Cassie Ventura, who dated Sean “Diddy” Combs for over a decade until 2018, appeared in court as the star witness during his high-profile sex trafficking trial.
The pregnant R&B singer took the stand this week to testify against the disgraced music mogul. Her harrowing testimony revealed graphic details on everything from freak-offs and drug use to the emotional and physical abuse she endured throughout their 11-year relationship.
Here’s a roundup of the most shocking bombshell moments of Ventura’s testimony during trial.
How Cassie’s relationship with Diddy started
The duo met when the Bad Boy Records founder signed then 19-year-old Ventura to record her first album with the label. The business relationship turned romantic on her 21st birthday when Combs kissed her during a trip to Las Vegas.
Ventura admitted she cried after the kiss because “there was a 17-year age difference.”
“I was really confused at the time, you know, new artist. I was pretty naïve she said on the stand.
She also revealed she wasn’t sober the first time they had sex.
“I was drinking wine, then started to take drugs, a blue dolphin ecstasy pill,” she said. “Sean gave it to me, I had never taken it before. I was just out of it, laughing, didn’t know what it was until a little bit later.”
Diddy’s “insanely jealous” behavior
The “Me & You” singer spoke about Diddy’s “insanely jealous” and controlling behaviors throughout their relationship.
Ventura said Combs would have his security guards keep an eye on her at all times and that he had keys to her apartment. She also told jurors he kept many guns in his homes and would force her to carry one for him as a fear tactic.
“Sean controlled a lot of my life, whether it was career, the way I dressed, everything,” she testified. “I just didn’t have much say in it at the time.”
Violence frequently occurred
Ventura said Diddy first got violent when she was 21, shortly after they became romantically involved in 2007.
“He hit me in the side of my head and I fell to the floor of the car,” she recalled.
The violence only continued from there, according to Ventura. When asked how often Combs physically assaulted her, she replied, “Too frequently.”
She said if she even so much as made the wrong expression, “the next thing [she] knew, [she] was getting hit in the face,” and that any attempt to fight back would only “make him more violent.”
Ventura detailed another alleged incident in 2009, during which Diddy attacked her for the entire length of a 10-minute car ride. She said she was punched and kicked during another beating in 2015 that left her with “black eyes” and “golf-ball sized knots” on her forehead.
She also described a 2016 incident at a Los Angeles hotel, footage of which was released by CNN last year and played in full for the jury.
This frame grab taken from hotel security camera video and aired by CNN appears to show Sean “Diddy” Combs attacking singer Cassie in a Los Angeles hotel hallway in March 2016. (Hotel Security Camera Video/CNN via AP) CNN via AP
Throughout the 15-minute surveillance video, Combs can be seen grabbing, kicking and dragging Ventura down the hallway of the InterContinental hotel before throwing a vase at her.
“He was yelling at me and threw it at me,” she recalled. “[He was saying] that I wasn’t going to leave him … that I couldn’t.”
Following the various assaults, Combs’ team would often set her up in hotels or lock her away at home to hide until her wounds healed, she said. Ventura testified that many people, including Combs’ security guards, drivers and assistants, were witness to the brutal attacks and did nothing to stop them.
How Cassie was introduced to freak-offs
Ventura said she was 22 when she was first asked to participate in one of Diddy’s infamous sex parties known as “freak-offs.”
“He described it as a fantasy he had where he would want to see me having sexual interactions with another male so he could watch,” she revealed, saying she was “confused” and “nervous” but afraid to say no out of fear he would react with violence.
Ventura said the freak-offs happened almost every week for the subsequent years “sometimes for days on end” and that she was at times beaten while taking part in the encounters.
During cross-examination, the defense pulled up pages upon pages of texts and emails sent between Ventura and Combs in attempt to establish that she wasn’t coerced into the orgies.
But despite texts such as “I’m always ready to freak off,” Ventura maintained she did not want to be involved from the beginning. Things only got worse as she grew exceedingly tired of being forced to have sex with male escorts.
“Nothing good comes out of [freak-offs] anymore. You treat me like you’re Ike Turner,” she texted Combs in 2017, referring to the abusive husband of Tina Turner.
