Cassie faces skeptical cross-examination from Diddy’s defense team

May 15, 2025
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Casandra Ventura, the R&B singer and model who has accused Diddy of physical and sexual abuse, faced cross-examination today from Anna Estevao, one of the rapper’s lawyers. Estevao set out to portray Ventura as a willing participant in Diddy’s “freak offs,” challenging the singer’s insistence that she was coerced into the drug-fueled, voyeuristic sexual encounters.

  • Ventura, who is visibly pregnant, acknowledged that the early years of her off-and-on relationship with Diddy were “loving,” though sometimes riven by jealousy. She remembered him as a “charismatic” and “larger-than-life” personality who could be “sweet” and “attentive.”
  • Estevao showed jurors text messages the defense team believes rebut Ventura’s claims. “I’m always ready to freak off,” Ventura wrote in 2009. “I can’t wait,” she wrote before one such event that same year. Ventura testified yesterday that she never wanted to participate in the marathon sex sessions but felt she needed to keep Diddy happy.
  • Diddy and Ventura argued about infidelity, and “it was a little scary” when he accused her of cheating, she told jurors. Ventura said she had “some jealousy” toward the late Kim Porter, one of Diddy’s ex-partners and the mother of three of his kids; Diddy was “irate” about Ventura’s brief relationship with rapper Kid Cudi, she said.
  • Estevao attempted to connect Diddy’s drug use to his alleged pattern of violent behavior. Ventura said the hip-hop mogul was once addicted to opiates and overdosed in 2012. The painkillers he took were “a part” of his mood swings, she said. Ventura testified that she was dependent on drugs during the relationship, too. 

The view from inside

By Adam Reiss and Doha Madani

When cross-examination started, Ventura spoke with trepidation and caution. But she seemed to gain confidence as the day went on, answering questions calmly and politely. She occasionally expressed confusion about certain queries. Estevao initially appeared to struggle to find a rhythm, repeatedly starting and stopping, but she settled into a steady groove after lunch. 

Diddy’s three sons as well as his mother, Janice Combs, sat in the gallery today. The rapper’s mom has been in the federal courtroom in downtown Manhattan every day this week, listening to extraordinarily graphic testimony about her son’s alleged history of violent abuse and sexual proclivities.

Judge Arun Subramanian looks determined to keep the trial moving at a brisk clip. He promised jurors they would be done with their service before July 4 — and he appears mindful of the fact that Ventura is potentially days away from giving birth. He sternly reminded the defense it was given a day and a half to question her, and scolded Diddy’s lead attorney after he pushed back.

“In what universe did you not understand that this was important,” Subramanian asked the attorney, Marc Agnifilo.

In other news: The prosecutors and defense lawyers seemed to have a cordial rapport during pretrial hearings. But it has quickly evaporated this week. The tension in the courtroom ramps up dramatically whenever the jury isn’t seated. This morning, for example, the lawyers on opposing sides got into a heated dispute over which text messages the defense can introduce as evidence.

Diddy, meanwhile, took notes on a pad while those arguments unfolded.


Analysis: Consent or coercion?

By Danny Cevallos

Ventura’s testimony on cross-examination will read well for the prosecution on the transcript. It might not have sounded as good to the jury. That’s because a transcript doesn’t capture the cadence, inflection and mood of the answers. For jurors, who are listening to her testimony live and watching her body language, Ventura’s testimony could go either way. 

On the one hand, she is answering the questions — and she is mostly saying what the prosecution needs for its case. But on the other hand, some questions have no good answers. When the defense confronts her with text messages that suggest she was a willing participant in the “freak off” lifestyle, there really is no perfect response for Ventura.

It’s entirely possible jurors will see her as a victim who was unable to extricate herself from Diddy’s clutches. They may see her as someone coerced into the lifestyle. But it’s also possible that one or more jurors might conclude that Ventura repeatedly chose to be with Diddy and join in “freak offs,” sometimes with enthusiastic messages to him. It takes only one juror to deadlock.


What’s next

Tomorrow: Ventura will return to the witness stand for more cross-examination by Diddy’s team. The judge and prosecutors have made clear they’d like questioning to wrap by the end of the day.



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