Cassie spent two full days this week giving testimony in Sean “Diddy” Combs’ federal sex trafficking and racketeering trial, with Complex present to witness it all. We’ve heard plenty said about Cassandra Ventura and her alleged experiences with her ex-boyfriend of nearly eleven years, but Tuesday and Wednesday marked the first time people heard the story straight from her. Diddy has consistently denied all allegations against him. The music mogul faces charges of racketeering conspiracy, sex trafficking, and transportation to engage in prostitution.
Guided by prosecutor Emily Johnson’s questions, Ventura recounted her journey with Diddy from the very beginning – signing with his Bad Boy Records in early 2006 when she was just 19. She continued all the way through to her headline-making 2023 lawsuit against him and her motivation for appearing at this trial.
Throughout her testimony, she revealed a troubling portrait of more than a decade spent managing the temperament of a man who she claimed could become violent without warning; and the “hundreds” of occasions where she unwillingly participated in “freak-offs” — the sometimes multi-day, sleepless, drug-heavy sexual encounters involving Diddy and other men.
Sean Combs, according to Cassie’s account, transformed from record label boss to boyfriend to someone who dominated every facet of her existence. She testified that he wielded violence, blackmail, and his own assets, staff, and companies—along with Cassie’s feelings for him—to maintain this iron grip.
Her testimony delved deeply into the alleged “freak-offs,” which she claimed started within their relationship’s first year. She stated he expressed interest in voyeurism, wanting to watch her have sex with another man.
What she described was far more intricate than that simple explanation. Freak-offs, as Cassie portrayed them, were meticulously orchestrated events, with Diddy micromanaging every element: from the room lighting, to who touched whom and when, to dictating when the male escort was allowed to climax.
Cassie made it clear that from day one, she wasn’t interested in these freak-offs. She characterized them as an extension of the dominance Combs exerted over every other part of her life: her music choices, clothing style, hairstyle, even down to her nail polish color.
“He called all of the shots,” she stated plainly.
Combs, she alleged, was such a manipulator that he deliberately kept her recording music constantly not because he intended to release her work, but to keep her occupied with what she termed “busywork.” As long as she remained in his studios, surrounded by his people, music-making became, in her words, a method to “establish control over what I was doing every minute of the day.”
Photo by Kevin Mazur/WireImage/Getty According to her testimony, Diddy’s obsession with monitoring her whereabouts was practically never-ending. She described countless instances where, if she didn’t answer him right away, he would bombard her with calls and texts, dispatch staff to track her down—or just show up at her place unannounced.
One key method Diddy used to maintain his control over her was, Cassie claimed, through physical abuse. A significant portion of Wednesday’s testimony was devoted to the singer detailing numerous alleged attacks.
The domestic violence reportedly began very early in their relationship, following a dinner in New York City around 2007 or 2008. Cassie testified that she mentioned to a friend at dinner that Combs was flirting with another woman. Afterward in the car, she claimed Combs struck her on the side of her head—with the driver watching the whole thing.
“I didn’t understand why he was so angry,” she recalled.
But that, she testified, was nothing compared to what followed. She described an alleged attack in 2009 where Combs stomped on her face. When she tried to escape, she claimed his security caught her and brought her back. Diddy then allegedly forced her to stay at a hotel for about a week while her injuries healed.
She detailed several other alleged violent incidents: one where he burst into her hotel room, assaulted her, and hurled luggage at her. Another time he allegedly kicked her in the back hard enough to leave a massive bruise after discovering she was seeing Kid Cudi. The incident in Jamaica when he supposedly gave her a black eye, causing Cassie and her best friend to hide under a tractor for hours. A 2015 attack when, already recovering from a previous beating that left her with a black eye, he allegedly assaulted her again, leaving her huddled beneath a toilet trying to shield herself from his kicks. An incident before an OVO Fest when he allegedly threw her into a bed frame, leaving a permanent scar. And the time he allegedly struck her then-best friend in the head with a wooden hanger.
Then there was the assault everyone has seen: the one captured in the hallways of the Intercontinental Hotel in Century City on March 5, 2016. Ventura watched that footage on the stand, facing her alleged abuser, his family, his seven attorneys, and reporters from around the world.
She also provided important context. It happened, she explained, during a freak-off — which itself occurred just days before a premiere of a movie she appeared in, an event she was genuinely excited about.
