“This is the police! We have a warrant! Come out with your hands up!”
Last March, a caravan of law enforcement cars and trucks announced their arrival via loudspeaker before busting through the main gate of 2 Star Island Drive—the luxurious oceanfront residence that Sean “Diddy” Combs purchased from music executive Tommy Mottola back in 2003 for $14.5 million.
Accessible only by water or a single narrow bridge, this manicured man-made island in the middle of Biscayne Bay is usually off limits to outsiders. But on the afternoon of March 25, 2024, the Feds were everywhere. A helicopter hovered overhead and a police boat pulled up to the marina behind the opulent home where Diddy had entertained A-list celebrities and industry power brokers for decades. Now the place was overrun by a joint task force of officers from the Miami Police Department, FBI, and Homeland Security Investigations, who spent hours carrying out cardboard boxes of evidence and plastic bags of laptop computers and cellphones.
Meanwhile a similar scene played out 3,000 miles to the west as Diddy’s 10-bedroom 13-bath Los Angeles mansion on “Billionaire’s Row” in Holmby Hills—not far from Hugh Hefner’s Playboy Mansion—was simultaneously raided by heavily armed federal agents accompanied by camera crews who beamed the spectacle around the world live.
Sitting in my New York City apartment, watching red-and-blue lights flashing on my iPhone, I was reminded of my own experience at Star Island ten years earlier, and everything I saw at that “grown-and-sexy” Diddy after-party. My thoughts turned to Sean Combs’s remarkable rise through the entertainment industry, and how the self-proclaimed “Bad Boy for life”—a figure who once topped the pop charts with a song proclaiming “Can’t nobody hold me down”—was now facing the fight of his life. Looking back on that moment, just days before United States v. Diddykicks off with juror selection on May 5, it’s clear that even if Sean Combs, who has denied all charges, has hosted his final “freak off,” the shadow of the Puffy party era still lingers.
The rise of Diddy
The raid came just four months after Diddy settled a lawsuit filed by his ex-girlfriend and former Bad Boy artist Cassandra Ventura, which detailed years of “savage” sexual, physical, and emotional abuse. Federal agents confiscated drugs and firearms, not to mention Diddy’s so-called “freak-off supplies.” Who can forget the memes about those 1,000 bottles of baby oil? The media feeding frenzy conjured sordid fantasies of marathon sex parties and fueled rampant speculation about which celebrities had been captured on the supposed stash of surveillance videos.
Parties have always been central to the Sean Combs phenomenon. Back when folks called him Puff Daddy, Combs made his name hosting jams at Howard University in the late 1980s before moving to New York, where he helped to make Mecca, a Sunday night party at The Tunnel, the center of the hip-hop universe. There’s no denying that Puffy’s parties changed the game, playing a crucial role in hip-hop’s transition into the hottest force in mainstream pop culture. Diddy’s taste in music, dance, and fashion made his seductively shiny brand of rap music the soundtrack for a generation of “ballers, shot-callers” who created a booming new economy around Black culture, earning Combs, his affiliates, and his imitators billions of dollars in the process.
For better or for worse, lavish parties defined Diddy’s transcendent trajectory, from the tragically overpacked 1991 charity basketball game at City College New York that ended with nine people crushed to death to the 12,000-square-foot Hamptons estate he rented for Biggie’s “Juicy” video shoot—“celebratin’ every day, no more public housing”—to the fateful party he and Biggie attended at the Petersen Automotive Museum in Los Angeles on the evening of March 9, 1997, to his over-the-top 29th birthday bash at Cipriani on Wall Street the following year, whose star-studded VHS invitation featured shout-outs from the likes of Oprah Winfrey, Tommy Hilfiger, Mariah Carey, and Donald Trump. Puffy, Diddy, Love—the nickname changes reflected an incessant process of reinvention. The son of a Harlem hustler whose story had no happy ending, Sean Combs came into the game as a young Black man from money-earnin’ Mount Vernon who saw himself as one of those larger-than-life names. He sometimes referred to himself as “the Black Sinatra,” and by the time he copped a mansion in the Hamptons, the legendary “white parties” he hosted there looked like something straight out of an F. Scott Fitzgerald novel. “Have I read The Great Gatsby?” he replied to a reporter in 2001. “I am the Great Gatsby!” But of course Gatsby—published 100 years ago—was an American tragedy.
