Cassie Ventura spent the early part of the week testifying before a federal jury about her nearly 11-year relationship with Sean ‘Diddy’ Combs, as part of his sex trafficking and racketeering trial. His lawyers spent the next two days in cross-examination trying to dismantle her account.
Every narrative Cassie shared of herself and her time with the mogul, Diddy, was challenged by his attorney Anna Estevao, on Thursday and Friday—often using the singer’s own words from texts and emails.
Defense challenges Cassie’s testimony
Even more than the revelations about drug dealers and eight-figure settlements, this set of attempted reversals was the central story of the cross examination of the government’s star witness. If Cassie painted one picture of an aspect of her life between 2009 and this month, Estevao worked overtime to give the jurors on the case an alternative that favored her client.
The most important example of this centered around freak offs, the sometimes days-long, highly choreographed, drug-fueled sexual encounters involving Combs, Ventura, and escorts.
A large part of the government’s case centers on the idea that the freak offs were a result of, as the charging document in the case puts it, “force, fraud, or coercion.” This is consistent with what Cassie said during her direct testimony: that she didn’t want to take part in the freak offs, but that a combination of Diddy’s violence, his financial control over her, and his manipulation of her love for him made her do it.
Estevao made sure to spend a great deal of time over the two days of her cross making Cassie read her own texts, sometime graphic ones, about freak offs. Taken solely at face value, the texts portrayed a woman who was willing to take part in, and sometimes even initiated, the encounters.
Over and over again, the attorney would show Cassie sending messages like, “I’m always ready to freak off lolol” or “Wish we could have fo’d before you left” or suggesting things like a “freak off with a girl.”
In fact, the defense’s cross examination ended on a moment like this: sharing a text exchange from 2012 where Diddy asked, “Wanna freak off one last time tonight?” and Cassie answered: “I don’t want to freak off for a last time. I want it to be the first time for the rest of our lives.”
How Diddy maintained control
Because witnesses are restricted to answering only questions they are directly asked while testifying, Cassie was unable to contextualize her messages. This began to visibly wear on her after a number of hours.
At one point, after going back and forth with Estevao about one of these exchanges, she said in what appeared to be frustration, “This isn’t about what I feel is relevant, right? There’s a lot that we skipped over.”
Attempting to move Cassie from unwilling to willing freak off participant was far from Estevao’s only gambit. In her direct testimony, Cassie had portrayed herself as naive and inexperienced when she and Combs started dating not long after her 21st birthday. Estevao took time to point out that before dating Combs (17 years her senior), the singer had been in a three-year relationship with the musician Ryan Leslie, who is 10 years older than her.
Cassie said that Combs’ years of berating took a severe toll on her self-worth. To counter that, Estevao said to her, “You’ve always been self-conscious about your musical talents.” The attorney implied that Cassie being in the recording studio with talents like Lil Wayne, Nicki Minaj, and Rick Ross, and needing to have her own work meet their high standards, had as much to do with her feelings of self-doubt as anything her client may have done.
Cassie spoke of Combs’ financial domination over her life: that he paid for her housing and other expenses as a means of maintaining control. Estevao painted a picture of a young woman who, prior to dating Combs, had already saved up money from a successful modeling career, had a powerful manager in the late Ed Woods, and was already hanging out with celebrities like Britney Spears and Dallas Austin, both of whom attended her 21st birthday party in Las Vegas.
Cassie’s allegations of sexual assault and blackmail under Scrutiny
One of Cassie’s arguments was that Diddy frequently used videos of freak offs as blackmail, to keep her in line and compliant for fear of, among other things, ruining her career if the videos were released. Estevao said that Cassie’s November 2023 civil suit against Combs did in fact ruin his career, in what some observers took to be an intended parallel.
Combs’ domestic violence, which his team admitted to in their opening arguments, was portrayed by the government as a part of his larger criminal enterprise: it was a conscious way of keeping Cassie in line so he could continue with his freak offs. To Estevao, on the other hand, the beatings often came during drug-fueled “black outs” that he wouldn’t remember afterwards. Or, alternately, they happened because he was irritable as a result of withdrawal from opioids, which his team presented him as addicted to (this narrative seems to be the reason that his 2012 overdose on painkillers finally became public). Or, in the case of the now-infamous abuse at the Intercontinental Hotel, the violence came as the result of what Estevao called a “bad batch” of MDMA or Ecstasy.
Cassie spoke about a time that she said Combs raped her in August, 2018. Estevao attempted to turn that around as well, pointing out that in her civil suit, the singer had originally placed the event as occurring in September.
Ventura also said during direct that she had sex with Combs consensually the month after the alleged rape. During cross, Estevao elicited the detail that during that meeting, Cassie received (but did not answer) a Facetime call from Alex Fine, her now-husband, who she was dating at the time.
While Estevao did not say this outright, it appeared at least to some observers that she was trying to imply that the rape and the consensual sex with Combs were in fact the same event—that Cassie had described a consensual encounter as rape in order to disguise it from Fine. Ventura, however, was clear in saying in both direct and cross that the alleged rape and her consensual sex with Diddy were two separate events.
An emotional ending to week one of the Diddy trial
On Friday afternoon, prosecutor Emily Johnson got a chance to question Ventura once Estevao was finished, in a process called redirect examination. The singer said at that point that she had wanted to have sex solely with Combs during the entirety of their relationship, and did not want to participate in freak offs “at all.” She felt, she explained, that she could not say no.
“I was worried for my safety,” she said. “I was worried for my career. But I was in love with him, so I was worried that he wouldn’t want to be with me anymore [if I stopped participating in freak offs].”
In a dramatic moment during the end of her questioning by Johnson, Ventura broke down in tears when describing how she felt when Combs abused her during freak offs.
“Worthless. Like dirt,” she said. “That I was nothing. Absolutely nothing.”