Rapper unraveled: How Diddy's world fell apart in one year

At the center of it all was Sean "Diddy" Combs in a leather jacket and Cartier sunglasses cutting into a bright red cake featuring artwork from his latest release. It was the mogul's 54th birthday party, as well as a celebration of his "The Love Album." As far as partygoers and paparazzi could tell, he was on top of the world.

Since his rise to fame in the late 1990s as a rapper and producer, Combs had built a business empire and become one of the richest and most well-connected entertainers of all time.

Behind the scenes that November, though, Combs' life was about to start crumbling. Negotiations were failing between Combs and the R&B singer Cassie Ventura, his ex who was on the brink of going public with details of their relationship.

Exactly one week after his star-studded party, the tensions bubbling under the surface boiled over when Ventura sued Combs. The lawsuit alleged a cycle of physical abuse, as well as rape by Combs, who Ventura also said forced her to have sex with sex workers.

Combs' lawyers alleged that her lawyers tried to extort $30 million in exchange for stopping a tell-all book about their 10-year relationship last year.

He eventually apologized to Ventura after CNN released surveillance footage of him physically abusing her at a hotel in 2016. He settled the lawsuit and, at the time, denied any wrongdoing — a stance he has maintained amid a flurry of subsequent allegations — but it marked the beginning of a year that turned his world upside down.

Over the next 12 months, Combs went from being one of the richest music moguls in history, known for his wide network in the entertainment industry and business savvy, to being behind bars, facing a criminal indictment, dozens of civil lawsuits, and an empire in decline.

Combs' freedom, reputation, and finances are all in jeopardy. If he's found guilty of criminal charges, it would mean one of the most celebrated entertainers is also a heinous criminal.

"He looked like he was the king of the world — as flossy as possible, blinged out, with the family, and everything's good," Kenny Hull, a reality show director who worked on the second iteration of "Making the Band," which featured Combs, told Business Insider about the last time he saw Combs, a few years ago at a park in Los Angeles.

"From the top to the absolute bottom," he added. "Canceled and done."

Combs has vehemently and consistently denied all accusations of sexual assault and sex trafficking since Ventura's lawsuit was filed, and each time a new allegation has been made against him.

"Mr. Combs never sexually assaulted or trafficked anyone — man, woman, adult or minor," lawyers for Combs told BI.

A birthday behind bars

Combs celebrated his 55th birthday not at a luxe international club but at the notorious Brooklyn Metropolitan Detention Center, where, a person previously told BI, he was sharing a dormitory with the crypto fraudster Sam Bankman-Fried.

Instead of flowing Champagne or DeLeón, a jailhouse dinner was served on Combs' November birthday, consisting of Salisbury steak or black-eyed peas, mashed potatoes, and green beans. There was no partying with A-listers, though he did receive a phone call from his kids.

Combs has been in jail pretrial since he was arrested in September, following a monthslong investigation that led to a grand jury indictment on charges of racketeering, sex trafficking, and transportation to engage in prostitution for allegedly causing victims and paid sex workers to cross state lines.

The Bad Boy Records founder faces anywhere from 15 years to life in prison on a federal indictment alleging that for decades, he used violence, threats, and drugs to coerce women into sexual performances, including at elaborately planned, dayslong parties called "freak offs."

Combs has pleaded not guilty, insisting through his lawyers that the sex was consensual and that his accusers have financial motives to implicate him. His next court date is Wednesday.

And more criminal charges may be coming, as prosecutors have said grand jurors are weighing a new indictment that could include allegations of obstruction of justice. Prosecutors allege that Combs has used phone accounts belonging to other people held at the jail to contact family members and associates and enlist them to plant negative stories about his accusers and funnel payments to a witness.

They also say agents recovered three AR-15 rifles with defaced serial numbers when search warrants were executed in March at Combs' homes in Miami and Los Angeles and at a Florida airport. And in September, when Combs was arrested at the Park Hyatt, a five-star hotel in midtown Manhattan, they recovered bags of pink powder that prosecutors said in September they believed contained ecstasy and other drugs. Prosecutors have not revealed the results of a drug test they said was conducted in September.

Since his arrest, Combs has made three unsuccessful attempts to be released on bail ahead of his criminal trial, which is scheduled for May 5.

"No condition or combination of conditions will reasonably assure the safety of the community," including of witnesses and prospective jurors, US District Judge Arun Subramanian wrote in the most recent bail denial, issued the day before Thanksgiving.

An avalanche of lawsuits

Just two weeks after Combs was arrested and subsequently locked up at the Brooklyn jail, the Texas-based attorney Tony Buzbee held a press conference to announce that his firm was representing 120 people accusing Combs of sexual misconduct.

"We are going to follow this evidence wherever it takes us. We will find the silent accomplices. We will expose the enablers who enabled this conduct behind closed doors," Buzbee said of his legal offensive.

Since Ventura's bombshell November 2023 lawsuit, more than 30 civil lawsuits have been filed accusing Combs of sexual abuse, including about 20 from Buzbee's clients, all listed as John Doe or Jane Doe.

"It feels really good to know he's behind bars," Adria English, who is not a Buzbee client, told BI. She worked as a dancer at Combs' famous white parties and filed a lawsuit in July accusing him of sex trafficking. "What we're having to speak of already sounds like we're lying — it already sounds like a movie because it's so horrible," she said. "It's so disgusting."

Attorneys for Combs pointed BI to a statement previously released in response to English's lawsuit, saying in part: "No matter how many lawsuits are filed it won't change the fact that Mr. Combs has never sexually assaulted, or sex trafficked anyone."

