Billionaire Boys Club: A Look Inside Rapper Sean Combs Sexual World Finds Eerie Similarities To Jeffrey Epstein, Including Wall Street Ties

New York Post

(New York Post) Sean “Diddy” Combs aggressively marketed himself to the ultra-rich as he turned his edgy rap glamor into a billion-dollar fortune.

Billionaires told The Post he would cold email with business proposals, while other Wall Streeters acclaimed him as a “genius” and one CEO of the New York Stock Exchange called him an “inspiration” on a par with the Founding Fathers

Sean 'Diddy' Combs giving an interview at the opening bell of the New York Stock Exchange on April 3, 2006
Diddy’s status as a Wall Street tycoon in his own right was on show in 2006 when he rang the New York Stock Exchange opening bell. Getty Images

But after federal investigators raided his Los Angeles and Miami homes as part of what law enforcement sources have told The Post is a sex-trafficking investigation led by the Southern District of New York, his career as an entrepreneur and investor is in jeopardy. Diddy has denied wrongdoing and called the probe “a witch hunt.”

Diddy was first declared a billionaire by hip-hop wealth expert Zack O’Malley Greenburg in 2022, but had coveted the status for years, telling Forbes in 1999, “I wanted to be very, very rich.”

Ronald Burkle and Sean 'Diddy' Combs posing for a picture at the Sean John Underwear launch party at Light in Las Vegas, Nevada on August 27, 2007
Diddy’s relationship with billionaire Ron Burkle appears to be his longest business relationship. In 2015, Diddy again teamed up with Burkle and Mark Wahlberg to buy now water company AquaHydrate. Johnny Nunez/

Along the way he acquired a Rolodex littered with bold-faced names: he partnered with billionaire investor Ron Burkle; was “mentored” by hedge fund guru Ray Dalio; had his fashion line sold in Macy’s and Dillards; went into business with alcohol giant Diageo; opened the New York Stock Exchange with Estée Lauder heir William Lauder; struck deals with Zac Posen and Liz Claiborne; 50% owned his own TV channel Revolt; launched a water range with Mark Wahlberg; and teamed up with Salesforce’s Marc Benioff to launch a black business marketplace.

In 2003, he sent the then owner of the Dallas Maverick Mark Cuban an email asking to design the uniforms for the NBA team, Cuban told The Post. They had never met so the cold email was a bold move.

For Diddy, it was a slam dunk to associate his new clothing brand, Sean John, with a pro sports team.

While Diddy took credit for the design, it was actually Diddy’s top designer who created it and Diddy signed off, Cuban said.

Dallas Mavericks center Erick Dampier taking a shot over Atlanta Hawks guard Royal Ivey during a basketball game at Philips Arena in Atlanta, 2004
Diddy asked to design the Dallas Mavericks’ uniforms in 2003, securing his Sean John clothing logo a place on an NBA team, and with it both respectability and TV exposure. AP

“We were an up and coming team at a time when pro sports teams didn’t do anything with entertainment industry people,” Cuban said.

“We never even met… we never did any follow up or anything beyond that,” Cuban said.

For Diddy — who had gone to Howard University to study business — a single deal with an NBA team gave him credibility that he leveraged for even more dealmaking.

But it was a two-way street: Diddy also used his own cache — the promise of entry into a world of celebrity — to attract investment for his projects.

The same year as his Mavericks deal, Diddy got Burkle, a serial investor worth an estimated $2.9 billion according to Forbes, to inject $100 million into his fashion range Sean John.

Michael Jackson, Sean P. Diddy Combs, and Ron Burkle posing for a photo at The Return of Gatsby 2003 MTV Movie Awards Post Party"
Michael Jackson (left), Diddy (center) and Burkle (right) attended an MTV party together in 2003. Burkle purchased Jackson’s ranch Neverland for $22 million in 2020.

It was to become Diddy’s longest-standing Wall Street relationship. After it was done, they partied with Michael Jackson — while Sean John became a fixture in Macy’s and Dillards stores.

The next year the rapper teamed up with Estée Lauder to create multiple fragrances, including one that was named “Unforgivable.”

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