Sean ‘Diddy’ Combs and the rise of his ‘criminal enterprise’

The most honest thing Sean Combs may have ever done was name his record label “Bad Boy.”

Although 54-year-old Combs – aka Puff Daddy, aka Puffy, aka P. Diddy, Diddy and Love – has been orchestrating a lot more than just braggadocious “bad” behavior during the intervening decades, according to a federal indictment unsealed Tuesday. Instead, it charges, he’s been the veritable architect and leader of a “criminal enterprise” engaged in alleged arson, kidnapping, forced labor, bribery, obstruction of justice and sex trafficking.

It was that final accusation, laid out not in federal charging papers but in a series of damning lawsuits last year, that first revealed the growing cracks in the veneer of Combs’ carefully-curated reputation. He strenuously denied all wrongdoing. But the filings were quickly followed by a bicoastal raid on his properties amid a tight-lipped federal investigation, then the leaking of a violent video showing Diddy’s brutal beating at a hotel of then-girlfriend Cassie– the most high-profile victim to sue him.

The footage was proof that his denials had been false all along. Combs tried a weak filmed mea culpa and apologized on Instagram, staying largely and uncharacteristically out of public view despite a few other presumed attempts at reputation rehab: two lukewarm family-centric posts on the same social media platform amid occasional statements from lawyers.

Those efforts did nothing to stem the tide of public embarrassments. Howard University revoked the honorary degree of which he’d been so proud. The mayor of New York asked Combs to return the key to the city. Even Miami Beach canceled its annual Sean Diddy Combs Day.

And now, exactly three years after Combs applauded the MeToo movement in a September 2021 magazine profile – and just one year after performing a medley of his hits to accept the Global Icon Award at the VMAs – he’s been arrested for a litany of jaw-dropping alleged offenses that include violent crimes against women. He was taken into custody in the lobby of a Manhattan hotel, a five-star setting in the city whose high society he presided over for years.

Federal prosecutors on Tuesday were pushing in court for detainment until trial – the prospect of drab prison scrubs a world away from Diddy’s years of flashy fashion and his legendary Labor Day Hamptons White Parties.

Everything that’s happening with Diddy right now, however, is a far cry from the teflon career he crafted for himself; he’s previously dodged prison time for charges related to everything from illegal gun possession to fatal concert stampedes. But the Combs depicted in the indictment – one who “abused, threatened and coerced … to fulfill his sexual desires, protect his reputation and conceal his conduct” – may have a harder time wriggling away from the long grasp of the law.

His public fame began muting last November, when three separate women filed lawsuits against Combs in a single week, some of the allegations dating back decades. The actions were taken before the expiration of New York’s Adult Survivors Act, which provided a one-year window for the pursuit of litigation, regardless of when the abuse occurred.

Most shocking were the allegations made by his former partner of a decade, singer Casandra Ventura, known professionally as Cassie and almost 20 years Combs’ junior. The couple were in a high-profile relationship for years until their 2018 breakup sparked a frenzy of headlines and gossip.

Combs settled the suit within a day – but not before the publication of Cassie’s staggering allegations. Among them, the suit claimed that Combs had raped her “in her own home after she tried to leave him; Often punched, beat, kicked and stomped on Ms. Ventura, resulting in bruises, burst lips, black eyes and bleeding;” and introduced her “to a lifestyle of excessive alcohol and substance abuse and required her to procure illicit prescriptions to satisfy his own addictions.”

But that was just the tip of the iceberg. Cassie’s lawsuit shockingly claims Combs had another rapper’s car blown up after learning the musician was romantically interested in Cassie; forced her to engage in sex acts with male sex workers in sessions he called “freak offs” while masturbating and filming the encounters; and demanded she “carry his firearm in her purse just to make her uncomfortable and demonstrate how dangerous he is.”

Despite the settlement, Combs denied all wrongdoing outlined in Cassie’s filings and within the other lawsuits – though his legal woes were far from over.

In February, former employee Rodney ‘Lil Rod’ Jones filed a suit accusing Combs of sexual harassment and threats. Weeks later, federal agents raided Combs’ homes in Los Angeles and Miami — he wasn’t at home at the time, although his sons were.

Homeland Security Investigations New York said the March raid was part of an ongoing investigation but did not elaborate at the time; the mogul’s lawyers called the raids a “gross overuse of military level force.”

Tuesday’s indictment, however, revealed some of what authorities recovered in those raids: narcotics, three AR-15s with “defaced serial numbers,” ammunition, a drum magazine” and evidence aligning with the “freak offs” so graphically outlined in Cassie’s lawsuit.

Also recovered were “more than 1,000 bottles of baby oil and lubricant,” according to the indictment, which alleges that Combs “subjected victims to physical, emotional, and verbal abuse to cause the victims to engage in Freak Offs.

