The first week of Sean “Diddy” Combs’ criminal sex-trafficking and racketeering conspiracy trial began with Casandra “Cassie” Ventura giving graphic and explicit testimony about the “humiliating” freak-offs she claimed she was made to endure over her decade-long relationship with Combs.
The sexual encounters are at the center of the criminal charges against Combs. Ventura spent more than 20 hours recounting to Southern District of New York prosecutors and Combs’ attorneys embarrassing and graphic details about freak-offs that allegedly began early on in the R&B singer’s romance with her older Bad Boy Records label boss.
“He brought the concept to me when I was 22, and I would do absolutely anything for him, and I did,” Ventura told the courtroom. “And it never stopped our whole relationship. And it was expected of me, and it made me feel horrible about myself.”
But the defense painted Ventura as a willing participant in the couple’s unorthodox sex life, displaying several messages where Ventura told Combs that she was open to the days-long sexual encounters. “I don’t want to freak off for a last time,” Ventura wrote in a message to Combs in September 2012. “I want it to be [the] first time for the rest of our lives.”
Throughout the first week, the one-time billionaire was actively involved in his case’s legal strategy, feverishly jotting down notes on a legal pad, passing over sticky notes to his attorneys, and shaking his head at the narrative prosecutors put forth.
While he maintained a neutral expression throughout much of Ventura’s testimony, he scowled at male escort Daniel Phillip, who told jurors he was concerned for Ventura’s well-being after he saw Combs hurl a liquor bottle in her direction. Phillip testified he saw Combs drag Ventura back into a bedroom by her hair during a freak-off because she asked Combs to wait a minute when he beckoned her. Midway through Phillip’s sexually explicit testimony, Combs’ three teenage daughters briefly left the courtroom before re-entering to grab their items and leave for the rest of the day.
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Combs is facing 15 years to life in prison if convicted of the five federal charges against him. He has pleaded not guilty and had been working to secure his release as soon as possible — rejecting a plea deal and moving for a speedy trial. (Earlier this week, Rolling Stone confirmed that several Combs allies have already laid the groundwork with President Trump officials for a possible pardon if Combs is convicted.)
The high-profile trial, which is expected to last seven more weeks, brought out a crowd of more than 100 people, as members of the press, lawyers, Combs supporters wearing “Free Diddy” T-shirts, content creators, and podcasters, including Rotten Mango’s Stephanie Soo and Fresh and Fit’s Myron Gaines, camped out overnight outside of the Manhattan federal courthouse in hopes of getting inside the courtroom.
Here are the key moments from the trial’s first week:
Cassie Testifies
The government’s star witness strode confidently into the courtroom on Tuesday morning, facing the man she claimed essentially turned her into a “sex worker.”
The so-called “freak-offs” are at the heart of the sex-trafficking and transportation to engage in prostitution charges against Combs, as prosecutors allege that Combs forced his younger girlfriend Ventura to have sex with hired male escorts through “force, fraud, and coercion.”
Over four days of direct testimony and grueling cross-examination, Ventura only cried twice when explaining the anguish she suffered as a result of being allegedly forced into freak-offs with dozens of strangers. “I’d give that money back if it meant I never had to have freak-offs,” Ventura said through tears about her $20 million settlement with Combs. “If I never had to have freak-offs, I would have agency and autonomy. I wouldn’t have to work so hard to get it back.”
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Ventura alleged that after entering into a relationship with Combs as a “naive” and sexually inexperienced 21-year-old in 2007 — shortly after signing to Combs’ record label Bad Boy Records — the music executive opened her up to a different kind of world. Gradually, Ventura alleged that her one-time promising music career took a detrimental backseat to constantly preparing and recovering from the days-long, drug-fueled freak-offs.
Remaining calm and poised, Ventura gave graphic details of what Combs expected during the sexual encounters. Combs “controlled” and “choreographed” everything surrounding the freak-offs, Ventura testified, even down to demanding Ventura have a fresh bikini wax, her nails painted white, and approving the lingerie she’d be wearing.
