Sean 'Diddy' Combs trial updates: Cassie Ventura breaks down as testimony concludes

The hip-hop mogul is charged with sex trafficking and racketeering conspiracy.

Last Updated: May 19, 2025, 9:00 AM EDT

This story may contain accounts and descriptions of actual or alleged events that some readers may find disturbing.

Friday is day five in the trial of Sean Combs after the jury was seated.

May 13, 2025, 10:11 am

Sean Combs trial underway

The highly anticipated trial of hip-hop mogul Sean "Diddy" Combs is underway. Combs has been accused of sex trafficking by force, transportation to engage in prostitution, and racketeering conspiracy as part of a blockbuster federal indictment originally filed in September 2024. He later faced two additional superseding indictments. Combs has pleaded not guilty to all of the charges.

Combs is accused of being the ringleader of an alleged enterprise that "abused, threatened and coerced women" into prolonged, drug-fueled sexual orgies with male prostitutes, which he called "freak offs," and then threatened them into silence. Combs has said that all of the sex was consensual and that while his relationships sometimes involved domestic violence, he wasn't engaged in trafficking.

Combs' lawyer, Marc Agnifilo, said Combs was simply part of the swinger lifestyle and that he "vehemently denies the accusations made by the SDNY" and "looks forward to his day in court."

May 13, 2025, 2:41 PM EDT

Cassie Ventura breaks down on witness stand amid 'freak offs' testimony

Cassie Ventura broke down on the witness stand as she described her participation in so-called "freak offs."

Ventura said she had just turned 22 when Sean Combs first proposed these alleged marathon sex performances with male prostitutes that she said eventually “became almost weekly.” She said it would be impossible to remember participating in all of them.

The average length of a freak off was two or three days, Ventura said, the entire time during which she was awake, fueled by ecstasy, molly and cocaine she said was given to her by Combs.

“Who decided when a freak off was over?” prosecutor Emily Johnson asked.

“Ultimately that would be Sean,” Ventura responded.

“Did you want to participate in every freak off?” Johnson asked.

“No,” Ventura answered. “I felt like it was all I was good for. It was disgusting. I felt humiliated. I didn’t have the words for how horrible I really felt.”

If she refused to participate, Combs “would be violent with me,” according to Ventura.

“His look would just change over. He would become a different person and I didn’t know what was going to happen,” Ventura said.

When Johnson asked if there was any part of the freak off that she enjoyed, Ventura began to sob. She grabbed a tissue and, through tears, said “I thought it was the only time I could get.”

The first freak-off occurred at one of the homes Combs was renting in Los Angeles, Ventura testified. The jury was shown a photo of the male escort who participated. Ventura said she did not remember his name. She said she wore “really high platform shoes” and a masquerade mask at the freak off.

“Every freak off was directed by Sean. He knew specifically where he wanted everyone to be, the lighting,” Ventura said.

The case against Combs also involves those around him. Johnson asked Ventura about associates Toni Fletcher and Kristina Khorram, and security guards named Fahim and Uncle Paulie.

Ventura testified that she recalled seeing guns in several of Combs’ properties, “just laid out.”

She recalled an evening when, she said, one of Combs' employees allegedly told Combs that record executive Suge Knight was nearby. Combs and others then donned black clothing and guns, according to Ventura's testimony.

“I was crying, I was screaming. Like, please don’t do anything stupid,” Ventura testified.

May 13, 2025, 1:15 PM EDT

Cassie Ventura says she 'began to experience a different side' of Combs as relationship progressed

As her relationship with Sean Combs continued, Cassie Ventura told the jury “I began to experience a different side of him, which was his abusive side. But there was still love there.”

She described worrying about Combs' moods. “Make the wrong face and the next thing I knew I was getting hit in the face,” she testified.

Members of Combs' security staff “kept an eye on me,” Ventura said, and Combs would constantly call if she ignored him. At the same time, Ventura said she would get “insanely jealous” when she saw Combs with other women.

