The Life of the Party

Your FAVORITE RAPPER'S FAVORITE BILLIONAIRE loves nothing more than to have a few hundred of his famous friends over to his Hamptons estate. How did a sports-licensing CEO from Lafayette Hill, Pennsylvania, become this generation's Gatsby?

- DAN ADLER

MICHAEL RUBIN AND Lil Baby first met in the Bahamas. The CEO and the rapper found themselves, in January 2021, sitting around the same baccarat table with their mutual friends Drake and Meek Mill. Baby had begun making music a few years earlier after serving two years related to drug and weapon charges in Atlanta. Now, like the two other rappers placing their bets, he was beginning to mix with billionaire businessmen.

"We ain't win," Baby recently recalled. "We had a great night, though."

As with Drake and Meek, Rubin, 51, struck up a friendship with the 28-year-old rapper. Each of the three has recorded lyrics about him, but Baby put it the most bluntly on a 2022 song: "I get my advice from Mike Rubin." "He's got the best story ever," Rubin said, sitting nearby. "Because this guy didn't even rap until he got out of prison, and it shows you, you can do anything at any time in your life." They were in a Sprinter van on a Tuesday morning in June, heading from a Harlem school to get to Rubin's company jet at LaGuardia. Fanatics, the sports merchandise business (jerseys, cards, more) that Rubin has run since 2011, was holding its inaugural Merch Madness event. In cities including Los Angeles, Miami, and Dallas, a wealth of athletes and musicians including Donovan Mitchell, DJ Khaled, Quavo, and Chris Paul-most of them personal friends of Rubin's-gave out licensed apparel to local kids and families in need. It was an instance of the philanthropic bent Rubin has demonstrated in recent years as well as of the eye-popping and mildly befuddling constellation of personalities he has assembled around himself over the same period.

Rubin and Baby boarded the plane.