Lawyers for Sean Combs worked on Thursday in court to portray his former girlfriend, Casandra Ventura, as a willing and full participant in sex marathons with prostitutes, as they sought to undermine her harrowing account of an abusive, coercive relationship riddled with violence.
Ms. Ventura’s credibility is central to the government’s case, in which they have charged Mr. Combs, the music mogul, with sex trafficking and racketeering. Earlier this week she told the jury of eight men and four women of how she had suffered through hundreds of degrading sexual encounters and many injuries out of a misguided attempt to please a man she loved.
But on the fourth day of Mr. Combs’s trial, the defense tried to recast Ms. Ventura, a singer known professionally as Cassie, as not nearly the victim she had portrayed herself to be. During cross-examination, Anna Estevao, one of Mr. Combs’s lawyers on a team led by Marc Agnifilo, repeatedly had her read text messages in which she expressed graphic enthusiasm for their sexual encounters, including the now famed “freak-offs” involving paid escorts.
“I’m always ready to freak off lolol,” Ms. Ventura said in a message from 2009.
In another exchange from around the same time, Ms. Ventura expressed her excitement in graphically sexual 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.”
Jurors gazed at the barrage of text messages, which were displayed on screens in front of them, sometimes leaning forward to get a closer look.
Mr. Combs has pleaded not guilty to the charges and his defense has argued that the government is trying to criminalize unconventional, but lawful, sexual relations between consenting adults. In her first two days on the stand, Ms. Ventura said that she might have feigned interest at times to avoid Mr. Combs’s anger, and she recited a litany of incidents in which she was beaten when she failed.
The defense, though, presented a series of emails and text messages in which Ms. Ventura was explicit in her description of sex acts she envisioned and engaged in the logistical planning for the freak-offs. The singer agreed with a defense assertion that the drugs they consumed provided a measure of intimacy, one she cherished in their peripatetic lives.
Though the defense displayed texts where Ms. Ventura appeared excited to meet Mr. Combs at hotels for the sessions, she noted at one point that the messages where she presented as enthusiastic were also “just words.”
Nonetheless, they showed a different side of the relationship than what came through in Ms. Ventura’s first two days of sometimes excruciating testimony. In those moments, she recounted multiple beatings that began early in their relationship, portrayed Mr. Combs as a control freak and said that, if she displeased him, he threatened to blackmail her by releasing explicit videos from the sex marathons.,
The defense on Thursday pushed back on much of that.
What Ms. Ventura had presented as Mr. Combs’s controlling obsession with what she wore and her appearance, the defense team suggested was an outgrowth of Mr. Combs’s expertise as something of a fashion maven. Wasn’t he was known for setting trends and for owning a clothing line, Ms. Ventura was asked? Yes, she responded, adding that Mr. Combs had a “big impact” on fashion and that people liked “his style.”
The defense also worked to defuse Ms. Ventura’s testimony that Mr. Combs supplied drugs for the freak-offs, including one that allowed her to ” disassociate” from sex that she wanted no part of.
Under cross-examination on Thursday, she acknowledged having her own appetite for drugs, that she and Mr. Combs saw themselves as “high partners” and that late in their relationship he became an active force against her using drugs, going so far as to warn street dealers not to sell to her.
Ms. Ventura also agreed with an assertion by the defense that the couple were addicted to painkillers for almost the entire duration of their relationship, delving at one point into describing that Mr. Combs had quietly suffered an overdose in 2012.
In fact, in one part of the cross-examination, the defense presented through its questioning the sense that Mr. Combs was not violent toward Ms. Ventura because he sought to force her participation in freak-offs, but rather was an addict who erupted when drugs sunk him into foul moods.
In addition to racketeering conspiracy and sex trafficking, Mr. Combs, 55, one of the most successful producers and entrepreneurs in the history of hip-hop, is charged with transportation to engage in prostitution. If convicted on the most serious charge, he could spend the rest of his life in prison.
Defense lawyers have admitted to what they described as Mr. Combs’s flaws, his bad temper and jealousy. They acknowledge domestic abuse. But they appeared on Thursday to be suggesting to the jury that the inflicting violence on Ms. Ventura was not the behavior of a racketeering kingpin wielding beatings like a tool, but of an addict whose mood swings and jealousy led to the angry outbursts.
The trial is taking place in a packed courtroom on the 26th floor of a Southern District of New York courthouse. Sitting between his lawyers, Mr. Combs wore a sand-colored sweater and a collared shirt and appeared more fidgety than on previous days. He leaned back and forth, taking his black-framed glasses on and off. His three grown sons and mother, Janice Combs, sat in the spectators’ gallery.
Ms. Ventura, who is eight-and-a-half months pregnant, is now married to Alex Fine, who was once both her own and Mr. Combs’s personal trainer. She clutched what appeared to be a chain of beads with a tassel as the jurors filed in. Once on the stand, she seemed weary of the defense’s many recitations of text messages and emails that presented various views into her relationship with Mr. Combs.
“Is there a question coming?” she asked Ms. Estevao at one point, looking mildly annoyed.
The defense set the tone for Thursday’s questioning with their first pieces of evidence, loving messages between the pair at the beginning of their relationship.
“I miss you sooo much and I’d fly wherever you needed me whenever!!!!!!!” Mr. Ventura wrote in 2008.
In 2009, Mr. Combs messaged her: “I love you sooooo much it makes me cry.”
When Ms. Estevao asked Ms. Ventura why she fell in love with Mr. Combs, the singer described the beginning of their relationship — when she was 19 and he was in his mid-30s — as fast-paced and “scary.” But she testified that “his real personality — or at least what I thought was his real personality — came out and I liked who he was.” She called Mr. Combs “sweet” and “attentive.”
The defense characterized Mr. Combs’s sexual preferences as part of a “swingers” lifestyle — in contrast to the government’s allegations of sex trafficking and coercion. When Ms. Estevao asked Ms. Ventura about swinging as a lifestyle, Ms. Ventura testified that several times she watched Mr. Combs having sex with another woman, a reversal of the typical voyeuristic arrangement that played out during their relationship where Mr. Combs watched Ms. Ventura having sex with male prostitutes.
Whether Ms. Ventura, and another woman involved in the case, participated in these sessions willingly is a crucial point of dispute in the trial.
On Monday, during the defense’s opening statement, Teny Geragos, one of Mr. Combs’s lawyers, described Ms. Ventura and the other 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,” Ms. Geragos said. “Because for 11 years, that was the better choice. That was her preferred choice.”
In the face of Ms. Ventura’s compelling account of suffering for love, the defense has tried to suggest that, for her, money, bitterness and the need to settle scores became equally motivating.
On Thursday, during a very brief but charged back-and-forth between Ms. Ventura and Mr. Combs’s defense team, the singer was asked about the effect of the lawsuit she filed in 2023 that accused him of much of the conduct for which he is now being tried. Mr. Combs quickly settled the suit after one day, and agreed to pay her $20 million.
“When your lawsuit was publicized in November 2023, you understood that his career was ruined at that point, right?” Ms. Estevao asked.
“I could understand that, yeah,” Ms. Ventura replied.
Joe Coscarelli and Olivia Bensimon contributed reporting.
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.
Thomas Fuller, a Page One Correspondent for The Times, writes and rewrites stories for the front page.
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