Drug use during freak-offs
According to Ventura, Combs plied her with ecstasy and cocaine to keep her awake while performing sexual acts during freak-offs.
“I was high, so I didn’t feel much,” she tearfully said on the stand. “Did this really happen to me? I didn’t know what was going to happen after that, if we were going to do it more frequently. I said yes to more, I didn’t want to make him upset or angry.”
Cassie Ventura wipes tears from her eye while testifying in Manhattan federal court, Tuesday, May 13, 2025, in New York. (Elizabeth Williams via AP) Elizabeth Williams via AP
Ventura said she eventually developed a serious addiction to opiates, which she used to come down from the physical exertion involved in the freaks-offs and the depressive moods that followed.
She also claimed Combs was dependent on opiates for a period of time. She said he was hospitalized in 2012 following an overdose of painkillers at the Playboy Mansion.
Diddy forced a male escort to urinate in Cassie’s mouth
The 38-year-old spoke of a time when Combs told a male escort to urinate in her mouth during a freak-off.
“There was no conversation. It was a turn-on for him, so it happened,” she said. “I just felt humiliated. It was disgusting. It was too much. I choked. I didn’t want to be doing that. … Sean urinated on me at the same time.”
Ventura again described being high and unable to control the situation, particularly with “two men standing over you.”
Cassie was forced to have sex during her period
Ventura testified that Combs expected her to perform in the freak-offs even during her menstrual cycle.
“He wanted that and I did not want to do that,” she said on the stand. “Blood would get on the linens.”
She further described suffering numerous UTIs from the frequent orgies.
Diddy used freak-off videos to blackmail Cassie
According to Ventura, the freak-offs were often filmed without her consent, and Combs would later threaten to release the footage when he was angry or wanted her to behave a certain way.
“I just feared for my career. I feared for my family,” she said, adding that she’d do anything to prevent the videos from becoming public.
Diddy vowed to hurt Cassie and Kid Cudi
The R&B singer testified about her relationship with Scott Mescudi, better known as rapper Kid Cudi, revealing the pair briefly dated in 2011 during a time when things with Combs were “not in the greatest place.”
Upon learning of the romance, Combs allegedly told her “he was going to hurt” the two of them and blow up Cudi’s car.
“His eyes blacked out,” Ventura described of Combs’ rage.
In January 2012, police did in fact respond to a vehicle arson at Cudi’s address in L.A., where his car was found engulfed in flames by an “incendiary device.” No suspects were ever arrested for the fire.
Cassie claims Diddy raped her amid their breakup
After Ventura attempted to end the relationship in 2018, Combs allegedly raped her on the floor of her home, she testified on the stand.
“His eyes were black, he wasn’t himself, it was like somebody taking something from you,” she said, describing how she was crying and saying “no” during the attack.
Ventura confessed she was consensually intimate with Combs one more time before ending the relationship for good. When asked why she would voluntarily have sex with Combs after being raped, she admitted it was difficult to extricate herself from the relationship after nearly 11 years.
Diddy settled Cassie’s lawsuit for $20 million
The alleged rape was among the many accusations Ventura made in her bombshell lawsuit against Combs in late 2023.
The suit was settled just one day later for an undisclosed amount, with attorneys only confirming the pair reached a deal “to their mutual satisfaction.”
While on the stand, Ventura revealed she agreed to a settlement of $20 million.
Cassie Ventura, left, and Sean “Diddy” Combs appear at The Metropolitan Museum of Art’s Costume Institute benefit gala celebrating “China: Through the Looking Glass” in New York on May 4, 2015. (Photo by Charles Sykes/Invision/AP, File)
Cassie considered suicide after suffering flashbacks
Years after leaving Combs, debilitating flashbacks of the abuse led Ventura to consider ending her life.
“I didn’t want to be alive anymore at that point,” she said of having suicidal thoughts in 2023. “I couldn’t take the pain I was in.”
Ventura tearfully recalled one instance in March of that year when she “tried to walk out the front door into traffic” while her two daughters were asleep in the house.
Her husband, Alex Fine, who’s been supporting her in court, stopped her from walking out the door that night.