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Casandra “Cassie” Ventura took the stand for her second day of testimony in Sean Combs’ criminal trial, during which she shared details of ex-boyfriend’s 2016 physical assault at the InterContinental hotel, which was captured on surveillance video; Combs’ reaction to her brief relationship with Kid Cudi; and a 2018 rape allegation.
The testimony follows Ventura’s first day on the stand Tuesday (May 13), during which she painted an extremely graphic picture of the “humiliating” sexual acts she said she endured to avoid Combs’ violence and sustain the hip-hop mogul’s love.
Early in the day, jurors once again were shown the surveillance footage of the 2016 assault before Ventura read aloud a series of text messages Combs sent her afterward. These included multiple requests to call him and claiming police were about to arrest him, as well as: “I got six kids,” “Yo pls call Im surrounded,” and “For my kids help.” Ventura texted Combs that she had spoken to security and “as long as you don’t disturb the guests they’ll leave you be.”
She went on to testify that Combs had given her a fat lip and a black eye as a result of the attack. “You are sick for thinking it’s okay to do what you’ve done please stay far away from me,” she texted him. She declined to give Combs’ name to the police, she said, because, ”I didn’t want to hurt him that way. [It was] just too much going on.”
Ventura — who is considered the star witness in the Southern District of New York prosecutors’ case — walked into court Wednesday wearing a gray turtleneck dress. It was the 38-year-old R&B singer’s November 2023 civil lawsuit against Combs that put a federal investigation into motion. Ventura revealed during her testimony that Combs settled the case for $20 million.
Ventura said she chose to come forward because she was tired of the “shame, the guilt” that stemmed from her relationship with Combs. “He brought the concept [of freak-offs] to me when I was 22, ” Ventura testified through tears. “I would do absolutely anything for him and I did. And it never stopped.”
In September, SDNY prosecutors charged Combs with the sex trafficking of two women between 2009 and 2024, racketeering conspiracy, and transportation to engage in prostitution. Combs, 55, has pleaded not guilty to the five felony charges against him. If convicted, he faces up to 15 years to life in prison.
Near the end of the day, Ventura alleged that Combs raped her in 2018. At the time, their relationship was ending, and Ventura had already begun seeing her now-husband, Alex Fine. She said she and Combs went to dinner in Malibu and had what she thought was a “closure conversation,” describing the mood as playful and romantic. But upon Combs driving her home and then “raped me in my living room,” she testified.
“I just remember crying and saying ‘no,’ but it was very fast,” she said. Ventura added that she wasn’t even sure Combs noticed her crying. (Per a previous ruling, Fine, who has otherwise been in attendance throughout Ventura’s time on the stand, was barred from hearing her testimony about the alleged rape because Combs’ defense said they may call him as a witness.)
Ventura went on to say she had sex with Combs one more time after their breakup, though this time “by choice.” Of that decision she noted their decade together and said, “You don’t just turn feelings off that way. I still had a good vision of who he was as a person.”
But the long-term effects of their relationship lingered, she said. Ventura broke down as she discussed her decision to enter rehab and a trauma therapy program in 2023. “I was spinning out,” she said. “I didn’t want to be alive anymore at that point.”
Ventura recalled having flashbacks during a music video shoot, and when she returned home, she told Fine, “You can do this without me. You don’t need me anymore.” She added, “I couldn’t take the pain that I was in anymore, and so I just tried to walk out the front door into traffic and my husband would not let me.”
Around this time, Ventura said she entered rehab where she first began “putting everything on paper for the first time so that I could really understand what I had been through over many years.” She described her treatment for coming off Valium as being more of a “trauma therapy.”
Afterwards, Ventura said she took all of her writing and fashioned it into a book, wanting Combs to read it. “I just wanted him to understand,” she said. “I don’t think, after all those years of begging for, like, sorries, and just for him to actually recognize the pain, the pain that he put me through.”
Ventura said she also wanted compensation from Combs “for the time, the pain, and like the many, many years of trying to have to fix my life.” Ventura said she randomly landed on $30 million, choosing a number that would “alert” him. But Combs never paid for the rights to the book. Instead, Ventura said he ended up paying a $20 million settlement to her when she filed her sex trafficking lawsuit.
Throughout her testimony Wednesday, Ventura shared many alleged instances of physical violence, including during “freak-offs” — the lengthy, drug-fueled sexual encounters Combs allegedly orchestrated with Ventura and male sex workers. Ventura said she was injured during freak-offs, sometimes with an escort still in the room, when Combs “put hands on [her].” She added that these alleged incidents happened “too frequently.”
Ventura also detailed a 2013 incident where she said Combs came to her apartment and started berating her for sleeping when she should have been packing for an upcoming trip. Ventura said two of her friends, who were there at the time, jumped on Combs’ back “because he was trying to attack me.”
At one point during the scuffle, Ventura said Combs threw her down. “I hurt my eyebrow on the corner of my bed,” she said, adding that she was left with a “pretty significant gash on the side of my eyebrow.”
