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NYTimes
New York Times
16 May 2025
Joe Coscarelli


NextImg:Takeaways From Cassie’s 3rd Day of Testimony in Sean ‘Diddy’ Combs Trial

In its cross-examination on Thursday of Casandra Ventura, the singer known as Cassie, Sean Combs’s defense team confronted her about dozens of messages between them, many explicit. His lawyers are hoping those communications will show that Ms. Ventura was a loving partner and an enthusiastic participant in the marathon sex sessions with prostitutes that Mr. Combs called “freak-offs.”

Ms. Ventura is expected to return to the stand for the final time on Friday. Here are four takeaways from her third day of testimony:

For the defense, confronting Ms. Ventura was a balancing act.

Given the beatings she had suffered at the hands of Mr. Combs and the fact that Ms. Ventura is nearly nine months pregnant, the tone of its cross-examination was an important consideration for the defense team. The judge alluded to Ms. Ventura’s pregnancy at one point while expressing frustration with the defense when it suggested its questioning of her might extend past this week.

Nonetheless, Anna Estevao, one of Mr. Combs’s lawyers, started out briskly. She skipped any extended pleasantries to the witness and jumped right into questions designed to suggest that Ms. Ventura had been a more willing, even enthusiastic, participant in the freak-offs than she had acknowledged in her direct testimony.

But Ms. Estevao’s confrontations never came close to the aggression that is often seen from defense lawyers cross-examining a star witness. She even shared a few laughs with Ms. Ventura, including one moment when she remarked how beautiful and charming the witness was. “Thank you,” Ms. Ventura replied.

It was not all so diplomatic, though. Ms. Estevao spent much of the day in painstaking readings of text and email messages that Ms. Ventura had shared with Mr. Combs. During one tedious recitation, the witness bluntly asked, “Do you have any questions for me?”

Explicit messages between the couple were a point of emphasis.

Much of Ms. Ventura’s testimony on Thursday morning was spent discussing messages — many of them explicit — that she and Mr. Combs had sent during their decade-long relationship.


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