Sean ‘Diddy’ Combs’s Empire: Winnowed, but Still Weighty

In arguing to keep Sean Combs in jail until his trial on federal racketeering and sex trafficking charges, prosecutors have portrayed him as a lavishly wealthy, well-connected music mogul who would be well positioned to flee. In court papers, prosecutors cited media reporting that estimated his wealth at close to a billion dollars.

But as Mr. Combs’s reputation has unraveled amid a wave of high-profile lawsuits and criminal charges, so has his business portfolio. Once a major brand ambassador and chairman of a media platform, he has been forced to withdraw from those roles. In June, several months before Mr. Combs was indicted, Forbes estimated his net worth at $400 million, down from $740 million in 2019.

Mr. Combs’s fortune has been at the forefront of his public persona since the 1990s, when the success of his hip-hop and R&B label, Bad Boy Entertainment, meant he was known as much for his high-flying, champagne-popping lifestyle as the music he produced.

One year ago, Mr. Combs, who is known as Diddy, was at the helm of an ever-growing portfolio: He was a record label founder, a liquor promoter, a cable TV and digital media chairman, a philanthropist and a fashion executive with a label called Sean John.

Mr. Combs has gained prominence as a record label executive, a liquor promoter and the founder of a cable TV and digital media platform.Credit…From left: Theo Wargo/WireImage, via Getty Images; Stan Honda/Agence France-Presse — Getty Images; Dimitrios Kambouris/Getty Images for Revolt TV

“He was a larger-than-life marketer,” said Dessie Brown Jr., an entertainment consultant who long viewed Mr. Combs as a model for building a career. “He always talked about being like a ringleader in a circus.”

The circus tents began to fold though, one by one, during a cascade of sex abuse lawsuits that began in November. Mr. Combs, who has denied sexually abusing anyone, agreed to end his lucrative partnership with the liquor giant Diageo amid a legal dispute, and he sold his stake in Revolt, the media company he founded. The value of his music catalog — including stakes in hit songs like “I’ll Be Missing You” and “It’s All About the Benjamins” — has been threatened by his reputational decline.

Representatives for Mr. Combs declined to comment on his finances.

Lawyers for Mr. Combs, who has pleaded not guilty to racketeering conspiracy and sex trafficking charges, are appealing a court’s decision to keep him incarcerated until trial. They assert that their client is far from a flight risk, having voluntarily flown to New York to make himself available for arrest. They have called the onslaught of civil suits — which now number more than 20 — an attempt to extract financial settlements from a wealthy public figure.

Celebrity net worths are the subject of constant speculation, but it can be difficult to estimate a person’s total assets with certainty from afar, especially for someone like Mr. Combs, whose portfolio is largely private and evolving in the shadow of his legal troubles.

“It’s like trying to catch a falling knife,” said Zack O’Malley Greenburg, a journalist and former Forbes editor, who studied Mr. Combs’s finances in 2022.

“I firmly believe that he was at one point a billionaire,” Mr. Greenburg said. “I firmly believe that he is not now.”

A $200 Million Nest Egg

Much of Mr. Combs’s wealth has stemmed from his work with Diageo, which started more than 15 years ago when he began promoting its vodka brand Ciroc. He and Diageo purchased DeLeón in a joint venture deal about a decade ago, and Mr. Combs leveraged his celebrity to promote the tequila brand on social media, in interviews and as a prop in music videos.

A Diageo executive wrote in a court filing last year that the company had paid him nearly a billion dollars during their relationship.

But conflict spilled into public view in 2023, when Mr. Combs’s liquor company sued Diageo, accusing it of typecasting Ciroc and DeLeón as “Black brands” that should be targeted only to “urban” customers. Diageo denied the allegations of racism and accused Mr. Combs of mismanagement.

Their legal battle was still roiling when the singer Cassie filed a bombshell lawsuit accusing Mr. Combs — her former boyfriend and the head of the record label she had been signed to — of sexually and physically abusing her for years. Mr. Combs quickly settled with Cassie, whose full name is Casandra Ventura, but more lawsuits followed.

Part of Mr. Combs’s dispute with the liquor company was over whether he should be allowed to continue to represent DeLeón. After the wave of lawsuits began, Diageo’s lawyers argued that it was “impossible” for Mr. Combs to “continue to be the ‘face’ of anything.”

By January, Mr. Combs and Diageo had resolved their disputes, the lawsuits were dismissed and Mr. Combs sold his half of DeLeón. A public report for investors revealed that the sale was worth about $200 million.

A Catalog Under Threat

The origins of Mr. Combs’s fortune are in his rise as a 20-something music producer whose work helped turn hip-hop into a global pop movement. He started as an unpaid intern, doing legwork for the Uptown Records founder Andre Harrell, before ascending to an executive role by the early ’90s.

With a battle of egos playing out at the record label, Mr. Harrell fired Mr. Combs in 1993, allowing Mr. Combs to take an Uptown talent — the Notorious B.I.G. — to his own company, Bad Boy, which signed a distribution deal with Arista, the major label then run by Clive Davis.

“I fired him and basically made him rich,” Mr. Harrell said in Mr. Combs’s self-produced documentary about Bad Boy’s history.

For years, Bad Boy was a home for some of the hottest artists in hip-hop, including Mase, Craig Mack, Black Rob, Faith Evans and Mr. Combs’s own musical debut as Puff Daddy. After its cultural peak, the label continued to develop talent and record stars — Machine Gun Kelly, Janelle Monáe and French Montana were all at one point signees — but over the years, it went from being an active label with a storied recording studio to a legacy brand whose value lay in its back catalog.

