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.
“I can’t wait to stare,” Ms. Ventura wrote, adding a description of genitalia, in one 2009 conversation that was shared in court.
“I can’t wait to watch you,” Mr. Combs responded. “I want you to get real hott.”
“Me too,” she replied. “I just want it to be uncontrollable.”
The defense appeared to be emphasizing the love and passion in the early stages of their relationship, citing flirtatious messages and those in which she seemed to express eagerness for freak-offs, offering to pick up supplies at a sex shop. “I’m always ready to freak off lolol,” Ms. Ventura wrote at one point.
The messages also showed that, at certain times, Ms. Ventura expressed dissatisfaction with their arrangement. She testified that she had been jealous of Kim Porter, Mr. Combs’s longtime partner, and other women that he would start relationships with.
“I get nervous that i’m just becoming the girlfriend that you get your fantasies off with and that’s it,” she wrote.
How jurors view Ms. Ventura’s credibility will be crucial.
Mr. Combs is charged with sex-trafficking Ms. Ventura, a crime that would require the government to prove that he forced or coerced her into sex parties with male prostitutes.
Over her first two days on the stand, Ms. Ventura testified to years of physical violence and sexual coercion by Mr. Combs so severe that she considered suicide. In Thursday’s cross-examination, a defense lawyer focused on a different side of their relationship.
Ms. Estevao asked Ms. Ventura about dozens of pages of text and email messages between the couple. The cross-examination also highlighted Ms. Ventura’s complex relationship with freak-offs: Outwardly, she sometimes expressed enthusiasm about the encounters to Mr. Combs, but inwardly, she testified, she had a deep aversion to them.
It remains to be seen how the jury will ultimately view Ms. Ventura’s testimony.
The defense sought to connect Mr. Combs’s behavior to his drug use.
Much of the questioning from Mr. Combs’s defense team focused on drug use and abuse, and its potential influence on the behavior of both Mr. Combs and Ms. Ventura.
Ms. Ventura said both she and Mr. Combs were dependent on opiates for most of their relationship, and that he did other drugs, including Ecstasy, cocaine, ketamine and GHB, in her presence.
She testified that Mr. Combs overdosed on opiates in 2012, after they had gone to a sex club in the Los Angeles area and he then attended a party at the Playboy Mansion. She also said that both of them had tried to detox by using Ibogaine, a natural psychedelic, which they had obtained in Mexico; the treatment temporarily worked before relapses.
Several times, Ms. Estevao asked questions about the symptoms of drug withdrawal, in a seeming attempt to connect Mr. Combs’s behavior and mood with his drug use and recovery.
On Tuesday, Ms. Ventura had testified that she used drugs at freak-offs — Ecstasy, cocaine, marijuana, ketamine, mushrooms — to dissociate from the events. But under cross-examination, she also spoke about her drug use outside of these planned sexual encounters. Using drugs with people other than Mr. Combs made him jealous, she said.
She testified that an incident she described in her direct testimony — when Mr. Combs was angry at her during a trip to Cannes — was the result of him suspecting she had taken drugs from him without asking. A physical altercation with one of Ms. Ventura’s former friends was the result of Mr. Combs seeing drugs on a table that they had planned to take together.
As testimony was wrapping for the day, Ms. Estevao questioned Ms. Ventura about the drugs she and Mr. Combs consumed at the freak-off related to the 2016 encounter where Mr. Combs was seen on surveillance footage assaulting her in a hotel hallway.
“Do you recall the beginning of the freak-off session?” Ms. Estevao asked. Ms. Ventura said she did not, but guessed that she had taken MDMA or Ecstasy. Asked if it was a bad batch of drugs, Ms. Ventura said she had no idea.
Ben Sisario, a reporter covering music and the music industry, has been writing for The Times for more than 20 years.
Julia Jacobs is an arts and culture reporter who often covers legal issues for The Times.
Joe Coscarelli is a culture reporter for The Times who focuses on popular music and a co-host of the Times podcast “Popcast (Deluxe).”
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