Diddy And Gatsby

As investigations swirl, it's worth exploring how Diddy built his empire with the help of Gatsby-esque revelry—and pulled figures from Jay-Z to Donald Trump into his orbit.

Unless you spent the past week hiding under a bottle of Ciroc, you’ve seen the news unfolding around Sean “Diddy” Combs. Federal investigators raided the mogul’s homes in Los Angeles and Miami; it’s not clear what they found, or what the consequences might be. Diddy has been trailed by the specter of violence for decades, and though he maintains his innocence amid the current investigation, it seems he’s reached the end of his Teflon status. At the very least, it would appear his days as a billionaire are over, given how closely the business interests that comprise his wealth are tied to his reputation.

As we wait for answers from the authorities, I’d like to offer some context as a longtime observer of wealth in America, particularly in the hip-hop realm. Watching the walls apparently closing in on Diddy, I can’t help but think of another controversial American celebrity: Jay Gatsby. To be clear, I’m not insinuating Diddy will meet the same fate as F. Scott Fitzgerald’s character, nor am I suggesting Gatsby’s misdeeds match those attributed to the embattled impresario. But it’s an interesting—and possibly instructive—comparison.

Perhaps most intriguing is how Gatsby and Diddy both accumulated money, power, and respect by throwing elaborate parties on Long Island and upending existing social hierarchies, albeit with different goals. Whereas Gatsby seemed primarily focused on romance, Diddy wanted power. And his annual “White Party” in the Hamptons lured some of the biggest—and most polarizing—names on the planet, from Russell Simmons to Donald Trump. The following excerpt is adapted from my 2018 book, 3 Kings: Diddy, Dr. Dre, Jay-Z, and Hip-Hop’s Multibillion-Dollar Rise.

Diddy knew that hip-hop was an aspirational genre; he simply took the aspirations higher, and found a huge market for his message. A series of songs that he rapped on, produced, and/or released through his Bad Boy label held the top spot on the charts for forty-two weeks of 1997. His Puff Daddy and the Family tour grossed $15 million that year, the most in rap history to that point.

Diddy personally pocketed $53.5 million in 1998, thanks mostly to an outsized album advance from Arista. He plowed a chunk of his gains—about $2.5 million, according to reports—into a modernist East Hampton mansion designed by Charles Gwathmey. The brightly painted house stood on an isolated plot overlooking Gardiner’s Bay, seven miles from the more desirable (and pricier) real estate on the Atlantic coast closer to town.

Diddy had taken his Harlem swagger and Timberland boots to suburban America; now he was going to put the violence of the mid-1990s coastal conflict behind him by exerting his cultural clout on one of the country’s wealthiest enclaves. He had his new home slathered in white paint and appointed its interior with fine Italian furniture. It would serve as the backdrop for an annual bash with a dress code more rigid than that of the snootiest country club. He called it the White Party.