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On the third day of her testimony at Sean “Diddy” Combs’ high-profile federal trial, Casandra “Cassie” Ventura was cross-examined by the defendant’s attorney, Anna M. Estevao.
During the May 15, 2025, cross-examination, past text exchanges between Cassie and Diddy were read aloud in the courtroom. While Estevao read Combs’ messages, Ventura read out her own.
Diddy, in an August 2009 text, seemingly wrote: “When do you want to freak off? Lol.”
Cassie seemingly replied, “I’m always ready to freak off LOLOL.”
Combs texted back, "You tell me the day. You choose. Name the day."
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The text exchange has now gone viral on the internet. According to Business Insider reports, they were displayed on the screen inside the Manhattan federal courtroom for the four women and eight men jury to look at.
More about Cassie’s text exchange with Diddy as revealed in the latter’s trial
Casandra Ventura delivered a lengthy testimony with the help of the prosecution in the ongoing sex trafficking trial of her former boyfriend, Sean Combs, on May 13 and 14.
However, on Thursday, the defense attorney Anna Estevao cross-examined her. During the proceedings, Cassie and Diddy’s explicit text exchange from 2009, when they were in a relationship, was read aloud in the courtroom.
In continuation of the above-mentioned messages, Combs replied to Ventura:
"I can't wait to watch you. I want you to get real hott."
The Me & U singer further responded:
"Me too. I just want it to be uncontrollable."
On another occasion, Cassie seemingly wrote to Diddy how she would set up a room for a planned freak off session.
"I'm going to Duane Reade to grab candles and then going home to pack us a bag," the text read.
A message from December 2009 showed the R&B singer confronting the rapper when she thought he wasn’t paying attention to her.
"When we used to freak off, we were so in love. I'm nervous that I'm just becoming the girlfriend that you get your fantasy off with, and that's it… I don't get the other part… Anymore at least," the text read.
In a follow-up message, Cassie also confronted her former boyfriend for not giving her attention while traveling. The 2010 text read:
"I know you can take 3 minutes out of your day to talk to me, and you don't even try. You're in too much of a rush to get me off the phone."
Meanwhile, text chains from the end of their relationship were also read out in the courtroom.
One 2017 message revealed Cassie telling the Love Album maker that she was seemingly “excited” about one of their upcoming freak-offs, adding she forgot her iPad, which she previously testified was used to record their sessions.
Another text from May 2017 showed Casandra informing Combs that she was on her way to a sex shop called Pleasure Chest to get freak-off supplies, and the latter texted back, asking her to “have fun, impress me.”
Other text exchanges revealed Ventura telling Combs she was “grateful” to be in his life, but worried that he was “constantly weary” of her. This came right after her 21st birthday.
Another DM showed the former couple discussing how to avoid getting pregnant after “one of our nights.” At this point, the witness asked for a short break, which the judge granted her, while the jury was also sent on a brief recess.
Earlier during her two-day-long testimony, Casandra Ventura, 38, testified that she loved Sean Combs, 55, but hated the freak offs, adding she often joined them unwillingly, even though she felt “worthless.”
She went on to add that she wanted to make Diddy “happy” and the freak-offs were the “only time” she got to spend with him.
"I felt pretty horrible about myself. I felt disgusting. I was humiliated. I didn't have the words at the time to tell him how I felt. And I couldn't talk to anyone about it," Cassie stated.
She also mentioned Combs reportedly coerced her into the freak-offs, and she participated in them to seemingly avoid his anger and alleged physical abuse.
Elsewhere, the dancer-model name-dropped several former associates of Diddy who seemingly helped him organize the freak-offs, while also testifying about the alleged domestic abuse.
Cassie's testimony also contained her anecdotes about the alleged sexual, physical, emotional, and psychological assault that she reportedly faced during her 11-year-long relationship with Diddy, between 2007 and 2018.
Freak-offs organized by Combs, refer to drug-fueled and days-long sex-based performances that are at the heart of his federal trial, where he is fighting multiple criminal charges, including sex trafficking by force, fraud, or coercion, racketeering conspiracy, and transportation to engage in prostitution.
Cassie, who is eight months pregnant, arrived in the court with her husband, Alex Fine. The pair already has two kids with a third one on the way.
On Thursday, defense attorney Anna Esteveo repeatedly asked Venture to raise her voice while reading aloud the text exchange.
Meanwhile, Ventura addressed the jury and shared the full context of her text exchanges with Combs were not being revealed and there was a lot they "skipped over."
Elsewhere, Esteveo told Judge Arun Subramanian that she expected to finish cross-examining by Friday and prove that Cassie and other plaintiffs/ accusers participated in the freak-offs both consensually and voluntarily.