The pair always took Ecstasy or MDMA beforehand, Ventura alleged, and Combs would direct Ventura and the male escort to perform erotic acts leading up to intercourse. The sessions almost always began, Ventura said, by rubbing baby oil on her body until she was “glistening,” going through 10 bottles a night.
The intense sexual encounters would last until Combs determined they were over, Ventura testified, and that she paid the male escorts thousands of dollars in cash after sex, which Combs provided.
While Ventura said she tried to gently broach the topic of not wanting to do freak-offs, she testified that she was fearful of Combs’ flashes of rage and physical beatings, which occurred inside and outside of the sexual encounters. “I worried for my safety; I worried for my career,” Ventura said, explaining why she was scared of telling Combs no. “But I also was in love with him, so I worried that he wouldn’t want to be with me anymore.”
“I’m Always Ready to Freak-Off” Texts
When Ventura began cooperating with Southern District of New York prosecutors, she handed over several electronic devices, including iPads, cell phones, and computers, that contained thousands of texts and emails between the former couple.
Defense attorney Anna Estevao pulled up numerous emails and text exchanges where Ventura talks in an explicit sexual nature about freak-offs and seemingly expresses an openness to continue the sexual encounters. “I’m always ready to freak off,” Ventura wrote in one message to Combs in August 2009.
“I don’t want a freak-off for one last time; I want it to be the first time for the rest of our lives,” Ventura told Combs in 2012.
Estevao questioned why Ventura directly never said no to Combs when they began to arrange for a freak-off. She also suggested Ventura was an “insanely” jealous girlfriend, desperate to remain in a relationship with the high-powered Combs by any means.
“You participated in the freak-offs because you wanted to make him happy, right,” Estevao asked Ventura.
“Part of the reason, yeah,” she replied.
“You knew that this was the kind of sex that he wanted to have, right?” Estevao followed up. “And you believed that you were special in his life because you were able to give him that, right?”
Yet, some emails and messages seem to show Ventura gently pushing back on the idea of continuing freak-offs, expressing concern that that was the only aspect of their relationship. “The last time was a mistake, but since has made me feel a little dirty and grimy as opposed to sensual and spontaneous,” Ventura wrote Combs in December 2009.
“That’s the only reason why I go back and forth in my mind with wanting and not wanting to do it. When we used to freak-off when we were so in love, there were no questions asked, it felt right, like it literally made sense for the next step in our sex life together. I get nervous that I’m just becoming the girlfriend that you get your fantasies off with and that’s it. I don’t get the other part… anymore at least.”
Male Escorts with Criminal History
During her direct examination, Ventura identified at least a dozen male escorts that she said were frequently used in the “hundreds” of freak-offs she and Combs had throughout their decade-long relationship.
As she confirmed the identity of the men — some of whom allegedly traveled across the United States to meet up for the sexual encounters — she identified a man she knew as “Jonathan,” who was frequently used in Miami.
During her cross-examination, Ventura said the couple stopped using the male escort, whose full name is Jonathan Oddi, after she caught him secretly recording one of the sexual encounters. “You understood that Mr. Combs spent a great deal of time [and] money to make sure that that video went away, right,” Estevao asked.
The exchange confirmed a long-circulating allegation from Oddi, who was arrested in May 2018 for ranting against President Donald Trump and opening fire on police at Trump’s National Doral golf club in Miami. During his arrest, Oddi claimed that he was Combs and Ventura’s “sex slave,” giving details of freak-offs that he was involved in. But his seemingly fantastical claims were largely dismissed at the time — until Ventura’s lawsuit was filed.
Ventura also confirmed the identity of a man named “Ash,” whom she said she hired through the escort service Cowboys 4 Angels. The photo of Ash displayed on the screen in court resembled Ash Armand (real name Akshaya Kubiak), who was part of the Showtime reality show Gigolos, which followed the men who worked for the escort company.
In July 2020, Kubiak was arrested for beating to death Herleen Dulai, claiming he took psychedelic mushrooms and “temporarily lost my mind.” He pleaded guilty to voluntary manslaughter and mayhem and is currently serving an eight-to-20-year sentence in a Nevada prison.