“I never had an opportunity to enjoy the things I worked really hard on,” she explained. “If I pleased him with a freak-off, then my premiere would run smoothly.”
In the middle of the freak-off, she said, “I got hit by Sean and I had a black eye. I had my premiere and I didn’t want to mess it up.”
So she attempted to leave, which is what led to the scene that years later would end up on CNN and, eventually, screens across the world.
When asked how often she was violently thrown to the ground in the way shown on that tape, Ventura answered, “Too many times to count.”
A lot of Ventura’s testimony that was not about violence was about the freak-offs. She began with the very first one, which she said happened in Los Angeles. Combs, she said, provided ecstasy and instructed her to dress in high heels.
As she described it, Combs directed her and the escort to rub baby oil on each other, and then have sex while he watched. That happened at least twice.
Afterwards, she said, she felt “a mixture of dirty and confusion with [a feeling that] he’s really happy with me, so I did something right.”
Within weeks, he had proposed a second one. And then they kept going, to the point where freak-offs happened almost weekly for what she described as “a consistent amount of years.”
As mentioned, she said that the sessions could last for days, with Cassie awake the whole time. She testified that Diddy provided the drugs — molly, ecstasy, cocaine — that kept her awake. He would even, she alleged, tell her when to take them.
In her testimony, he would also be the one to say when the freak-offs would happen, and when they ended. He would also, she said, even insist that she participate in them when she was menstruating or had a UTI, the latter of which she said she had “sometimes back to back” as a result of the freak-offs.
When asked by the prosecutor what she enjoyed about the freak-offs, Cassie got choked up. She explained that the moments between sex with escorts, when she and Combs would retire to a separate room, was the only one-on-one time with him that she could get.
She also explained that she had been extremely young, and in love, when first presented with them.
“He brought the concept to me when I was 22 and would do anything for him,” she said on Wednesday. “And I did.”
Cassie explained that she often brought up—”gently,” she said, so as not to anger Diddy — the idea of wanting to stop the freak-offs. But he would be dismissive. And keeping them going was, after all, making him happy.
“When you love somebody, you don’t want to disappoint them,” Ventura explained.
While only Cassie, Diddy, and the escorts were, she said, present at the freak-offs, Cassie described the preparation as a family affair: Diddy’s assistants or security, she said, would often stock the room with baby oil, lubricants, and condoms, and would sometimes even bring the cash to pay the escorts.
Diddy, she testified, would sometimes record the sessions, saying that it was for him to view afterwards. But, she said, he quickly pivoted to using the potential release of the tapes as blackmail.
That threat hit Ventura hard, she explained.
“I would have to answer to my mother,” she said. “I feared for my career. I feared for my family.”
One of Cassie’s final in-person interactions with Diddy, she said, was in August, 2018, after they had broken up. Following what she called a “closure conversation” at dinner, where Combs was being nice and playful, they went to her house.
“And then,” she said bluntly, “he raped me in my living room.”
“I just remember crying and saying no, but it was very fast,” she continued. She said that the mogul’s eyes were black, and that he “wasn’t himself.”
“It was like somebody taking something from you,” she continued.
She was intimate with him one more time after the rape, after what she called “a really nice night that we never really had before.”
Toward the end of her testimony on Wednesday, Ventura broke down when recounting a particularly low point in early 2023, when she was feeling suicidal. She said that she “tried to walk out the front door [of her home] into traffic, and my husband would not let me.”
After that, she began writing down her experiences with Combs.
“I really wanted Sean to read the information. I wanted him to understand,” she explained through tears.
She continued crying while discussing how she realized the damage from the freak-offs came from “having to carry the shame that was painful to [Combs].”
She went on to reveal that she sent book chapters to Combs, asking for $30 million for the rights to the book. (About the amount, she explained “I picked a number that would alert him.”)
“I wanted to be compensated for the time, the pain, the many, many years of having to fix my life,” she testified.
The rest of the story is public knowledge from there: she filed her civil lawsuit in November 2023, and reached a $20 million settlement within just 24 hours.
As her testimony wrapped up, prosecutor Emily Johnson asked Cassie why she chose to take the stand in this trial.
“I can’t carry this anymore,” she confessed. “I can’t carry the shame, the guilt. I was guided to treat people like they were disposable.
“What’s right is right, what’s wrong is wrong,” she added. “I’m here to do the right thing.”
