Diddy trial Day 2: Ex-girlfriend Cassie Ventura testifies about 'freak-offs'

NOTE: The following article contains disturbing details and video footage. Please read at your own discretion.

As the sex trafficking trial for Sean “Diddy” Combs enters its second day, Combs’ ex-girlfriend, Cassie Ventura, took the stand Tuesday.

Ventura is considered a star witness for the prosecution and her testimony is particularly valuable. Combs was captured on security video violently assaulting Ventura in a hotel hallway in 2016.

The video was obtained and distributed by CNN in May 2024, and showed Combs launching a brutal physical assault on Ventura in which he grabbed her by the back of the neck and threw her to the floor, before kicking her twice while she lay on the ground.

While giving testimony, Ventura became emotional at times and spoke about feeling the “disgusting” and “humiliated” by Combs’ control over her, particularly during his alleged days-long sex parties, where she says she was forced to have weekly sex with escorts while her boyfriend plied her with drugs, watched, recorded and orchestrated her behaviour.

Day 2

As an eight-month pregnant Ventura entered the court Tuesday, Combs turned in his chair to watch, reports the New York Times. She didn’t meet his gaze, looking straight ahead as she walked to the front of the room.

“There were violent arguments that would usually result in some sort of physical abuse. Dragging, different things of that nature,” she told the court, when asked by the prosecutors to describe her relationship with the rapper.

She testified that Combs would mash her head, drag her, kick her and stomp on her when she was down.

Asked how frequently Combs became violent with her, Ventura softly responded: “Too frequently.”

She was then asked about her role in Comb’s so-called “freak-offs” — the drug-fuelled, multi-day sex parties her ex allegedly orchestrated.

Ventura told the court the parties stemmed from Combs’ interest in voyeurism, and they would entail hiring an escort and “setting up this experience so that I could perform for Sean,” Ventura said.

Shown still images from the now-infamous 2016 security camera footage of Combs beating her at a Los Angeles hotel, Ventura said prior to the altercation, “We were having an encounter called a ‘freak-off’ and I was leaving there.”

She said, as a 22-year-old, she was “confused, nervous,” when Combs first started asking her to participate in the parties, but that she “also loved him very much.”

Ventura said she felt powerless and afraid to say no to her boyfriend, fearing retaliation in the form of violence or blackmail threats.

“I didn’t know what ‘no’ could be, or what ‘no’ could turn into,” she said. “Sean controlled a lot of my life, whether it was career, the way I dressed, everything, everything. I just didn’t have much say in it at the time.”

Elaborating on why she felt it was so difficult to refuse Combs’ demands, Ventura reiterated her fears of violence and blackmail videos from “freak-offs” being disseminated on the internet.

“Sean is a really polarizing person, also really charming,” she said. “It’s hard to really be able to decide in that moment what you need when he’s telling you what he wants. I just didn’t know. I didn’t know what would happen.”

The line of questioning then turned to Ventura’s history with Combs — when she was first signed to his Bad Boys record label in 2006, their first kiss and when they began dating.

She said her interactions with Combs were platonic at first. But then he kissed her during her 21st birthday trip to Las Vegas in the bathroom of his hotel suite. “I was just really confused at the time,” she said. “And young.”

After the Las Vegas trip, Ventura said, she was invited by Combs to hotels in New York where they’d talk about music projects and albums.

When asked what else happened at the hotels, Ventura, taking a moment to breathe, said she was introduced to the “idea of oral sex.” She said, however, she was nervous about their 17-year age gap and her sexual inexperience.

Eventually, during a boat trip to Miami, she had sex with the rapper for the first time, after Combs served her wine and the party drug, ecstasy. After that, she said, she thought they were in an exclusive relationship, but in hindsight she now knows that wasn’t true.

When asked why, she replied: “Sean Combs had many girlfriends.”

Ventura also noted that, early on in their relationship, they weren’t public about it. She said Combs had expressed concerns about perceptions, given that his company was also producing her music.

Soon, things began to take a dark turn, she testified. She said Combs became increasingly possessive and he would call her “incessantly” if she didn’t pick up his calls. He also sent staff members to track her down if he couldn’t reach her.

His moods were also intensifying around this time, Ventura said.

“Make the wrong face, and the next thing I knew, I was getting hit in the face.”

In the beginning, Ventura said, she was “insanely jealous.” She said that resulted from being “super young.”

“I didn’t get that he was him. As he would say, ‘I’m Puff Daddy. Puff Daddy has many rules. Likes the company of women,’” she recalled.

She said that as time passed, she came to believe “more often than not” that they were in a monogamous relationship. “He expected that of me so I assumed it was the same.”

She said Combs told her: “I’m not dealing with anyone else. It’s just us.”

She also told the court that Combs began paying the rent for apartments close to his own homes in Los Angeles and New York, where he would frequently show up, with his own set of keys, unannounced. She said his temper was mercurial and she never knew what to expect when he came over.

If she made Combs mad, she said, he would often take away her personal phone and laptop. While he would eventually return them, she said the length of time her electronics were confiscated “depended on how long I was being punished.”

