It was only about a half-hour into the cross-examination of Casandra Ventura that a lawyer for Sean Combs drew on messages the couple exchanged, in an attempt to establish one of the defense’s key arguments in the case: that Ms. Ventura was a willing participant in the sex marathons known as “freak-offs.”
Anna Estevao, the defense lawyer questioning Ms. Ventura on Thursday, presented a message the singer wrote to Mr. Combs in 2009, that read, “I’m always ready to freak off lolol.”
In another exchange from around that time, Ms. Ventura expressed her excitement in graphic terms, and he told her: “I can’t wait to watch you. I want you to get real hott.”
She answered: “Me too. I just want it to be uncontrollable.”
Conversations like those, which could involve both explicit flirtation and logistical planning about their meetings and preparations, were “somewhat typical” for the two, Ms. Ventura testified.
Those messages showed a very different side of the relationship than what Ms. Ventura described in the first two days of her testimony, under questioning by prosecutors. Over hours of sometimes excruciating testimony, she said that Mr. Combs had forced her to take part in “hundreds” of these episodes over about 10 years, and used violence and threats of releasing explicit videos from the freak-offs as what she called “blackmail materials.”
Mr. Combs, who is charged with sex trafficking and racketeering conspiracy, has pleaded not guilty, and his lawyers have vehemently denied that any of his sexual encounters were not consensual.
The cross-examination highlighted Ms. Ventura’s complex relationship with freak-offs over the yearslong relationship: Outwardly, she expressed enthusiasm at times about the encounters to Mr. Combs, but inwardly, she testified, she had a deep aversion to them.
In her testimony, Ms. Ventura has said that she did not want to participate in freak-offs, despite evidence from text messages and other communications at the time in which she seemed to express not only willingness but excitement. Part of her reasoning, she said, was out of her love and devotion to Mr. Combs at the time. Eventually, she testified, she tied her willingness to engage in the freak-offs to her fear of violence and threats from Mr. Combs. She testified that at times, she expressed discomfort with the arrangement, and Mr. Combs was “pretty dismissive.”
Beyond its attempt to establish consent, the defense tried to make the argument that Ms. Ventura’s hesitancy about these encounters as their relationship developed stemmed mostly from her fear of being relegated to the role of freak-off partner rather than Combs’s true girlfriend.
“I get nervous that I’m just becoming the girlfriend that you get your fantasies off with and that’s it,” she wrote to Mr. Combs in an email in 2009.
Sitting between his lawyers in the courtroom on Thursday, Mr. Combs, who wore a sand-colored sweater and collared shirt, was more fidgety than he had been earlier in the week, leaning back and forth in his chair and taking his black-framed glasses on and off. During a break, Mr. Combs handed a note to Ms. Estevao, as he has sometimes done to his legal team during the proceedings this week. Mr. Combs’s three sons and his mother, Janice Combs, sat in the spectators’ gallery.
Ms. Ventura, who is visibly pregnant, wore a double-breasted black suit jacket over a light colored shirt, her long dark hair pulled back. She began testifying a little after 9:30 Thursday morning and continued for about three hours, with some short breaks.
In the first hours of her cross-examination, Ms. Estevao also recalled parts of Ms. Ventura’s testimony from earlier in the week, when the singer said she had agreed to take part in freak-offs because she loved Mr. Combs and wanted to make him happy.
Ms. Estevao, whose tone was largely measured and conversational, though she seemed to stumble at points during her questioning, began the day by asking about tender and flirtatious messages Ms. Ventura and Mr. Combs had written each other in the early stages of their relationship.
“I’m a very lucky woman,” Ms. Ventura wrote in 2008.
A couple years later, Mr. Combs messaged her: “I love you so much it consumes my life.”
Ms. Estevao asked her: “You knew the Sean that he didn’t want anybody else to see but you?” Ms. Ventura did not disagree with her.
But Ms. Ventura showed some resistance when Ms. Estevao questioned her motivation for participating in the sex marathons. In one exchange, the lawyer asked, “So, to make him happy you told him that you wanted to do freak-offs, right?”
“No,” Ms. Ventura replied. “There’s a lot more to that.”
On the stand, Ms. Ventura was calm and soft-spoken, but sometimes offered salty responses to Ms. Estevao’s questions. At one point, while Ms. Estevao read from a series of text messages, Ms. Ventura asked, “Do you have any questions for me?”
Whether Ms. Ventura, and other woman involved in the case, participated in the freak-offs willingly is a crucial point of dispute in the trial.
During the defense’s opening statement on Monday, Teny Geragos, one of Mr. Combs’s lawyers, described the women at the center of the government’s case as “capable” and “strong.”
“For Cassie, she made a choice every single day for years. A choice to stay with him — a choice to fight for him,” she said. “Because for 11 years, that was the better choice. That was her preferred choice.”
Olivia Bensimon contributed reporting from the courtroom.
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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