“You and Sean Combs were in love for 11 years, right?” defense lawyer Anna Estevao poignantly asked Cassie Ventura today at the beginning of her cross-examination of the former longterm girlfriend of the ‘All About the Benjamins’ performer in Combs’ sex-trafficking trial. After the heavily pregnant Ventura responded in the affirmative, Estevao gently added, “You knew the Sean that he didn’t want anybody else to see but you?”
Ventura admitted that even though she found Combs’ charismatic big personality to be”scary” when they first met, she felt she discovered the so-called “real” Sean Combs underneath his public perpetual hypeman persona . He was “very sweet” and “attentive,” Ventura said, in many ways reiterating testimony she gave while under questioning from the prosecution earlier this week.
More from Deadline
It should be noted that the feds want to paint a portrait of Combs as upstanding in the first months he and Ventura were together to illustrate how he always intended to bend the then 19-year-old singer to his will and desires. For the defense, the reasoning is clearly the opposite. Their goal is to convince the jurors that as distasteful as it could sometimes be, Ventura and Combs had a genuine relationship between complicated people with non-traditional desires and turn-ons, but with no coercive undercurrents
“To make him happy, you told him that you wanted to do ‘freak-offs,’” the defense attorney queried, going to the escort and chemically enhanced sex sessions that Combs asked the often jealous Ventura to participate in about a year into their relationship that is at the core of the feds’ case.
“There’s a lot more to that,” Ventura said.
At that point, Ventura directly asked Judge Arun Subramanian for a break in the proceedings. At the time the witness requested the pause, the court was looking at a series of explicit correspondence between Combs and Ventura.
Less than 24 hours after Ventura tearfully told the jury in the high-profile trial about being raped in 2018 by Diddy after they broke up, the singer Wednesday faced what is sure to be in-depth grilling from the defense team. Setting the stage, Ventura was asked earlier Thursday if she felt that she was “special” to the much-accused Bad Boy Records founder during the years they were together. The witness very quietly replied: “No, I don’t think I always knew.”
The intricacy of Combs and Ventura’s 2007 – 2018 relationship became evident when Estevao stated: “So when he cheated on you, it really hurt?” Looking out into the packed lower Manhattan federal courtroom, the eight-months pregnant Ventura responded: “I would say not every time.”
On the fourth day of the trial, Ventura’s questioning by ex-prosecutor Estevao follows a grueling day of testimony Tuesday that found the ‘Me & U’ singer frequently in tears, especially as she described an alleged 2018 rape by Diddy months after the couple had broken up.
The assault occurred on the living room floor of Ventura’s LA apartment. Combs had driven the singer home after the duo had gone for what the witness called a “closure conversation” and pleasant dinner in Malibu. Barely holding on to her composure and asking for a break in the proceedings soon afterwards, Ventura detailed how she was screaming “No!” and crying, but the “eyes black” Combs didn’t stop or seem to care.
“It’s like someone taking something from you,” Ventura stated, while also admitting to Assistant U.S. Attorney Emily Johnson that she later consensually had sex with Combs one more time after the alleged rape.
In that vein, the defense Thursday quickly leaned into their primary argument that Combs and Ventura were always consenting adults and Ventura was never forced to do anything she didn’t agree to, no matter how kinky or out of control their relationship was. Tho establish that stance, this morning, defense lawyer Estevao pulled up warm, gushing and also lurid emails from both Combs and Ventura from the early days of the couple’s time together.
Outside the Sean “Diddy” Combs’ trial at Manhattan Federal Court on May 15, 2025 (Photo by John Lamparski/Getty Images)
Kindly in nature from the start, because there really is no other way to question Ventura right now with all she has testified so far, the cross-examination by the Marc Agnifilo, Teny Geragos and Brian Steel-led defense of Ventura is expected to continue Friday and maybe even into early next week. Probably the most important witness of the prosecution’s case, Ventura was called as to testify right from the near start of the trial in part because of the advanced stage of her pregnancy.
This criminal trial of Combs began in great part with his arrest last September on charges of racketeering, sex trafficking, transportation to engage in prostitution and more.