The man who spent half a million dollars on his 1998 birthday party celebrated his 55th trip around the sun last November at Brooklyn’s infamous Metropolitan Detention Center, where he now awaits trial on charges of racketeering, conspiracy, and sex trafficking.
“I watched grown men damn near cry to get into a Puffy party”
I first heard of Puffy in 1993 during an editorial meeting to plan the first issue of VIBE magazine. Scott Poulson-Bryant, our senior staff writer who came up with the magazine’s name, pitched a story about a young party promoter, stylist, video director, producer, and A&R man at Uptown Records who was responsible for the success of Jodeci and Mary J. Blige. Scott spent weeks reporting the first in-depth profile of Sean Combs, which I had the pleasure of editing. Just as our story went to press Puffy’s mentor Andre Harrell fired him. He would soon link with Arista Records founder Clive Davis, who cut him a massive check and the Bad Boy era was born. Puffy wasted no time signing MCs Craig Mack and Biggie Smalls, and R&B chanteuse Faith Evans to build out his starting lineup—but the real star of Bad Boy was always Sean himself. Although Death Row CEO Suge Knight was often cast as the bad guy in their rivalry, Suge’s speech at the 1995 Source Awards about Puffy being “all in the videos” was pretty much on point.
As the Bad Boy empire grew, so did VIBE. Some consider the opening party for the 1995 VIBE Music Seminar at the Tavern on the Green to be the precursor for Puffy’s all white parties in the Hamptons. “I remember when that shit was the hottest ticket in the world,” says OG hip-hop journalist Michael Gonzales. “ I just wanted to be as far away from it as possible. First of all, I ain’t a n*gga that’s gonna be wearing all white unless I’m on a safari somewhere. Plus I heard people would wake up in the guest bedroom with their pants off.”
Because there is “no upside” to speaking about Puffy, one Black entertainment executive I interviewed requested anonymity. “Now the whole world is piling on,” he says, “and nobody wants to talk about the fortunes that were made, entire industries that did not exist. There were obviously bad things he was involved in. There were also important things that he was involved in.” This particular exec, who still refers to Diddy as “Sean,” and knew him well and did much business with him over a 30-year period, swears that he never heard of a “freak off” until it was all over TMZ. “But I will tell you the truth,” he says in a quiet voice, “flossing while Black is a very dangerous game. This was the first time in history that the business person was the artist as well…Those parties changed everything. I watched grown men damn near cry to get into a Puffy party. There was no higher honor than to be in one of his events.”
The birth of the “All-White Party”
Puffy’s White Parties officially started in 1998, a time when Combs was trying to put the tragic murders of Tupac Shakur and Christopher Wallace behind him and embrace his own stardom. After spending $2.45 million for a 4,500-square-foot waterfront mansion on Hedges Bank Drive in East Hampton, he decided to throw a housewarming party. “So I moved into this new neighborhood,” Combs recalled during an interview in 2009. “They were like, ‘What’s this hip hop guy movin’ in?’”
“Everybody come on over,” Puffy told his neighbors. “Let me invite some of my friends from Harlem from 145th Street. Let me mix you all together and see you ain’t got nothin’ to be afraid of. You ain’t gotta hold your pocketbooks tight or nothin’ when I’m joggin’ in the neighborhood.”
“I remember the first party he threw in the Hamptons,” Paris Hilton recalled to The Hollywood Reporter 20 years later. “It was iconic and everyone was there.” Leonardo DiCaprio was in the house, fresh off the release of Titanic. “Having an entire party all dressed in white was a stunning sight,” Martha Stewart said. Guests were turned away at the door for wearing beige or black shoes. “‘I wanted to strip away everyone’s image and put us all in the same color, and on the same level,” Puffy would explain to Oprah. Years later he was quoted as saying “I feel safe in white because deep down inside, I’m an angel.”
