosophy across the grind of a full season, discusses his current role with the Padres, and weighs the balance between advanced analytics and gut instinct. Plus, he shares stories from a lifetime of loyalty to the Green Bay Packers.

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Tom Telesco joins Thad to highlight a special episode centered around the big NFL news of the Micah Parson's trade from Dallas to Green Bay. The GMs are joined by Dallas radio personality Jeff "Skin" Wade to not only discuss the trade and to also gauge the reaction of the Dallas fan base to the explosive news.

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Former NFL GM Tom Telesco joins Ryan and Thad to break down the 53-man roster cutdown process, the toughest part of releasing players, and the guys swap swap candid stories about what it’s like when the tables turn, getting cut themselves from their GM roles.

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Ryan is back! Thad and Ryan kick things off by breaking down why NBA franchises are valued higher than MLB clubs, from global reach to media rights. Then they welcome Los Angeles Chargers GM Tom Telesco for a wide-ranging roundtable on what it takes to run a front office in three different leagues.

From his Bill Polian mentorship and the Colts–Patriots rivalry to modern ownership dynamics and risk analysis, Tom shares lessons that translate across all sports. Thad and Ryan close with their take on the MLB trade deadline winners.

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