Later that day, Ventura said, one of Combs’ security guards took her to a plastic surgeon to suture the wound. She said she took a photo and texted Combs, “So you can remember.” On the witness stand, Ventura pointed to her eyebrow and said she still has a scar from the incident, which she covers with makeup. Prosecutors showed the jury a photo of Ventura with the eyebrow injury.
During her second day of testimony, prosecutors again questioned Ventura at length about the freak-offs, focusing on the physical toll they took. Ventura read text messages she sent Combs about sores on her tongue, which she attributed to performing oral sex and taking drugs. She also said she frequently suffered from urinary tract infections, yet would continue to perform during the freak-offs despite “horrible” pain.
After the freak-offs, Ventura continued, she and Combs would recover with massages and IV fluids, but also opiates, which Combs allegedly provided at times. Ventura said she developed an “off-and-on” opiate addiction, adding, “Opiates made me feel numb, which is why I relied on them so heavily… I didn’t want to feel what was actually going on in my mind, in my life, in real time. It was just an escape for me.”
Ventura also testified about the videos Combs allegedly made of the freak-offs, which she said were turned into “blackmail materials.” She said Combs frequently brought up the videos when he was angry with her, and threatened to release them as a way to keep her in-line.
One such instance, Ventura said, was when she started dating Kid Cudi (real name Scott Mescudi) in 2011. She testified, per reports, that Combs threatened to release freak-off videos after learning about their relationship. And she claimed that Combs threatened to “hurt” her and Mescudi, with Combs allegedly saying he would be out of the country when it happened.
Ventura also claimed that Combs discussed blowing up Mescudi’s car, and claimed Combs said he wanted Mescudi’s friends to see the explosion. In 2012, a Porsche owned by Mescudi was set on fire by an “incendiary device,” as a contemporaneous police report put it.
Ventura testified that, after she ended her relationship with Mescudi, she next saw him at SoHo House, with Combs also present. Ventura testified that Mescudi asked Combs, “What about my vehicle?” To which Combs allegedly replied, “What vehicle?” Ventura said “that was the end of the meeting.”
Another alleged incident occurred during a trip to the Cannes Film Festival, where Ventura said Combs accused her of stealing drugs from him, then kicked her off of his boat. On the flight back home, Ventura said, she tried to avoid Combs, but he eventually traded for a seat next to her, and started playing videos of freak-offs that Ventura thought she had deleted. She said Combs told her “he was going to embarrass me and release them.”
Ventura said she “felt trapped,” and when they landed, Combs wanted to have a freak-off. “At that point, whatever was going to make him not be angry at me and threatening me, I was willing to do,” she said. “I just didn’t want to feel scared anymore. It was the one thing he made me feel like I was good at.”
She testified that at one point, she texted Combs that “nothing good” came out of the freak-offs. “You treat me like you’re Ike Turner,” she texted.
Much of Ventura’s testimony during her first day on the stand centered on how she came to find herself unable to say “no” to Combs. He became her label boss in 2006 when she signed with Bad Boy, and shortly after her 21st birthday in August 2007, Combs began to pursue her romantically.
She said these overtures were “confusing” at first, but Ventura said she quickly became “enamored” of Combs, and by later that year — after a fake work trip to Miami where the pair first had sex and Ventura first knowingly took the party drug Molly — Ventura said they were in a relationship.
Within the first year of dating, Ventura claimed Combs “proposed to me this idea, this sexual encounter that he called voyeurism, where he would watch me be — have intercourse and sexual activity with a third party, specifically another man.”
She would come to know these sexual encounters as freak-offs and said over the course of their decade-long relationship, Combs demanded freak-offs almost weekly. “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 testified.
Ventura briefly testified about the physical abuse she claimed began early on in their relationship and happened “too frequently.” “He would mash me in my head, knock me over, drag me, kick me, um, stomp me in the head, if I was down,” she said.
She also spoke about the alleged control Combs had over her life, including her living arrangements, her appearance, and her music career. Ventura also said Combs filled her day with “busy work” when she was not with him.
However, much of the day was focused on the “humiliating” and “disgusting” sexual acts that Combs allegedly directed her and male escorts to perform during the freak-offs. Ventura claimed that Combs “controlled” the highly choreographed sexual encounters, approving the male escorts (that Ventura said she was tasked with hiring), as well as the outfits she wore.
Ventura said she felt she couldn’t say “no” to Combs, fearing that something “bad” would happen. “His temper,” Ventura explained. “If that is something that he wanted, Sean wanted to happen, that’s what was going to happen. There wasn’t another way around it.”
She also expressed anxiety that if she refused Combs, the perpetual bachelor would discard her, finding another woman to have freak-offs with. She testified that her self-worth plummeted over the course of their relationship.
This story was updated at Wednesday, May 14 at 8:35 p.m. to include details about Sean Combs’ November 2023 civil settlement with Casandra Ventura, and why she decided to come forward.
From Rolling Stone US.