That was the same year VIBE put Puffy on a split cover—one styled as an angel and one as a devil. Last summer my colleague Danyel Smith wrote about her ordeal as the magazine’s editor-in-chief during that time. I was aware that Puffy wanted to get a look at the cover ahead of time, and that Danyel was standing on business. I didn’t know that he told her he’d see her “dead in the trunk of a car” if she refused. Puffy likes to remind people that he’s from Harlem, but Danyel is from Oakland and she did not back down. Not long after that, the servers that contained the digital files of our magazine pages disappeared mysteriously from the office. Nevertheless the magazine came out without delay, and without any apology. Sacha Jenkins’s cover story is a prime example of hip-hop journalism at its finest. In it, he confronts Puffy about calling a young female editor at VIBE, irate about a photo caption in an earlier issue of the magazine. “I’m gonna hunt that bitch down,” he threatened.
“I was an irate parent calling the school,” Puffy said of the outburst. “There was a picture of me and my son [on the “I’ll be Missing You” video set], and he was holding a pink water gun. And it said, ‘Didn’t Puffy learn yet?’ But everybody’s children play with water guns!”
Bönz Malone, the storied hip hop ambassador, A&R, actor, graf writer, and essayist, is a man of many talents. In addition to writing his monthly column “Tuph Street,” and the occasional feature or cover story, he was listed on VIBE’s masthead as our consigliere, a term familiar to fans of The Godfather trilogy. Bönz is a man of respect whose relationships from the streets to the suites helped the VIBE editorial team navigate sticky situations such as this one. He took it upon himself to address the matter in his own way.
The Monday after Puffy’s threatening phone call, Bönz put on a crisp tailored suit and paid a visit to the Bad Boy offices with a Bible in his hand. “They were like, ‘Ah, don’t let him in! Don’t let him in!,’” Bönz recalls. “I’m dressed like one of Jehovah’s Witnesses. I can hear him yellin’ in the background, “Nah, don’t let him in!”
The next day Bönz reached out to Puff’s then-manager, Benny Medina. “It was the first time I ever spoke with him,” VIBE’s consigliere recalls. “I called him up. I said, ‘Yo, I gotta see you, man.’”
“Come to my hotel,” Medina told him.
“I said, ‘Yeah, OK. You better have clothes on! Cause if you come to the door naked I’m gonna bust your ass, period. I’m not havin’ none of that shit.’ He could hear in my voice that it was something serious. He was stayin’ at the Sheraton… I got up there and he opens the door. I see he’s got his clothes on. ‘Alright, that’s cool. Now we could go forward,’ I said. ‘Tell your man to stop gettin’ high. Because he’s gettin’ sloppy. And if he goes over the line again that’s it. There’s gonna be no conversation whatsoever.’”
(Complex reached out to Medina via email for comment. As of publication we’ve received no response.)
Some time later, Puffy was invited to take part in the so-called Big Willie Panel at an industry event called the VIBE Music Seminar. That “Big Willie” was popular hip-hop slang at the time did nothing to make the panel any less tasteless. As Danyel wrote in the Times, the term was not just a word to describe a big boss, but “a euphemism for a large penis.” Adding insult to injury, “VIBE honchos organized ‘Big Willie’ panel discussions,” the former editor-in-chief wrote, “when female artists and executives were working twice as hard for less money and only whispered credit.”
Bönz stepped to a microphone during the audience Q&A and asked Diddy whether Bad Boy Entertainment’s plans for the future included threatening female journalists. “It’s not about no violence,” Combs replied as Bönz walked away.
The Diddy party spinoffs
In the years that followed, Puffy’s white parties became an institution, taking place at his East Hampton waterfront home over the Labor Day Weekend. In 2004, he and his entourage arrived on twin helicopters—one red white and blue and the other military camo—and he walked around the party showing off a rare copy of the Declaration of Independence to promote his “Vote or Die” campaign. The summer soirees, sometimes lasting multiple days, would later branch out to St.-Tropez and Beverly Hills, California, when Combs moved to the West Coast. There were Fourth of July spin-offs too—and eventually there were imitators.
