Inside Diddy's Bad Boy empire of threats, violence and bribes. What court revelations expose
At its height, Sean "Diddy" Combs' Bad Boy Entertainment was a show business powerhouse, mixing music, video, fashion, liquor and style into a business that made Combs a billionaire.
Combs won praise for his visionary growth and brand management.
But federal prosecutors have another word for Bad Boy: a racketeering enterprise.
The federal trial in New York City includes an allegation that Combs was involved in mob family-style racketeering with coercion, kidnapping, threats and beatings done to cover up a pattern of sexual assaults, sex trafficking and prostitution.
The mogul has publicly and defiantly maintained his innocence even before his arrest last September.
Read more: Sean Combs' inner circle reveals a world of guns, abuse, kidnapping and death threats
The federal indictment alleges that Combs and his associates lured female victims, often under the pretense of a romantic relationship. Combs then allegedly used force, threats of force, coercion and controlled substances to get women to engage in sex acts with male prostitutes while he occasionally watched in gatherings that Combs referred to as 'freak-offs.' Combs gave the women ketamine, ecstasy and GHB to 'keep them obedient and compliant' during the performances, prosecutors say.
Combs' alleged 'criminal enterprise' threatened and abused women and utilized members of his enterprise to engage in sex trafficking, forced labor, interstate transportation for purposes of prostitution, coercion and enticement to engage in prostitution, narcotics offenses, kidnapping, arson, bribery and obstruction of justice, prosecutors said. In bringing so-called RICO charges, prosecutors in opening statements said Combs was helped by a cadre of company employees, security staff and aides. They allegedly helped organize the freak-offs and then covered up the incidents. Thus far, Combs is the only one facing criminal charges related to the investigation.
Have prosecutors made the case?
Prosecutors have so far called nearly 30 witnesses to the stand in Manhattan and are expected to finish up with witnesses this week.
They include three women who described graphic sexual assaults, including a woman the defense acknowledged was the key witness, Combs' onetime lover, Casandra "Cassie" Ventura. It was Ventura's lawsuit in 2023 that set off the unraveling of the Combs enterprise with its details of sex, violence and freak-offs.
His last former girlfriend, referred to only as Jane in court, described how the freak-offs and coerced sex continued despite the lawsuit and a raid by Homeland Security Investigations until his arrest.
She texted Combs pages of Ventura's lawsuit immediately after it was filed.
'I've been crying for three days and am under stress from reading all of this. I keep having nightmares about forced nights and all the times I felt like I couldn't say no. I feel like I'm reading my own sexual trauma,' she wrote, according to Legal Affairs and Trials.
Read more: 'Horrible and disgusting': Cassie's graphic testimony of abuse leaves Sean 'Diddy' Combs' fate hanging in balance
On another occasion, she said she texted his chief of staff about the threats he made, writing, 'He just threatened me about my sex tapes that he has of me on two phones. He said that he would expose me and send them to my child's father.'
Jane is one of three women whose testimony is at the center of the trial, the others being Ventura and a former employee testifying under the pseudonym Mia, who also testified she was sexually assaulted.
Under the Racketeer Influenced and Corrupt Organizations Act, known as RICO, there are 35 specific offenses, including kidnapping, murder, bribery and extortion, and federal prosecutors need to show a pattern involving at least two overt acts as part of a criminal enterprise.
Neama Rahmani, a former federal prosecutor, said that to prove RICO, the prosecution must show the existence of not just criminal activity but an actual criminal enterprise.
People typically think of the mob, street gangs or drug cartels. But any loose association of two or more people is enough, like Combs' entourage, she said.
They also have to show a pattern of racketeering or two or more RICO predicate acts over a 10-year period.
That's why the evidence of bribery, kidnapping, obstruction, witness tampering and prostitution is important to the prosecution's case, she said.
It will be up to jurors to determine if federal prosecutors proved the RICO charge.
R&B singer Ventura, who had a long relationship with Combs, was an early key witness in the prosecution's case.
Ventura testified she felt "trapped" in a cycle of physical and sexual abuse by him, and that the relationship involved 11 years of alleged beatings, sexual blackmail and a rape.
She claimed Combs threatened to leak videos of her sexual encounters with numerous male sex workers while drug-intoxicated and glistening with baby oil as he watched and orchestrated the freak-offs.