The company eventually moved from the Manhattan office that once served as its headquarters. The building was demolished this year to make room for a high-rise hotel.

Tony Drootin, the former manager of Bad Boy’s Midtown Manhattan recording studio, known as Daddy’s House, said a turning point in the culture of the label came in 2014, when Mr. Combs decided to close the studio. At the time, streaming was upending the music industry, Mr. Drootin said, and real estate prices were skyrocketing.

“It just didn’t make sense monetarily because he could do a lot of what he needed to do in his living room with a computer and a microphone,” Mr. Drootin said.

Despite Mr. Combs’s long history with chart-topping hits, his music catalog now appears to generate only modest earnings, in part because he no longer controls the rights to his most popular albums. Billboard, the music industry trade publication, recently estimated that Mr. Combs currently makes about $1.25 million a year from his recordings and music publishing rights.

If he ever wanted to sell that catalog, its value would likely be depressed by the negative publicity around his legal woes, according to four professionals who are in the business of buying and valuing music catalogs.

Merck Mercuriadis, who founded the music investment company Hipgnosis, likened Mr. Combs’s catalog to that of R. Kelly, which has had steady streaming numbers but not found any buyers.

“No one will ever buy these catalogs,” Mr. Mercuriadis said. “There is no one that is going to risk institutional investment on a catalog that has this kind of noise around it.”

The Fall of Combs Global

By early 2023, Mr. Combs’s business interests were all rebranded under a new name: Combs Global, which came with a vision to build the “largest portfolio of leading Black-owned brands in the world.”

But compared to the bustling days at the Bad Boy offices in Manhattan, the day-to-day work at Combs Global was relatively decentralized.

Most employees worked remotely, and when executives would gather for in-person meetings, they would often take place on the island in Miami Beach where Mr. Combs lived, said a former Combs Global executive who left amid the lawsuits against the mogul.

The company became the umbrella for brands like Love Records, an R&B label that briefly had a deal with Motown for Mr. Combs’s 2023 comeback album — ultimately it came out independently, without Motown’s involvement — and Sean John, the clothing company that Mr. Combs bought back for $7.6 million after its majority owner went bankrupt. The line is now largely unavailable for sale.

Combs Global also oversaw his charitable and more mission-driven work, including his online marketplace for Black businesses and a partnership with a New York charter school network that he helped expand.

“Yes, I’m blessed to be a billionaire,” he said last year in an interview at Invest Fest, an annual event dedicated to Black financial empowerment, “but at the same time, if my people aren’t doing good then I can’t be settled.”

After the first several sexual abuse lawsuits were filed, there was an exodus at his company as many employees — including high-ranking executives — decided they did not want to be associated with his brand anymore. There were also waves of layoffs as Mr. Combs’s business interests slumped.

Mr. Combs settled Ms. Ventura’s lawsuit for what his lawyers have described as an “eight-figure settlement.” But in the wake of a mounting pile of lawsuits, Mr. Combs’s portfolio of brands and causes fell apart piece by piece.

He sold his stake in Revolt, the media company he founded more than a decade ago, for an undisclosed sum. The charter school network ended its partnership with him. His online marketplace, Empower Global, is now defunct.

No More Lavish Lifestyle

As he awaits trial in a special housing unit at the Metropolitan Detention Center in Brooklyn, Mr. Combs endures a lifestyle far removed from his private plane and lavish homes, cars and artworks. His sprawling 10-bedroom mansion in the Holmby Hills neighborhood of Los Angeles, which was raided as part of the criminal investigation, is on the market for $61.5 million.

His home in Miami Beach, Fla., was appraised at $48.5 million. Mr. Combs’s lawyers hoped to use it as collateral for a $50 million bond proposal, but the court rejected that bid last month. (Mr. Combs paid $18 million in mortgage debt to ensure the home could be used as part of the potential bail package.)

Even as Mr. Combs’s financial position appears to be in decline, the government has repeatedly noted that he remains a very rich man, someone whose wealth, investigators contend, increases the potential risk that he will flee if released on bail. As of late last year, the government reported, Mr. Combs had more than $1 million in personal cash “on hand,” as well as dozens of personal and corporate bank accounts containing millions of dollars more and vehicles in multiple locations.

Prosecutors said Mr. Combs’s wealth enabled him to employ a web of associates who helped facilitate sex trafficking and cover up his crimes. Those efforts, according to the government, included attempts to obtain hotel security footage to help hide a brutal assault of Ms. Ventura in 2016.

“The story he built around his wealth now poses a problem for his defense,” said Zakiya Larry, a public relations and crisis communications specialist, “and it has become ammunition for the prosecution.”

But the wealth also supports the large defense team of lawyers led by Marc Agnifilo, who has represented high-profile defendants such as Keith Raniere and Martin Shkreli.

Those lawyers are trying to arrange his release by promising to install a large, and expensive, team of private security staffers to monitor him at all hours while he stays at his home in Miami Beach. The team, which they propose would be led by a former police detective who once worked on security details for President George W. Bush and Vice President Al Gore, is designed to rebut the government’s contention that, beyond fleeing, Mr. Combs would use his freedom to intimidate potential witnesses.

“Even if the court doesn’t fully trust him, trust the package as a whole,” Mr. Agnifilo said in court last month.

Prosecutors have been resisting the defense’s proposal. In arguing against it in a recent filing, the government once again took aim at Mr. Combs’s unusual wealth, saying that he should not be able to “pay his way out of detention.”

Kirsten Noyes contributed research.

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