Soon, Ventura said, she began participating in the “freak-offs,” which would last anywhere from 36 hours to four days, involved sex with “strangers” and “took a big chunk of my life.”

She said drugs were central to the parties and she would spend days recovering from the drugs, sleep deprivation and dehydration. She said she took the drugs — ranging from ecstasy, cocaine, marijuana, ketamine and magic mushrooms — for “dissociating,” and to have “some kind of buffer” from the experience.

“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,” she testified.

She told the court that sometimes the drugs made her feel like she was going to vomit. “If we were in the freak-off, he would be encouraging me to get up and continue on with it in that condition,” Ventura said of Combs.

After a brief lunch break, Ventura described to prosecutors the control Combs exerted over her appearance — he preferred that her nails be painted a certain colour and would make comments about the size of her breasts and her hairstyles.

She also said that she spent a lot of time getting ready for the freak-offs as she “had to look a certain way.”

Ventura said she attempted to let Combs know that these freak-offs — which over the course of their relationship increased in frequency and duration, happening weekly at this point — made her feel “horrible” and “worthless,” but he responded by being “pretty dismissive.”

Now choking back tears, she said the person she loved disappeared while the freak-offs were happening.

“His eyes go black — the version of him I was in love with was no longer there,” she said on the stand.

She said the freak-offs took place in various locales, including the Turks and Caicos Islands, New York City, Miami, Los Angeles and Las Vegas, among others, and usually happened in hotels. Combs was very particular about freak-off accessories, she said, and he was always certain to have the room stocked with baby oil, condoms and Astroglide, a lubricant. She said close to 10 large-sized bottles of baby oil would be used during one session.

She described the freak-offs as “very choreographed” by Combs.

Asked if there was anything she enjoyed about freak-offs, she responded, “The time spent with him.”

She explained that those encounters provided some of the only one-on-one time she had with Combs. The final one, she said, occurred in 2017 or 2018.

Ventura said the escorts were paid in cash, typically US$1,500 to $6,000. Sometimes Combs brought the money, she said, while sometimes it was up to a member of his security team.

In the aftermath of a freak-off, the room would be a mess, she said, baby oil all over the walls and the door handles. There would also be bodily fluids, with Ventura testifying that sometimes Combs ordered the sex workers to urinate on her.

“It was a turn-on for him, so it happened,” she said, describing a lack of consent or regard for her comfort or preferences.

“I was an object, being heavily objectified by men in that scenario,” she continued, describing her feelings in hindsight.

Combs didn’t always stay in the room to watch Ventura have sex with male sex workers, she said. Sometimes, he’d go to another room and watch them via FaceTime, the iPhone video call app, she testified.

Ventura also recalled an incident in which Combs left her during a freak-off at his Los Angeles home to confront rival record executive Suge Knight at Mel’s Drive-In, a landmark diner nearby.

Combs sprang into action after his bodyguard came in and told him of Knight’s whereabouts, she said. Combs and the bodyguard dressed in black clothes, grabbed guns from a safe and loaded into an SUV, she said. She testified that Combs gave her a gun to put in her purse — not the only time he made this request.

“I was crying. I was screaming, like ‘Please don’t do anything stupid,’” Ventura testified. “I was really nervous for them. I didn’t know what they were going to do.”

She said, “It’s like I wasn’t even there.”

Combs later returned, she said, but it was unclear what had happened, and he didn’t say anything.

Late in the day, Ventura shared the details of the day Combs assaulted her in the hotel hallway in March of 2016.

She said she was scheduled to attend her first big movie premiere in a couple of days and agreed to a freak-off as “damage control.”

“If I pleased him with a freak-off,” she told the court, “then my premiere would run smoothly.”

After watching the video of the hotel altercation from the stand, Ventura explained that she covered her face and stayed on the ground after Combs threw her to the floor because she “didn’t want him to do any more damage than he had already done.”

When asked how many times Combs threw her to the ground over the course of their relationship, she said there were “too many to count.”

Earlier in the morning, male stripper Daniel Phillip continued to be questioned by one of Combs’ lawyers, Xavier R. Donaldson. Phillip testified on Monday that he was hired by Combs and his then-girlfriend — Ventura — to have sex with her while Combs watched. Sometimes, he said, the rapper would direct what should happen.

Defence lawyer Xavier Donaldson pointed to Phillip’s past statements to federal prosecutors as he attempted to show inconsistencies in his recollection of events. Donaldson finished his cross-examination after suggesting Phillip had developed a crush on Cassie and wanted to isolate her from Combs so he could be with her romantically. Phillip denied that but admitted: “I was attracted to her. If she ever gave me the chance to date her, I absolutely would have.”

Once Donaldson was finished, a prosecutor asked Phillip more questions, underscoring the witness’ earlier testimony that it was Combs who directed his sexual activity with Ventura.

Combs is charged with sex trafficking, racketeering conspiracy and transportation to engage in prostitution. He has denied all the charges against him and rejected a last-minute plea deal earlier this month, choosing to go to trial instead.

If found guilty in the New York court, he could face life in prison.

Read more about Day 1 testimony and opening arguments.

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Global News will be covering the Diddy trial in its entirety. Please check back for updates. 

— With files from Global News’ Katie Scott and The Associated Press

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