In the summer of 2021, Michael Rubin, the CEO of the sports merchandise company Fanatics, and co-founder—with Jay-Z and Meek Mill—of the Reform Alliance, began throwing his own “white parties” at his $50 million Bridgehampton home. Guests included Jay and Beyoncé, Megan Thee Stallion, and MLB commissioner Rob Manfred. The guest list grew ever flossier in years to come.
Fourth of July 2023 marked a bittersweet milestone for Combs. Although it was the 25th anniversary of his first White Party, Rubin’s party had officially upstaged the original. Much to Combs’ consternation, the biggest stars—your Leo DiCaprios, your Tom Bradys, your Drakes, your Kardashians—were dressing up in white and flocking to Rubin’s mansion to pop bottles and smile for the flashing cameras. Leave it to my old friend Elliott Wilson to stoke the controversy. “Can’t believe Puff let a white brother take July 4 Hamptons white away from him,” Wilson posted on X. “Take that! Ha.”
“I’ve never been to a Diddy party,” Rubin said during a Breakfast Club interview last year. “And he’s never been to one of my parties in my life.” Even before the raids on Diddy’s home the whole idea of a white party in the Hamptons seemed to be losing its allure. Kai Cenat turned down an invitation to Rubin’s 2024 party, and some even speculated that Kendrick Lamar released his “Not Like Us” video on July 4 to contrast with Drake’s expected attendance at the lavish event. Rubin considerately banned the song from being played out of respect for his Canadian guest. This year Rubin has quietly canceled plans for any future white parties. “With all the Diddy controversy it’s just not a good look,” said one staffer at the Reform Alliance, who spoke on condition of anonymity. Another anonymous source said Rubin’s white parties were “canceled forever,” blaming Diddy’s legal troubles for giving the theme “such a bad stigma after everything that came out this past year.”
Inside Diddy’s White Party
As I stared at my phone, watching law enforcement officers breaking down the ornately carved wooden gate at 2 Star Island Drive, I remembered standing outside that gate whispering the secret password to gain entry to a party inside.
Ultra Weekend 2014 had Miami Beach fully turnt as models in swimsuits rode up and down Collins Ave in Lamborghinis. On the last day, Diddy popped up at Red Bull Guest House for an impromptu late-night preview of 11 11, his collaborative album with Israeli DJ Guy Gerber which marked the hip-hop mogul’s first foray into the surging, and largely Caucasian EDM market. All weekend long, superstar DJs like Skrillex, Diplo, Steve Aoki had been throwing down at rooftop pool parties filled with A-list guests. But Sean Combs brought a different kind of energy. Dressed in black from his leather bucket to his kicks, offset by a gold chain and Jesus piece, he grabbed the mic to introduce his new project for the invitation-only crowd. “I personally wanted to call it Ketamine,” he said of the album. “It ain’t for everybody…it’s for demented, after-hours minds.”
After pressing play Diddy hung out for a bit to soak up the afterglow. Reshma B, a fellow music journalist, snapped a quick photo with Diddy while I navigated past his hulking bodyguard to ask the music mogul if he remembered me. “What up, playboy?” he replied as we dapped each other up. We were hardly on a first-name basis, but after 17 years at VIBE I’d met Puff on more than a few occasions. I figured there would be an after-party somewhere and I asked if it would be cool to pull up. Puff gave me the OK and told his bodyguard to tell me the details. “Two Star Island,” the hulk said. “Come after 3 AM and ask for ‘Marcus’ [this was a pseudonym] when you get there.”
Me and Reshma B showed up before dawn and found a dozen or so interlopers milling about on the street outside Diddy’s gate. They didn’t know the password but we did and the gate swung open just enough for us to step through. The guard inside warned us to keep our phones in our pockets or they would be confiscated. Walking down the palm-lined pathway, I thought about the island’s history. This was the same place Diddy invited Chris Brown and Rihanna to reconcile weeks after the violence between them on Grammy night 2009. Pulsating bass-heavy rhythms grew louder with each step until we came upon a long, shallow, rectangular pool. In the water were a half dozen women in skimpy swimsuits dreamily gliding back and forth wearing masquerade masks with devilish horns attached. Unsure what to make of this spectacle, I told myself Miami is a city where scenes from rap videos are always bleeding into ordinary life—cars with spinners, bottles with sparklers, video vixens in the VIP as far as the eye can see. When all of that becomes old hat, what better way to make a splash than some Eyes Wide Shut shit?
