George Steinbrenner’s decision back in 2004 to pair Derek Jeter and Alex Rodriguez—two generationally talented baseball players—turned out to be one of the biggest and arguably most successful deals in New York Yankees history. Or all of sports history for that matter.
The results that sprang from the Boss’s machinations became clear: a perennially contending team, a 2009 World Series championship and yes—a lot of headlines. For Jeter, all of that on-field success—and his ability to manage it so gracefully—made him one of the most sought-after athletes both during and after his baseball career. On the latest episode of The Deal with Alex Rodriguez and Jason Kelly, he tells the backstory of how Michael Jordan made him the first baseball player to be endorsed by a then-nascent Jordan Brand, and reveals some never-before-heard details of his tumultuous, three decade-long relationship with A-Rod.
Jeter distinguished himself during a 20-year career played entirely for the Yankees, winning five World Series rings during that time. The last of the titles (and the last time the Yankees won it all) was accomplished with Rodriguez just a few feet away at third base. The pair had known each other since they were teenagers and even shared a 1997 cover of Sports Illustrated.
Jeter was a first-ballot Hall of Famer, inducted into Cooperstown in 2020 with 99.7 percent of the vote. Shortly after retiring, he joined the ownership group of the Miami Marlins and served as the team’s chief executive (the first Black man to hold such a position in Major League Baseball), overseeing both the business and operations of the club. He resigned in 2022, citing strategic differences with his fellow Marlins owners.
Of late, Jeter has been splitting his time between his young family, investing, endorsements and broadcasting—reuniting with Rodriguez to provide on-air baseball commentary.
Listen to The Deal on Apple Podcasts, Spotify, iHeart, Bloomberg Carplay, or wherever you get your podcasts. You can also watch The Deal on Bloomberg Originals and Bloomberg TV.
00:00 - 01:00 Intro
01:00 - 03:16 - How Derek and Alex met
03:16 - 07:45 - Derek's Early Days with the Yankees
07:45 - 12:15 - Playing in New York & Arbitration
12:15 - 17:18 - George Steinbrenner
17:18 - 19:41 - Alex Comes to New York to Play Third Base
19:41 - 23:00 - 2009 World Series Championship
23:00 - 25:31 - Derek's thoughts on media
25:31 - 28:55 - Derek joins Jordan Brand
28:55 - 30:35 - Derek's decision to retire
30:35 - 32:00 - Business after baseball
32:00 - 36:25 - Derek's reflection on the Miami Marlins
35:25 - 37:36 - Investment philosophy
37:36 - 44:07 - Alex and Derek on working together at Fox
44:07 - 48:00 - Derek's future & legacy
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