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

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 opened up more opportunity for Cardinale to be an investor. He teamed with Dwayne “The Rock” Johnson and Dany Garcia to restart the XFL, and the trio subsequently engineered its merger with the USFL, the other big springtime pro -football league, to create the UFL. The new-look league played its first game earlier this week.

In 2021, Cardinale’s ambitions in team ownership led RedBird to buy a piece of Fenway Sports Group, the Boston-based company that owns the storied Red Sox baseball team, the Pittsburgh Penguins in hockey and Liverpool FC in English football. Cardinale then went a step further in soccer, buying AC Milan, one of the best-known clubs in the world.

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00:00 - 01:05 Introduction
01:05 - 05:21 The YES Network deal
05:21 - 07:36 Goldman Sachs in the nineties
07:36 - 12:01 Legends Hospitality & Jerry Jones
12:01 - 16:24 The uncertainty of the YES deal
16:24 - 21:31 Gerry & Alex on rebuilding the Yankees in 2008
21:31 - 23:28 Gerry’s relationship with George Steinbrenner
23:38 - 26:25 George Steinbrenner’s letter to Alex
26:25 - 36:49 Buying AC Milan
36:49 - 40:11 What Gerry learned about ownership from George Steinbrenner
40:11 - 42:01 Why invest in Italian football?
42:01 - 45:18 Inside the XFL
45:18 - Gerry’s advice for young people

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