In an interview with Rolling Stone from prison in January 2024 — before his name was publicly connected to Ventura and Combs — Kubiak confirmed he had met the couple at a party but denied being hired for freak-offs. “I’ve always been super respectful towards my clients,” he said, uncomfortable discussing the topic further. “It just all becomes tricky once the privacy is violated. Nobody will feel comfortable using the nature of the business.” (Rolling Stone was unable to reach Kubiak for further comment this week.)
Baby Oil and Pink Ketamine Found In Combs’ Hotel Room After Arrest
Following Combs’ arrest at the Park Hyatt Hotel last September, special agents conducted a sweep of his hotel room. Homeland Security Investigations special agent Yasin Binda testified that agents found numerous bottles of Johnson’s baby oil and Astroglide lubricant stashed around the hotel suite.
Several bottles were packed into a large Ziploc baggie inside a hallway closet, while others were found inside Combs’ nightstand table. A cluster of five bottles of baby oil and lube were neatly arranged at the bottom of Combs’ bathtub.
Special agent Binda also said that a Clonazepam prescription for “Frank Black” — a pseudonym that Ventura testified that Combs often used — was also found in Combs’ room, as well as two baggies of a pink powder that tested positive for ketamine and MDMA. A black fanny pack was slung over the edge of the bed was discovered to contain $9,000 in “bulk” cash, which was seized during the hotel search.
Combs’ lead defense attorney, Marc Agnifilo, previously told the court that Combs was coming to trial as a changed man and had previously sought out professional help by going to rehab years before addressing his substance use issues. “He has done tremendous things to try to change as a person since then,” Agnifilo told a judge shortly after Combs’ arrest last September. “He’s not the same person he was then.”
“It’s bullshit,” “Nathan,” a sex worker who claimed he was hired for several of Combs’ freak-offs, told Rolling Stone as part of a recent investigation into Combs’ behavior following his split from Ventura. “He’s not reformed. He just wanted to get out of jail. He’s the same person.”
Prosecutors did not link the bottles of baby oil, drugs, and cash to any specific allegation. However, as Rolling Stone reported, Combs had a woman staying with him at the hotel room.(On Friday, Combs’ attorney Teny Geragos confirmed a woman was sharing the room with him.)
Combs Grows Frustrated
Combs was animated during Ventura’s cross-examination, appearing somewhat frustrated with the tedious, slow pace that his attorney was taking when quizzing Ventura.
He took feverish notes, jumped up to look at the evidence screen, handed several sticky notes to his attorneys, and during a brief break towards the end of the day, clasped his hands in a pleading motion to Estevao, who was questioning Ventura.
When they resumed, Estevao focused on a long text exchange between Combs and Ventura right before the March 2016 freak-off, where Ventura appeared to be the one to propose a freak-off that day. Combs was seen nodding his head in approval as Ventura confirmed what she had texted.
Following Ventura’s cross-examination, Combs’ mood drastically shifted. He was all smiles and hugged Estevao at least twice, appearing confident the cross had been successful.
The Week Ahead
At the close of Friday’s proceedings, former Danity Kane and Diddy-Dirty Money singer Dawn Richard entered the courtroom, avoiding eye contact with Combs.
When Richard mistakenly said the wrong color of Combs’ sweater — white instead of cream — while pointing out Combs for the court, he teasingly put up both of his hands to identify himself.
Richard testified she had “never seen” anything like one instance of alleged physical violence where she testified Combs physically abused Ventura in 2009 over a batch of eggs. “He came downstairs screaming, belligerent, asking where his food was, and proceeded to hit her over the head, kicked her and beat her to the ground in front of us,” Richard told jurors. (Richard said her fellow Diddy-Dirty Money bandmate Kalenna Harper was present for the alleged assault.)
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Richard is expected to continue testifying on Monday. Ventura’s mother and Kerry Morgan, Ventura’s former best friend of 17 years, are also expected to testify next week.
Morgan has been mentioned several times throughout the first week of trial. Ventura alleged Morgan was present for many incidents involving Combs. Ventura testified that their friendship ended when Combs allegedly struck Morgan over the head with a wooden hanger in 2018.
