UPDATE, 2:12 pm: From Ecstasy, MDMA, opiates, GBH and more, there was a lot of drug use during Sean Combs and Cassie Ventura’s self-described “toxic relationship,” especially during the long “freak-off” sex sessions. Even more than past testimony, there was a lot of talk about drugs today during the defense’s cross-examination of Diddy’s former girlfriend.
A lot of that material had come out already before the trial, in the opening statement from Combs’ legal team, and during the prosecution’s questioning of Ventura on Tuesday and Wednesday. Yet, in this war of coercion vs consent, as defense lawyer Anna Estevao attempted to establish that Ventura was not only an approving adult and not a victim in her admittedly deprived relationship with Combs, but often the initiator in the drug use, some new drug details were revealed.
In early 2012, Combs ended up in an L.A. hospital after overdosing during a party at the then Hugh Hefner-owned Playboy Mansion. Also, the defense now are suggesting that Combs was in the midst of a opiate withdrawal during the time of the harrowing security camera footage of the mini-mogul going ballistic as Ventura attempted to escape in the hallway of an upmarket L.A. hotel in March 2016.
RELATED: Cassie Ventura Got $20M From Sean Combs In 2023 Settlement, She Reveals In Trial Testimony
For the first instance, the couple were together that February night 13 years ago for yet another drug enhanced “freak-off” with a male escort having sex with Ventura, while Combs, as usual, watched, choregraphed and masturbated. They went to a sex club next, but Ventura didn’t head afterwards over to the then Hugh Hefner-owned manor. Hours later she did however get Combs to medical help where she learned he had OD’d.
“From what he told me, he took a very strong opiate that night, but we didn’t know what was happening, so we took him to the hospital,” she explained as Combs sat nearby in the relatively snug courtroom.
Piling on the defense’s contention that the effects of heavy drug use and extremely jealousy, on both the part of the sexually consenting Ventura and Combs, were the true deficits in their decade-long relationship, the now much seen 2016 occurrence at the InterContinental hotel was framed in a new context Thursday. Scrolling through text messages from March 3, 2016, Estevao indicated that Combs’ complaints of sickness and more were the result of opiate withdrawal. Conceding Combs was ill at the time, Ventura never denied nor confirmed if her then-boyfriend was crashing from his heavy drug use or not.
Drugs also were a topic when Estevao tried to get Ventura to admit she never actually saw Combs’ supposedly dangling her friend Bryana “Bana” Bongolan off the 17th floor balcony of her L.A. high-rise in September 2016. The incident was brought up by the prosecution on Wednesday, with a photo of the blue-haired fashion designer shown in court. Filed in late November 2024, Bongolan has an ongoing $10 million suit against the self-described “motherf*cking devil” Combs over the incident.
Citing a text Ventura sent that day almost nine years ago to Combs staffer Kristina Khorram about what happened, Estevao asked, “isn’t it true you learned about this incident after the fact?” Indignantly, Ventura snapped back: “I saw what I saw.” She also acknowledged she couldn’t remember if it was because of drugs or not that she was asleep that day. Yesterday Ventura told the court that she woke up to see Bongolan being pulled over the balcony by Combs and then tossed around into patio furniture.
Besides Ventura now answering questions from the defense as opposed to the prosecution, Thursday also saw a change in the lower Manhattan courtroom itself. Earlier in the week, Judge Subramanian rejected requests by media outlets to have some degree of access to the sealed overtly explicit evidence of photographs and videos from the “freak-offs.” At the time, he reiterated the “freak-offs” evidence would remain sealed and only the jury and the witness would see them.
On Wednesday, as that material was first introduced, only the jurors (some of whom were taken aback by what was in front of them) and Ventura saw the photos – though the courtroom heard them described in broad terms by Assistant U.S. Attorney Emily Johnson. Today, covers were put up around the jurors’ screens so the material on them could only be seen by the juror sitting right in front of them.
