The Goldman Alum Who Reimagined the Yankees and AC Milan | The Deal

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From George Steinbrenner to Jerry Jones, Gerry Cardinale has done deals with some of the biggest names in sports. These days, the Goldman Sachs alum is making moves under the auspices of RedBird Capital, the firm he created in 2014. His purchase of the AC Milan soccer franchise and the resurrection of American football’s XFL stem from two decades spent at the intersection of sports, finance and media. Back when he was starting out on Wall Street, that nexus was a lot less obvious. “I happened to hit an inflection point in sports that I couldn’t have possibly seen coming,” Cardinale said on the latest episode of The Deal with Alex Rodriguez and Jason Kelly. “We really hit an air pocket where you could really take off. Now the challenge is navigating that, because now everybody’s discovered sports.” At Goldman, Cardinale got a chance to give advice to none other than Steinbrenner, aka “The Boss,” most notably about the 2002 launch of the YES Network. That debut brought its own made-for-TV drama, pitting Steinbrenner against New York Knicks and New York Rangers owner James Dolan (who also controls Madison Square Garden). Cardinale was in the middle of that fight as a key adviser to Steinbrenner—and his work took him deep into the Yankees front office. “That really was sort of the career moment for me,” Cardinale said. “And I haven’t looked back. You really had that partnership with the Yankee organization, the Steinbrenner family—it’s been instrumental in everything I do.” Cardinale and Rodriguez recall a Manhattan dinner they shared with Yankees President Randy Levine where they mapped out the roster that would ultimately deliver the 2009 World Series championship to the Bronx. Around the same time, Cardinale and Goldman teamed up with the Yankees and the Dallas Cowboys to create the hospitality company Legends, born in part out of Cardinale’s desire to link the ambition of Steinbrenner to the only other owner who could match him: Jerry Jones. Leaving the lucrative confines of his Goldman partnership also ope