Diddy defense tries to trip Cassie with timeline testimony

MANHATTAN (CN) — Defense lawyers for Sean “Diddy” Combs continued to grill his ex-longtime girlfriend, singer Cassie Ventura, on cross-examination on Friday, questioning her recollection of the timing of when she says she had been raped by the Bad Boy CEO at the end of their relationship in 2018.

While Ventura recalled in civil lawsuit against Combs that rape occurred in September 2018 following a dinner at an Italian restaurant in Malibu, Combs’ attorney Anna Maria Estevao said Ventura told federal prosecutors the rape happened in August.

She testified Friday that Combs invited her to the Burning Man festival in Nevada’s Black Rock Desert in 2018 after they had broken up.

The desert arts festival, notorious for being a hedonistic carnival of psychedelic drugs, ran from Aug. 26 through Sep. 3 of that year.

She said she was already dating her now-husband Alex Fine at the time but joined Combs for dinner at an Italian Malibu restaurant to have a closure conversation to conclude their relationship.

Ventura recalled that Combs seemed different during the dinner. “He was acting strangely,” she said.

Ventura testified earlier in the trial on direct questioning that Combs raped her on the floor of her Los Angeles apartment after she broke up with him for good in 2018 over his infidelities.

Following the rape, Ventura says she took steps to completely separate herself from Combs, including by leaving the home that he paid for and returning the car he purchased for her.

On cross-examination, Ventura said she sex again with Combs during a consensual encounter after the rape in September*.* Ventura testified she received a FaceTime call from Fine at some point during that evening but did not answer.

Combs’ defense lawyers showed jurors text messages in evidence from Ventura to Combs, telling him after the encounter that she had a great time.

Combs also texted her around the same time: “I know I look bad to you. I could tell I didn’t turn you on yesterday. I fell off.”

Ventura testified Fine punched a wall after she told him Combs had raped her.

In redirect questioning that followed, Assistant U.S. Attorney Emily Johnson asked Ventura if she had “a clear memory of August 2018.”

“Not super clear, but clear enough,” she replied.

“Do you have any doubt that Sean raped you,” the prosecutor asked, overcoming an objection from Combs’ defense. “No,” Ventura replied.

Cassie finished her testimony shortly after 3 p.m. on Friday, her fourth day on the witness stand.

The first week of the trial saw opening arguments from both sides completed on Monday, before prosecutors called a former hotel security officer who responded to Combs and Ventura’s domestic violence episode that had spilled out from the bedroom of a “freak off” into a hallway of the InterContinental Hotel in Los Angeles in 2016.

Ventura testified she fled the hotel that day after Combs hit her in the eye at some point during the ecstasy-fueled sex marathon, giving her a black eye the weekend before her first major movie premiere.

Prosecutor then called male stripper Daniel Phillip, who testified that, starting in 2012, Combs paid him thousands of dollars to engage in baby oil-drenched sex acts with Ventura at various New York luxury hotels, while Combs watched and masturbated.

Former federal prosecutor Neama Rahmani told Courthouse News that Combs’ defense strategy is seeking to distinguish between physical and sexual violence, but it remains to be seen if the emails and text messages examined during cross-examination were enough to discredit Ventura.

“From the jump, the parties recognized that the case is about gender violence. That’s why the prosecution and defense chose to have a female deliver their opening statements and to have a female cross-examine Ventura,” said Rahmani, president of West Coast Trial Lawyers.

“Teny Geragos and Anna Estevao are well qualified, but they’re a lot less experienced than the other members of the defense team. Having younger females open and cross the victim in a sexual assault case is important for optics.”

“This also makes sense because Combs was caught on video beating Cassie,” Rahmani added. “Denying the physical assault happened would lose credibility with the jury, but Combs isn’t charged with assault, battery or domestic violence, so the defense isn’t conceding much.”

The defense theory is about consent, Rahmani says. “The defense is trying to build up the victims and argue that they voluntarily chose to participate in the freak offs,” he told Courthouse News.  “The prosecution argued that no one would consent to being drugged until they threw up, urinated on or forced to have sex when they’re on their period or have a UTI.”

Prosecutors have indicated one of the next two witnesses they intend to call to testify will be singer Dawn Richard, a former member of Danity Kane — the girl group Combs assembled on the third iteration of the MTV reality competition “Making the Band.”

Shortly before Combs was arrested in September 2024, Richard filed a civil lawsuit against him and his companies on counts of sex trafficking, battery and violations of the Victims of Gender-Motivated Violence Act.

In her 55-page complaint, Richard described a myriad of ways Combs abused her while she was part of his Danity Kane group and Diddy – Dirty Money trio. She claimed that Combs fostered a work environment that saw her frequently stripped down to her underwear while Combs touched her inappropriately.

“With no legitimate purpose, and without Ms. Richard’s consent, Mr. Combs caressed her buttocks to show the stylist where he wanted her high-waisted panties positioned, and attempted to touch her breasts, claiming to show the stylist where he wanted her bra straps to go,” Richard wrote in the suit.

Richard says she was present when Combs was introduced to Cassie for the first time, in or around 2006, when she would have been 20 years old.

“The moment Mr. Combs first saw Ms. Ventura, his demeanor noticeably shifted,” she wrote in her complaint. “Mr. Combs positioned himself directly in front of Ms. Ventura’s seat, invading her personal space, and fixated on her with an intense, unyielding stare, isolating her from the other people in the room, including Ms. Ventura’s then-boyfriend, music producer Ryan Leslie.”

Richard also recalled in her complaint having witnessed the music mogul punch, strangle and drag Cassie at Combs’ house in 2009, during the recording of Diddy – Dirty Money’s album “Last Train to Paris".

She said Combs then threatened her and bandmate Kalenna Harper to keep hush about the incident.

“This is normal, this was just a lover’s argument where no one was hurt … this is what love is,” she says Combs explained. “If you say anything, there will be consequences,” he warned.

She also alleged Combs further cautioned that “people end up missing.”

Combs, 55, is standing trial on a five-count indictment charging him with racketeering conspiracy, sex trafficking and transportation to engage in prostitution.

If he is convicted on all counts, he could face life in prison.

Combs’ mother, Janice, along with six of his children — Quincy, Justin, Christian, Chance, twins D’Lila and Jessie — have attended trial days during the first week.

His three daughters excused themselves from the courtroom during graphic testimony involving sexual encounters between their father and a male escort who was hired by Cassie ostensibly to perform a striptease and became a recurring “freak off” participant.

Combs’ extended family and entourage, on some trial days occupying two rows of the courtroom gallery, typically arrive at and exit from the courthouse together in a black Sprinter van without giving comments to reporters and spectators crowding the sidewalk.

The trial has attracted international media attention, in addition to dozens of independent reporters and streamers, who opine on the day’s proceedings into cellphone cameras outside of the courthouse.

A queue of professional line-sitters, many touting the #LineDudes company, assembles before dawn each day westward along Worth Street, holding spots for an hourly rate for media outlets who want seats in the courtroom.

The trial is expected to run up to eight weeks into early July.

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