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.

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.

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. Cardinale then went a step further in soccer, buying AC Milan, one of the best-known clubs in the world.

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