Sean "Diddy" Combs' former girlfriend Casandra "Cassie" Ventura is sworn in as a prosecution witness at his sex trafficking trial in New York City, May 13, 2025 in this courtroom sketch.
Jane Rosenberg/Reuters

“I was insanely jealous but also super-young, didn’t get it at all. Young and jealous,” she testified. “I didn’t get that he was him, as he would say: 'I’m Puff Daddy and Puff Daddy has many women.’”

Ventura described moving to Los Angeles and living in apartments Combs paid for, and what she described as the “stomach in knots” moments when he would drop by unannounced, not knowing if he was angry.

Though Ventura's recording contract with Bad Boy Records called for ten albums, she released only one. “If you’re not releasing music you’re not doing your job so the career was stifled,” Ventura said.

“Why did you not release another album during this time?” prosecutor Emily Johnson asked.

“You’re asking me?” Ventura responded in jest. “Plainly, the freak offs became a job where there was no space to do anything else but to recover and just try to feel normal again.”

Ventura said the alleged sexual encounters with prostitutes typically lasted anywhere from 36 to 48 to 72 hours. The longest one lasted four days, she said.

Court is currently in the lunch break. Ventura’s testimony is expected to continue for the remainder of the day and beyond.

May 13, 2025, 12:44 PM EDT

Cassie Ventura says Combs controlled her life, their relationship

Ventura told the jury Combs controlled a lot of her life, from her career to the way she dressed. “And it just didn’t feel like I had much say in it being super young, naïve, people-pleaser. I didn’t know if he would be upset enough to be violent or if he would write me off and not want to be with me at all,” Ventura testified.

If she refused Combs, Ventura said “it was always in the back of my mind that I would somehow be hurt.” Over time, she said “there were blackmail materials.”

Sean "Diddy" Combs' watches as his former girlfriend Casandra "Cassie" Ventura is sworn in as a prosecution witness at his sex trafficking trial in New York City, May 13, 2025 in this courtroom sketch.
Jane Rosenberg/Reuters

“I think I was just really confused at the time, and young, new artist, just didn’t know the lay of the land when it came to things like that. In my confusion just kind of cried and ran off,” Ventura testified. “I just wasn’t familiar with having an executive or anybody pay attention to me or be that forward at that point. Pretty naïve, I would say.”

Though 17 years younger than Combs, Ventura said she "wanted to be around Sean for the same reasons as everyone else at the time. He’s just this exciting and entertaining fun guy that just also happened to have my career in his hands.”

She testified that Combs introduced her to oral sex in a New York hotel room. “He basically taught me how,” she said.

“How did he introduce you to oral sex? “Johnson asked.

“He gave me oral sex,” Ventura responded.

The two first had intercourse on a boat Combs had rented on a trip to Miami, Ventura testified.

“I became one of his girlfriends,” Ventura said.

Combs listened passively to Ventura's testimony as he sat the defense table with his hands in his lap. Combs’ family listened in the second row.

Ventura’s husband, Alex Fine, is also in the courtroom.

May 13, 2025, 12:12 PM EDT

Cassie Ventura describes participating in 'freak offs' to please Combs

Cassie Ventura testified that she did not remember how the term “freak off” came about but she recalled Sean Combs proposed “this sexual encounter, that he called voyeurism, where he would watch me in intercourse, sexual activity with another man” within the first year of their relationship.

“I just remember my stomach falling, just the nervousness. I think I was 22 at the time, I didn’t have a concept to how that would be a turn-on but I also felt a sense of responsibility, him sharing that with me,” Ventura testified. “I wanted to make him happy.”

In soft-spoken, sometimes halting testimony interrupted by deep breaths, Ventura said the freak offs occurred so often that “eventually it became a job for me” to set them up.

After the first one, Ventura said her willingness to participate changed.

“Pretty quickly over time I knew it wasn’t something I wanted to be doing, especially how frequently. But I was in love and wanting to make him happy,” Ventura said. "I didn’t feel like I had much of a choice, didn’t really know what 'no' could turn into.”

Ventura alleged violent arguments with Combs that she said “would usually result in some physical abuse.”

“He would bash my head, knock me over, drag me, kick me, stomp me in the head when I was down,” Ventura testified.

“How frequently was Sean physical with you during your relationship?” prosecutor Emily Johnson asked.

“Too frequently,” Ventura responded.

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