How Cassie Ventura Responded To Lawyer's Claims That This Lawsuit 'Ruined' Diddy's Career
Day 3 of Diddy's trial is underway.

Sean Combs’ trial is underway after jury selection wrapped up Monday, and already we’ve learned why P. Diddy had a thousand bottles of baby oil in his homes, as well as heard testimony from Cassie Ventura about the infamous freak-offs. As the music mogul’s ex-girlfriend faced cross-examination on the third day of testimony, she responded to the defense’s claim that her 2023 lawsuit against Diddy ruined his career.
Cassie Ventura is viewed as a “pioneer” of sorts, as she's credited with kicking off the legal case against Diddy with her lawsuit in November 2023 that alleged rape, violence and trafficking during their relationship. While that suit was quickly settled, it seemingly inspired others to file their own complaints against Diddy. Defense attorney Anna Estevao asked Ventura on Thursday if it was “fair to say” her lawsuit had “ruined” her ex-boyfriend’s career, to which she replied (per Page Six):
I could understand that, yeah.
The defense argued that P. Diddy identifies with the swinger lifestyle after Cassie Ventura detailed the freak-offs, including how her then-boyfriend would bring a third party into the bedroom. Daniel Phillip also testified that he was paid on more than one occasion to have sex with Ventura while Diddy watched. In trying to paint her client as a swinger, not a criminal, the lawyer had this exchange with Cassie Ventura:
- Anna Estavao: Did you understand ‘Freak-Offs’ were consistent with Mr. Combs’ description of the swingers lifestyle?
- Cassie Ventura: Related in a sexual way … they’re very different.
This discussion about freak-offs and Sean Combs and Cassie Ventura’s bedroom activities came during what sounds like an intense day of cross-examination for Ventura. The witness, who chose to testify under her own name rather than anonymously, is 8 months pregnant with her third child with husband Alex Fine, and at one point, she reportedly asked for a break and was seen grabbing her belly with both hands.
The defense questioned why Cassie Ventura stayed in the 11-year relationship, and they read text messages sent during the couple's time together in which Ventura called herself a “lucky woman.” There were also more explicit texts in which she reportedly wrote she was “always ready to freak off” and detailed what she couldn’t “wait” for Diddy to do to her.
In addition to Cassie Ventura’s 2023 lawsuit against Diddy, another big piece of the case involves the leaked video that shows P. Diddy assaulting Ventura in a hotel. Because she was involved with the record executive for so long, she is seen as a star witness, and her testimony is a big part of the prosecution’s case.
Diddy has maintained his innocence amid the federal charges and civil accusations that have been made against him, and this case is just getting started. With plenty of testimony still to be heard, it’s expected that what Cassie Ventura has to say on the witness stand will have an impact on the jury’s decision regarding Diddy’s fate.
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Heidi Venable is a Content Producer for CinemaBlend, a mom of two and a hard-core '90s kid. She started freelancing for CinemaBlend in 2020 and officially came on board in 2021. Her job entails writing news stories and TV reactions from some of her favorite prime-time shows like Grey's Anatomy and The Bachelor. She graduated from Louisiana Tech University with a degree in Journalism and worked in the newspaper industry for almost two decades in multiple roles including Sports Editor, Page Designer and Online Editor. Unprovoked, will quote Friends in any situation. Thrives on New Orleans Saints football, The West Wing and taco trucks.
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