Additionally, to streamline things and keep Judge Subramanian’s pledge to have the nearly ready-to-give-birth Ventura’s testimony concluded by mid-day Friday, the witness was provided with an iPad to look through evidence and more. To that, Ventura and defense lawyer Estevao had some friction when in the midst of a long section of the day going over email and text correspondence, the witness made it evident she didn’t like the manner things were going.
“This isn’t about what I feel is relevant right now, right, because there’s a lot we skipped over,” Ventura said, to be ignored by the defense attorney.
As always, Combs was in the courtroom Thursday, sitting at the defense table and fairly close to Ventura. In sweaters and button-down shirts, the white-haired Combs looks more old Dad or young grandfather than a larger-than-life former hip hop superstar.
Over the past three days, Diddy has been waving and greeting friends, family and attorneys at the beginning of the day and during breaks. Several times over the first few hours of Ventura’s testimony on May 13, he became quite animated, jerking his head back on occasion. Throughout, the two days the prosecution questioned the witness, Combs and Ventura never seemed to make eye-contact.
The two didn’t seem to make direct eye-contact Thursday, but Combs very clearly had his eye on what was going on. In the morning and afternoon sessions, as drugs, Ventura’s relationship with Kid Cudi, and a brief 2015 relationship with then Creed star Michael B. Jordan and other matters came up, Combs was repeatedly passing Post-It notes to members of his defense team. During one break, the defendant had a short conversation with Estevao in the courtroom as the attorney prepared for further cross-examination of Ventura.
Ventura’s cross-examination will continue Friday morning. If Judge Subramanian can keep the trial to his schedule, the very pregnant singer will be out of the witness box by mid-day tomorrow. At the end of Thursday’s session, the prosecution told the judge that their next witness will be Dawn Richard, one of the singers from the Diddy fronted MTV series Making the Band. In September last year, right around the time Combs was arrested in his criminal case, Richard sued her past producer for rape and more. That civil case is ongoing.
The criminal trial itself is anticipated to run until close to the July 4th holiday.
PREVIOUSLY, 7:44 am: “You and Sean Combs were in love for 11 years, right?” defense lawyer Anna Estevao poignantly asked Cassie Ventura on Thursday at the beginning of her cross-examination of Combs’ former long-term girlfriend in his sex-trafficking trial. After 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 hype-man 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.
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.
Back in the witness box after about 15 minutes, Ventura, who is pregnant, had a moment of levity in what has been an unsurprisingly bleak proceeding for the most part so far this week. She seemed to laugh a little bit as Estevao read aloud an effusive email from the early days in 2007 of the couple’s relationship. On the other hand, other correspondence was introduced that dealt with Ventura’s opiate use and the ever expanding “freak-offs” that came to dominate the relationship with Combs.
Perhaps more telling of how hardball the defense intends to be, the issue of the $20 million settlement with Combs that came out of Ventura’s November 2023 rape lawsuit entered Thursday’s testimony briefly.
Shifting momentarily from her relatively moderate stance of the first part of the morning, Estevao bluntly asked Ventura if “you understood that his career was ruined at that point” Replying just as bluntly, Ventura said: “I could understand that, yeah.”
Later, in a discussion about the couple’s drug use during the “freak-offs” and otherwise over their years together, Estevao wondered if Ventura considered Combs a “high-functioning addict.” On, the follow up of what the endlessly entrepreneurial Combs was hooked on, Ventura gave it a one-word answer: “Success.”
RELATED: Cassie Ventura Got $20M From Sean Combs In 2023 Settlement, She Reveals In Trial Testimony
As the morning made obvious, 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 Thursday faced what is sure to be in-depth grilling from the defense team. Setting the stage, Ventura was asked earlier today 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-federal defender 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 L.A. 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. To 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.
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 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 cases, 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.
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 the 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 sessions and the numerous text exchanges between the two organizing those sessions 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 the panel was 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 carefully planned jarring display by the prosecution on Wednesday, there were 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 unsuccessfully to convince Ventura not to leave, which, in possession of her phone and other essentials, she eventually does.
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 still has 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 with shorter breaks.
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