“Combs maintained control over his victims through, among other things, physical violence, promises of career opportunities, granting and threatening to withhold financial support, and by other coercive means, including tracking their whereabouts, dictating the victims’ appearance, monitoring their medical records, controlling their housing, and supplying them with controlled substances.”

The day after the raid, authorities arrested a 25-year-old former college basketball player, Brendan Paul, who’d been named in ‘Lil Rod’ Jones’ court filings as an alleged drug mule for the superstar.

Then, in May, CNN published CCTV footage that it had obtained from March 2016 showing Combs chasinge Cassie down the corridor of a Los Angeles hotel before punching and kicking her near the elevators.

When confronted with that evidence, Combs finally apologized – calling his behavior “inexcusable” in a social media post, claiming to take “full responsibility for his actions in the video” and asking “God for his mercy and grace.” He said he sought professional help and went to therapy and rehab in the aftermath of the 2016 incident.

“It’s so difficult to reflect on the darkest times in your life, but sometimes you got to do that,” he said in a social media post. ”I was f***ed up – I hit rock bottom – but I make no excuses. My behavior on that video is inexcusable.”

Combs had already stepped down as chairman of his television company, Revolt, but the violent footage was sounding the death knell for some other feathers in his cap. The month after its release, Howard University – the historic black institution he’d attended before dropping out to pursue his music career – revoked the honorary degree it conferred ten years earlier, also returning Diddy’s donation money and disbanding a scholarship program in his name.

A decade after a humbled Combs stood proudly on the Howard graduation stage, accepting the degree in front of friends and family, the school issued a statement calling his behavior in the video “so fundamentally incompatible with Howard University’s core values and beliefs that he is deemed no longer worthy to hold the institution’s highest honor.”

The same month, New York City Mayor Eric Adams asked Combs to return the keys to the city and rescinded the honor he’d bestowed not even one year earlier, in September 2023, around the same time the singer performed at the VMAs and released his latest studio album.

The mayor and city commission of Miami Beach also in June 2024 revoked honors and recognition – canceling Sean Diddy Combs Day, which had been implemented on October 13 eight years earlier by the city’s then-mayor. They determined the designation was “no longer in harmony with the City’s values of safety, community well-being, and respect.”

Combs himself was laying low throughout all of this. He was pictured looking stone-faced near his Florida home in the weeks after the March raid, but his most well-known – and infamous – appearance this year was on that CCTV footage.

Until this week.

Now the courtroom sketches of Combs appearing before a New York judge are already usurping the more iconic images of his bedazzled rapper lifestyle. One of his raided homes, a 13-room mansion in Beverly Hills, is on the market for $61.5 million, put up for sale the week before his arrest.

Combs is fighting for his freedom, not just his business interest or his reputation. And that battle suffered a great loss on Tuesday when the judge denied his bail, ordering the rapper to remain in federal custody while awaiting trial on racketeering and sex trafficking charges.

Combs’ lawyer said he intends to appeal the decision on Wednesday, and there’s been no word directly from remanded Combs. For all his bluster and bravado, he’s shown no interest in real prison time in the past; when he was found not guilty in March 2001 of gun and bribery charges, Combs was visibly shaking before the verdict was read.

Legions of fans thronged the courtroom and beyond during that trial, which stemmed from a 1999 nightclub shooting that occurred while Combs was with Jennifer Lopez, both of them arguably at the height of their fame.

Fans “threw open the windows” of the courthouse upon his acquittal, chanting his name and ‘Leave him alone,’” The New York Times reported at the time.

That was a different era, however, and a very different, still serious set of charges; Diddy was years from being accused of directing a criminal enterprise over decades of drugging and assaulting women, leaving injuries that took weeks and months to heal.

This time, he’s facing a prosecution that represents him as being a criminal mastermind who “used the Combs Business, including certain employees, to carry out, facilitate and cover up his abuse and commercial sex. Those employees – including security staff, household staff, personal assistants and high-ranking supervisors – and other close associates acted as Combs’ intermediaries, and their conduct was facilitated and assisted by Combs’ control of the Combs business.”

The rapper orchestrated and continued to carry out a campaign of terror against victims even after the most damning allegations came out against him last year, according to the indictment.

“Combs and members and associates of the Enterprise pressured witnesses and victims, including through attempted bribery, to stay silent and not report what they experienced or knew to law enforcement,” it states.

Still, though, the investigation persisted, gathering enough evidence against the impresario to land him in custody for what now seems to be an indeterminate amount of time.

Combs’ attorney, Marc Agnifilo, on Tuesday insisted his client was “an innocent man with nothing to hide.”

“Mr Combs is a fighter, he’s going to fight this to the end,” Agnifilo said outside of the federal courthouse.

Twenty-three years ago, Combs was celebrating the continued success of his release Bad Boy for Life and his third studio album, The Saga Continues.

Perhaps both titles marked another hint of honesty from Combs – and more than a little bit of foreshadowing.