Read more: Sean 'Diddy' Combs faces sexual abuse, exploitation allegations from 120 people, including minors
One of those freak-offs led to an infamous hotel beating, Ventura testified. Video footage from that March 2016 night shows Combs punching and kicking Ventura as she cowers and tries to protect herself in front of an L.A. hotel elevator bank. He then drags her down the hall by her hooded sweatshirt toward their hotel room.
A second angle from another camera captures Combs throwing a vase toward her. She suffered bruising to her eye, a fat lip and a bruise that prosecutors showed was still visible during a movie premiere two days later, where she donned sunglasses and heavy makeup on the red carpet.
A cover-up then ensued, according to prosecutors. Ventura stated that the police visited her apartment. She answered a few of their questions, but told the jury she still wanted to protect Combs at the time.
'I would not say who I was talking about,' she told the jury. 'In that moment, I did not want to hurt him in that way. There was too much going on. It was a lot.'
Eddie Garcia, the InterContinental Hotel security guard, testified that Combs gave him a brown paper bag containing $100,000 in cash for the video.
Garcia said after his supervisor agreed to sell the video recording, he met with Combs, Combs' chief of staff Kristina Khorram and a bodyguard. After Garcia raised concerns about the police, he said Combs called Ventura on FaceTime, handed him the phone and told Ventura to tell Garcia that she also wanted the video "to go away." After that, Garcia said he took the money and split it with co-workers.
Read more: Accusing a pop superstar of sex trafficking: What R. Kelly case tells us about Sean 'Diddy' Combs
Capricorn Clark, a former assistant to Combs, recalled a 2011 violent incident with Combs.
Clark told jurors Combs forced her from her apartment at gunpoint to go with him to musician Kid Cudi's home in December 2011. Once there, Combs and Clark entered the empty house, and then Cudi, whose real name is Scott Mescudi, showed up. To avoid getting law enforcement involved, Clark testified, Combs ordered her to call Ventura, who was at that time Combs' ex-girlfirend, and said they need to convince Cudi not to snitch to the cops. "If you guys don't convince him of that, I'll kill all you m—,' Clark quoted Combs saying.
Cudi testified that his Porsche was later firebombed in his driveway with a Molotov cocktail.
Ventura wasn't Combs' only alleged sex crime victim. Mia, an assistant testifying under that name, described years of sexual abuse, rape and threats. Combs, she said, first sexually assaulted her at his 40th birthday party in New York in 2009, shortly after she began working for him. In the year that followed, she slept in a bedroom at his home, where she was not allowed to lock the door. Through tears, she testified he raped her. "I was frozen. I didn't react. I was terrified and confused and ashamed and scared." Another alleged attack occurred in a bedroom closet where she said Combs grabbed her head and forced her to perform oral sex on him.
Under cross-examination, she said she did not initially tell federal prosecutors that Combs sexually assaulted her and acknowledged sending Combs loving messages in the years after the alleged attacks.
Jane, his most recent ex-girlfriend, described how she endured drug-fueled sex marathons right up until the hip-hop titan's arrest.
Bryana Bongolan, a friend of Ventura, testified that Combs dangled her over a 17-story balcony and tossed her onto balcony furniture in September 2016.
'I will never forget him holding me on that balcony," she said as a defense lawyer challenged the date she provided with evidence of Combs being elsewhere at a hotel across the country.
