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Rosters to Rings Podcast

Rosters to Rings Podcast

By: The 8 Side
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About this listen

Welcome to the Rosters to Rings Podcast where General Managers from the MLB, NBA, NFL and more will take you behind the curtain and share their unfiltered experiences and evaluations of past and present events in professional sports.

Due to competitive reasons, league rules, ownership directives and extreme discretion, General Managers share approximately 40% of what they know and experience with fans. At the Rosters to Rings Podcast, we are here to share as much of the other 60% as we can. We will dive deep into not only what decisions are made, but how and why they are made, the strategic nature of negotiations, roster construction, the characters that make up the game, and the true depth of relationships between executives, coaches, players, agents, media and fans.

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Episodes
  • The Deals You Make and Don’t Make with Mariners GM Jerry Dipoto
    Apr 23 2026

    In Part 2 with Jerry Dipoto, Thad and Jerry discuss his rise from interim GM to leading the Los Angeles Angels, the difficult decision to step away, and how that path led him to the Seattle Mariners. Jerry shares what it takes to take over a franchise, the early days of building in Seattle, the trades you make and the many you don't, and the bold deal for Luis Castillo in 2022 that helped shape one of baseball's best pitching staffs.

    Plus, Thad and Producer Jason break down the Mets’ losing streak, how GMs handle media chaos, and the record $3.9 billion sale of the Padres.

    See omnystudio.com/listener for privacy information.

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    55 mins
  • Giannis, Tanking and Playoff Pressure with Tommy Sheppard
    Apr 16 2026

    Former NBA GM Tommy Sheppard joins the show to break down the evolving situation with the Milwaukee Bucks, the realities of tanking and the pressure facing contenders this postseason.

    Plus, a full NBA Playoff preview including upset watch teams, breakout candidates, and the matchups that could define this year’s run.

    See omnystudio.com/listener for privacy information.

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    58 mins
  • A Life in Baseball with Mariners GM Jerry Dipoto
    Apr 9 2026

    Thad sits down with longtime colleague and Seattle Mariners GM Jerry Dipoto for Part 1 of a wide-ranging conversation on his journey through the game.

    Before becoming one of baseball’s most active front office leaders, Dipoto was a big leaguer with a deep understanding of the game from the clubhouse. He shares his sports origin story, experiences as both a pitcher and switch hitter, and what it was like navigating the realities of being traded as a player - insights that now shape how he operates as a general manager.

    Jerry also reflects on playing alongside and learning from legends of the game, including Jack Morris, Bobby Valentine, Mike Hargrove, Buddy Bell, Jim Leyland, Don Baylor and more.

    See omnystudio.com/listener for privacy information.

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    48 mins
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