The "I'll Be Missing You" rapper has been accused by both men and women of rape, sexual assault, and lacing drinks with drugs. Over half a dozen of the lawsuits allege the abuse of boys and girls between 10 and 17 years old. Four lawsuits allege that sexual attacks happened at Combs' famed A-list white parties throughout the late 1990s and early 2000s, and two of those four lawsuits allege teenagers were victimized.

Timeline of events

Earlier this month, a woman accused the rapper Jay-Z, whose real name is Shawn Carter, of raping her with Combs when she was 13 years old at a party following the 2000 MTV Video Music Awards. An unnamed plaintiff originally filed the lawsuit in October, identifying Carter only as "Celebrity A."

Carter, in a statement through the X account of his entertainment company, Roc Nation, denied the allegations, calling them "heinous" and accusing Buzbee, the plaintiff's lawyer, of trying to "blackmail" him.

Attorneys for Combs continue to call all the lawsuits brought by Buzbee publicity grabs.

"Mr. Buzbee's lawsuit against Jay-Z and Mr. Combs and the recent extortion lawsuit Jay-Z brought against Mr. Buzbee exposes Mr. Buzbee's barrage of lawsuits against Mr. Combs for what they are: shameless publicity stunts, designed to extract payments from celebrities who fear having lies spread about them, just as lies have been spread about Mr. Combs," attorneys for Combs told BI Thursday.

The accuser in the lawsuit filed against Combs and Carter said in a recent interview with NBC News that there were some inconsistencies in her story but that she stood by the allegations.

Combs' lawyers are challenging the claims in at least seven lawsuits, which are ongoing. He has not responded in court to the lawsuits brought by Buzbee, which were all filed after his arrest.

A Los Angeles entertainment attorney, Camron Dowlatshahi, who's not involved in the lawsuits against Combs, told BI that though the rapper is still considered wealthy, litigating each of these cases through trial and potentially being exposed to multimillion-dollar judgments "does not seem prudent."

"Each of the lawsuits piggy-back on the other, and witnesses will be plenty," Dowlatshahi, a partner at the law firm Mills Sadat Dowlat, said.

Dowlatshahi said that lawsuits typically settle before trial and that he anticipated the same in Combs' case.

"Diddy will have to be strategic, however, in which cases he settles first and for how much," Dowlatshahi said.

 

Down with Diddy's empire

 

As the allegations against Combs have piled up, so have his legal bills.

Combs was once estimated to be worth $820 million, according to Forbes. He'd created an assortment of lucrative revenue drivers that contributed to regular eight-figure annual paydays, including a deal with Diageo; his lifestyle brand, Sean John; a record label; and a music catalog.

One by one, those income streams have dried up.

When the civil lawsuits started, Combs was already engaged in a legal back-and-forth with Diageo, his most bankable partner.

Combs signed with the liquor giant in 2007, agreeing to be the face of Cîroc vodka in exchange for a cut of sales. The partnership became one of the most lucrative celebrity liquor deals in history, expanding further when Combs and Diageo launched DeLeón, a co-owned tequila line. Over 15 years, the company paid him nearly $1 billion, Forbes reported.

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While Combs originally sued Diageo in May 2023, alleging the company did not support his ventures, the mounting sexual abuse lawsuits did him in, in the end.

"Mr. Combs is well-aware that these lawsuits make it impossible for him to continue to be the 'face' of anything," Diageo lawyers wrote in a letter to a judge in December 2023.

By January, the matter was resolved. Combs received $200 million for his stake in DeLeón tequila and not a penny for his longtime work with Cîroc.

 

 

It's a similar story for his other ventures.

Combs' lifestyle company, Sean John, had already slipped: In 2016, he sold a majority stake in the business, which at that point included fragrances and furnishings, to Global Brands Group for $70 million, Forbes reported. Just five years later, Global Brands Group filed for Chapter 11 bankruptcy protection, and Combs bought back the business for $7.55 million, just over 10% of what it was once worth.

The clothing line's website has gone defunct, its Instagram scrapped, and it is no longer sold at Macy's, once the exclusive home of the brand's sportswear line — and one of its last remaining retailers. The department store, which was accused by one of Buzbee's clients of covering up a 2008 sexual attack by Combs, did not comment on whether the removal of his Sean John line had to do with the compounding lawsuits. Macy's didn't respond to the allegations of covering up a sexual assault in court or to a request for comment about them from BI.

The disintegration of Combs' entertainment businesses, though, was a direct reaction to his mounting legal problems.

Soon after Ventura filed her lawsuit, Combs stepped down as chair of Revolt, the cable network and media company he cofounded. By June, he'd given up his stake. A Hulu reality show that was supposed to follow Combs and his family was scrapped. Any chance of his being able to cash out and sell his music catalog is slim.

"There are so many lost opportunities," Clayton Durant, a professor who teaches music business at Long Island University's Roc Nation School, told BI in October. "There is no way a brand is touching Diddy — probably forever."

With no moneymaking on the table, Combs has taken to trying to sell the assets he does have.

Earlier this year, he listed his Los Angeles mansion in the tony Holmby Hills for $61.5 million. His private jet, LoveAir, is also listed for sale, and while he awaits a buyer, he's been renting it out.

It's not clear how much use he will have for it anyway, at least in the near future.

On the eve of Thanksgiving, Combs lost his third application to be freed on $50 million bail.

Subramanian ordered that he remain held pending his May 5 trial, citing the rap mogul's history of violence and of contacting and threatening prospective witnesses.

"Diddy's been the ultimate puppet master for the last 30 years, and people wanted to say something … they've been too afraid," English, the dancer who accused Combs in a lawsuit of sex trafficking, told BI. "But now because of the raids, everybody's about to be exposed, regardless, so it's going to come out."