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Throughout the trial, Combs has been visibly engaged, leaning forward, passing notes to his lawyers and even nodding so 'vigorously' in the direction of jurors, the judge threatened expulsion from the courtroom. Combs also has a history of speaking up when the legal chips are down. He testified in his own defense at his 2001 trial over charges he brandished a gun during a shooting in a Manhattan nightclub, leading to an acquittal. After CNN released damning video last year showing him kicking and dragging Ventura at the InterContinental, he responded within 48 hours, releasing a lengthy video apology, making 'no excuses.' He clearly likes to share his thoughts. 'I'm sure Sean Combs wants to testify. I'm also sure his lawyers are telling him that would be a terrible idea,' David Ring, a plaintiff's lawyer who represented Evgeniya Chernyshova, the Italian actress whose testimony led to Harvey Weinstein's rape conviction in California, tells Rolling Stone. 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'Or maybe they've been interviewed, but they weren't granted immunity, so they're in a holding pattern because they're not going to get up on the stand,' Adamson says. (Those involved could invoke their Fifth Amendment right to not testify.) 'There has to be a conspiracy, but the government doesn't have to charge the other co-conspirators,' Ring says. 'I doubt anyone else will be charged.' Ring says Combs' security, his assistants, the people who allegedly carried drugs for him, and those that set up the freak-offs could all qualify as co-conspirators without being charged. He adds that charging them could actually backfire. 'When people cut a deal and then they take the stand, it's fair game for the defense to question their credibility because, hey, they took a deal and got something in exchange for their testimony,' he says. Khorram, also known as K.K., started working for Combs in 2013 and became his longtime chief of staff. In a 2021 Facebook post, Combs called her his 'right hand,' claiming he couldn't 'function without her.' Prosecutors didn't name Khorram in their opening. Instead, they were general, saying Combs relied on his inner circle, including 'chiefs of staff,' to run 'all aspects of his life.' On June 5, prosecutors got more specific, dubbing Khorram, 38, an 'agent and co-conspirator.' Jurors have heard Khorram's name over and over. Ventura said she communicated with Khorram 'every day,' adding that Khorram knew Combs was physically abusive. She said Khorram reached out directly after the InterContinental incident to say Combs was looking for her. Indeed, it was on Khorram's seized devices that investigators found the photo IDs for the hotel security guards linked to the $100,000 'bribe' from Combs. One of the guards testified it was Khorram who called repeatedly and showed up in the hotel's lobby looking for him before the deal was brokered. For her part, Jane testified Khorram encouraged her to smuggle Ecstasy pills for Combs in her checked luggage. 'It's fine. I do it all the time,' Khorram allegedly said. Jane also claimed Khorram booked her travel for the so-called 'hotel nights.' 'Her name has come up so much during the trial, if she's not put on the stand, the jury will be wondering, 'Where's Kristina?' Adamson tells Rolling Stone. 'She could have some of the highest evidentiary value here … in terms of proving the alleged conspiracy.' On Friday, prosecutors hinted they would rest their case this week without calling Khorram. They listed their final witnesses as Combs' former assistant Brendan Paul, a law enforcement officer, and three summary witnesses. 'If she's not called, it could be she's too risky [and] that prosecutors are worried her testimony would cut favorably to Diddy,' Adamson says. 'Or it could be that they're not giving her immunity, and she has a Fifth Amendment right against self-incrimination.' Experts who spoke with Rolling Stone say that given Khorram's high-level position, it's also possible she's a target. 'Maybe she's been charged. and we don't know it, because it's sealed,' Adamson says. 'That's just in the range of possibilities – but less likely.' From the moment of Combs' arrest, his defense team has painted the government's case as a broad abuse of power, coming into his bedroom, scrutinizing his personal sex life, and deeming it as criminal. They've been open that Combs is polyamorous, engaged in 'kinky' sex, was a jealous lover, and part of a swingers' lifestyle. They also readily admitted there were episodes of domestic violence, particularly in Combs' decade-long relationship with Ventura. But they were adamant that Combs' conduct and perhaps taboo sexual preferences do not equate to the serious charges he's facing. 'Domestic violence is not sex trafficking,' Geragos said in her opening statement. That argument will likely be prominent as the defense presents its case later this week or early next week. Combs' defense team has also raised questions about his former girlfriends' roles in these 'toxic' dynamics. 'The alleged victims who will testify in this case are capable, strong, adult women,' Geragos said. 