All the bars were fully stocked with Ciroc in every flavor as well as bottles
of Diddy’s new premium tequila brand, DeLeon. By early 2014 Diddy was officially ranked hip-hop’s “Cash King,” according to Forbes, whose reporters estimated his earnings over the previous year to be $50 million—a modest sum by today’s standards, but enough to edge out Jay-Z at $43 mill and Dr Dre at $40 mill. Forbes attributed Diddy’s standing to his lucrative Ciroc endorsement deal with the $80 billion international liquor megacorp Diageo. But after 20 years as a CEO, he knew the hardest part of being on top was holding onto your spot.
A few months after the Star Island after-party, Apple would acquire Beats by Dre for $3 billion in cash and stock. Jay-Z and Beyoncé were already certified as the world’s highest earning celebrity couple, and the value of Jay’s ownership stake in Ace of Spades champagne had not even begun to pop. Although Diddy had no equity in Ciroc, he was proud of his DeLeón joint venture. “This is a historic day for Sean Combs as a businessman, and even hip-hop,” he told me in January 2014, two months before the Star Island party. “I’m not starting this from scratch. This is the first company I’ve ever bought. I couldn’t go and buy Ciroc from Diageo, but we are buying this together.”
The DeLeón deal would ultimately prove to be a disappointment. In May 2023, Combs filed suit against Diageo, claiming that the spirits corporation had failed to market DeLeón properly because they “typecast” the tequila as a “Black brand” that could only be sold on the “urban” market. The dispute effectively ended a lucrative working relationship between Combs and Diageo, who reached a settlement in January 2024, a few months after Combs was hit with a series of lawsuits relating to sexual assault charges.
But during that Star Island after-party, the future still looked bright. Diddy’s staff were quietly efficient even in the wee small hours of the morning. I noticed that every server and security guard was a person of color while the more menial jobs—sweeping the patio, collecting empty cups, picking cigarette butts out of the grass—were handled by white folks. Reshma made her way out back to where Diddy kept his Jet Skis and posed for a photo by the water’s edge without getting her phone snatched. The sun was just beginning to rise when Diddy, now dressed in white, appeared on an upper balcony to make an announcement. “OK party people, the real party is about to begin,” he said matter-of-factly. “The rest of y’all can grab whatever bottles you want, but you need to get up outta here.” We made our way back to South Beach, red plastic cups of coconut Ciroc in hand, none the wiser about what “demented after-hours minds” had planned for the after-after party.
The after-after party
“Ain’t no party like a Diddy party,” as LeBron James once observed. Sean Combs may be one of the most prolific hitmakers in music history, one of the most influential shapers of late 20th century popular culture, one of the most successful entrepreneurs in the rap industry—but more than his work on the stage, in the studio, or in the boardroom, Sean Combs legacy has been shaped by his lavish soirees. Those star-studded, over-the-top events have always been the stuff of legend, but now nobody wants to talk about them.
None of celebrities, executives, or public figures who ever attended one of Diddy’s famous functions can go outside without some roving TMZ camera person asking whether they ever took part in a “freak off.” Even Reshma B’s dog Pup Daddy now goes by Pup D. “As soon as the news broke I was getting WhatsApp messages from overseas,” she says. “They were like, ‘Your dog might want to consider a name change.’ It’s just not a good look.”
Transforming rap from an authentic subculture with its own ethics, morals, and codes of conduct into a bankable business that’s still “All About the Benjamins” involved the celebration of excess, decadence—even sexual exploitation. Sean Combs was hardly the first to discover this formula, which is really as American as apple pie. Gordon Gecko’s “greed is good” mantra is alive and well even amidst flagrant deception and corruption in high and low places.
But across the entertainment industry, folks are rethinking the over-the-top bacchanalia that were once the norm in hip-hop circles. The end of Diddy’s reign represents that reckoning. Kendrick Lamar might have put it best when he released his untitled track last September 11, 2024. Maybe it is time to “watch the party die.”