If found guilty by the 12-person jury in court now, that since amended indictment could see the 55-year-old ‘I’ll Be Missing You’ performer behind bars for the rest of his life. At the same time, with his much mentioned allegedly enabling inner circle not defendants in this case, Combs faces dozens of civil case, including one filed earlier this week that mocks the Grammy winner’s genitals as it accuses him of raping a woman in his NYC apartment in July 2001. Repeatedly denied bail and incarcerated in Brooklyn’s Metropolitan Detention Center since last fall in this criminal case, Combs has also asserted he is not guilty of anything more than an unconventional lifestyle with other consenting adults, regardless of what the police, the Department of Justice, some ex-staffers, or any of his accusers say.
In so many ways, with cameos of sorts by Death Row Records founder and Combs rival Suge Knight, Prince, and Ventura’s short term boyfriend Kid Cudi, it was the complexity of star witness Ventura’s second day of testimony on Wednesday that was so powerful.
Janice Combs, mother of Sean Combs, arrives in the rain during Combs’ trial at Manhattan Federal Court on May 14, 2025 (Photo by Spencer Platt/Getty Images)
Yes, with a sweater wearing Combs, his mother and other members of his family just a few feet away in Judge Subramanian’s courtroom, she revealed the $20 million settlement she received from Combs after suing him in late 2023 for abuse and assault. Yes, Ventura revealed her own infidelities and drug use in the relationship and how she entered a rehab and trauma therapy program a couple of years ago after “spinning out” and contemplating suicide. Yes, she revealed Combs extensive threats (some of which may have borne fruition) against Cudi when Ventura was with the latter.
However, devolving into what Ventura herself called “degradation,” and injuries physical and psychological she experienced during the 11-year relationship, time and time again she still expressed the love she had for Combs despite the horrors, “freak-offs” and relentless violence and manipulation he seemingly subjected her to.
Explaining her decision to have sex with her now-ex Combs after he raped her, Ventura said in a steady but quiet voice, “We’d been together for 10 years and you just don’t turn that off.”
Having already acquiesced to their client being a domestic violence perpetrator and not great guy, the defense made it clear even before this trial began this week that is exactly that sentiment of the deep ties of the relationship they plan to focus on. Specifically, as the court saw in the beginning of cross-examination, that the self-described “toxic relationship” Combs and Ventura had was a two-way street and, even with Combs strong personality, to put it mildly, Ventura made her own choices and was a consenting adult to all and everything that went on, as sordid as it sometimes became.
To that, even as pregnant as current married mother of two Ventura is now, her words of love to Combs, her admitted agreement, as least initially, with the male escorts of “freak-offs,” the video footage of those marathon drug juiced session and the numerous text exchanges between the two organizing those session and the aftermath, even if it was all just to keep Combs happy, tell a tale of their own if you adopt a certain POV. It is those words, those actions that could prove the high-priced defense’s best path to a not guilty verdict for their not guilty pleading and plea deal rejecting client by the end of this eight to 10 week-long trial.
That strategy is reliant, however, on the jurors to some degree not believing their eyes.
Yesterday saw the panel shown a series of photographs from the “freak-offs. Photographs, not revealed to the public or media in the courtroom, that clearly shocked or surprised a number of jurors. Even before that prosecution carefully planned by the jarring display on Wednesday there was the repeated viewings in court of 2026 hotel security footage of a freak-off in action, to some degree. The stark nine-year old video from L.A.’s InterContinental Hotel, which, CNN obtained and broadcast last spring, shows a half-naked Combs beating and kicking his then-girlfriend in the hall and dragging her back to their room. Once hotel security arrive, Combs tries unsuccessful to convince Ventura not to leave, which, in possession of her phone and other essentials, she eventually does.
Sean ‘Diddy’ Combs physically assaulting Cassie Ventura in 2016
Last year, Combs, who bought for over $50,000 what he thought was the only copy of the footage, took to social media to apologize for what he did in 2016, Yet, in the past few months that apology has been deleted, and the defense disputed the feds reading of the events on the video. In her May 12 opening statement, the defense’s Geragos took a different tone, and used the video as an example of Combs committing domestic violence, but not the criminal charges the government have gone with.
Even with former employees of Combs and other women who say the one-time mini-mogul abused and assaulted them expected as witnesses (though Victim-3 has still not be located by the U.S. Attorney’s office), the judge has promised to wrap the matter up for the non-sequestered jury before the July 4th holiday. To meet that goal, starting next week, the court will go to a 9 a.m. to 3 p.m. ET schedule shorter breaks.
Best of Deadline
Sign up for Deadline’s Newsletter. For the latest news, follow us on Facebook, Twitter, and Instagram.