'They all had the personal responsibility and the freedom to make the choices that they made.' Combs' all-star defense team has also grilled witnesses on their motives, particularly those related to financial gain. They've elicited testimony from several of Combs' former employees who praised the mogul's brilliance and 'can't stop, won't stop' work ethic, suggesting that due to the nature of Combs' around-the-clock schedule, his personal life inherently meshed with his business duties. They said the blurred lines don't constitute conspiring to run a criminal enterprise. While those are just some of the defenses Combs' side has offered during the prosecution's case, his team has kept a tight lid on who he might call to the stand. They've only revealed they plan on calling Dr. Sasha Bardey, a psychiatrist, to rebut the testimony of government witness Dr. Dawn Hughes, who testified about sexual abuse, coercive control, and intimate partner violence. Shortly before the expected eight-week trial commenced, a long-whispered-about woman identified as Victim-3 vanished from the prosecutors' case. The woman first emerged in a second superseding indictment against Combs in March. Unlike Ventura and Jane, Victim-3 wasn't connected to a specific sex trafficking charge. Instead, she was mentioned under the racketeering conspiracy count. The government alleged Combs lured the woman into his orbit 'under the pretense of a romantic relationship and used physical violence, threats, financial control, and coercion to allegedly compel her to engage in commercial sex acts, known as 'freak-offs.'' In late April, just a few weeks before the trial's start, the woman agreed to testify under her real name. But, on the eve of the trial, prosecutors reported difficulties in contacting the woman and her attorney, later stating that she would no longer testify. The government would confirm Victim-3 as Gina, one of Combs' girlfriends who has been in an on-off relationship with him since around 2015. Her name has continually surfaced during the trial, with Ventura admitting that Gina was a source of contention in her decade-long relationship with Combs, a refrain echoed by Jane, who dated Combs from 2021 until his September arrest. One of Combs' former assistants, George Kaplan, alleged he once observed a fight between Combs and Gina, in which Combs hurled apples at her, and Gina later yelled to be let out of Combs' Miami mansion in the middle of the night. But prosecutors lost their bid to include a text conversation between Combs and his former head of security, who issued a dire warning to Combs that he could go to jail if word leaked about an apparent violent incident between the couple in October 2015 in Atlanta. 'If anyone called the police, the police is a 100 percent going to lock you,' the security member allegedly texted Combs. 'Even if she begs them not to, it's the law. So once they put the cuffs on you, your life and career is over.' It's still unclear if another alleged victim, Victim-5, will take the stand. Prosecutors haven't mentioned the person in any publicly filed documents, but Combs' defense attorneys objected to portions of their testimony in a heavily redacted filing. The judge ruled any testimony from the alleged victim had to be narrowly tailored. As Combs faces up to life in prison if convicted, he's also facing another legal crisis on the civil front. In the wake of Ventura's pivotal November 2023 filing, a tidal wave of more than 50 women and men have claimed the larger-than-life mogul abused and sexually preyed on them over three decades. While more than a dozen of the civil suits include accusations of sexual assault that overlap with SDNY prosecutors' timeframe of the alleged racketeering conspiracy — 2004 until 2024 — the deluge of filings has barely played a role in the criminal case. Only the testimonies of fashion designer Bryana 'Bana' Bongolan and former Bad Boy artist Dawn Richard have come into the trial so far. Although both women alleged sexual misconduct by Combs, prosecutors essentially used their testimonies to boost corroboration of Ventura's claims that Combs would unleash brutal attacks on her. Richard testified that on her first day recording the 2010 Diddy-Dirty Money album, Last Train to Paris, she saw Combs attempt to hit Ventura with a frying pan before dragging her to an upstairs bedroom by the hair because he was upset about how she was cooling his eggs. Richard was not permitted to discuss her separate personal claims against Combs, claiming he sexually harassed and groped her and once ordered one of his executives to lock her in a freezing car for hours after speaking back to Combs. Bongolan, who forged a close friendship with Ventura in 2015, claimed she saw the lengths to which Combs would go to attempt to control Ventura, incessantly blowing up her phone and monitoring her location. She said she routinely observed bruises on Ventura and allegedly saw Combs once hurl a knife in his girlfriend's direction after showing up to her apartment unprompted. But unlike Richard, Bongolan was able to testify more about her personal experiences with Combs. She claimed he once called himself the 'devil' and warned he 'could kill' her. She claimed the powerful music executive almost dangled her over Ventura's 17th-floor balcony, yelling, 'You know what the fuck you did!' The government used the alleged incident as evidence that Combs' abuse of Ventura was boundless, spreading to her closest friends when he flew into a rage. They also suggested it reinforced Ventura's fear of Combs and kept her trapped in the decade-long relationship. Best of Rolling Stone Sly and the Family Stone: 20 Essential Songs The 50 Greatest Eminem Songs All 274 of Taylor Swift's Songs, Ranked
