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 -------- Like this video? Subscribe: null Get unlimited access to Bloomberg.com for $1.99/month for the first 3 months: https://www.bloomberg.com/subscriptions?in_source=YoutubeOriginals Bloomberg Originals offers bold takes for curious minds on today’s biggest topics. Hosted by experts covering stories you haven’t seen and viewpoints you haven’t heard, you’ll discover cinematic, data-led shows that investigate the intersection of business and culture. Exploring every angle of climate change, technology, finance, sports and beyond, Bloomberg Originals is business as you’ve never seen it. Subscribe for business news, but not as you've known it: exclusive interviews, fascinating profiles, data-driven analysis, and the latest in tech innovation from around the world. Visit our partner channel Bloomberg Quicktake for global news and insight in an instant.