After locking in the jury, the prosecution and defense jumped into opening statements in Sean Combs‘ trial. Cassie was prominently mentioned by both sides on day one. On Tuesday (May 13), Cassie took the stand against Diddy, as expected. There are no cameras in the courtroom for now, but illustrations are actually painting the picture! Here are a few things to know as we update you on Casandra Ventura‘s comments about her years-long ties to Combs.
As a reminder, prosecution is accusing the Bad Boy Records founder of orchestrating an empire of exploitation that forced women and others into drugged-up sex parties called “freak-offs.” Testimony in the trial began Monday. Prosecutors told jurors that, for years, Combs used his status as a powerful executive to coerce women into abusive sexual encounters and became violent if they refused. Lawyers for the three-time Grammy winner agreed that he could be violent. But they also said Combs never veered into sex trafficking and racketeering, telling jurors the sexual acts were consensual. Combs, 55, has pleaded not guilty. Sean Combs has been jailed in Brooklyn since his arrest in September. If convicted, he could get at least 15 years and up to life in prison.
On The Stand: Cassie Explains First Time Diddy Asked Her About A Freak-Off
On Tuesday morning, after some wrap-up testimony from Daniel Phillip, a ruling on Alex Fine’s presence in the courtroom, and a short break, Cassie took the stand at about 11:13 a.m. local NYC time. The singer has testified that she was in a relationship with Sean Combs for over 10 years. She admitted that their time together went from good times to arguments and physical altercations.
“If they were violent arguments, it would usually result in some sort of physical abuse and dragging, just different things,” Cassie said on the stand.
Casandra added that Diddy would “mash her head, drag her, kick her, and stomp her in the head when she was down,” as reported from TSR staff witnessing testimony live.
Cassie testified that Combs would mash her head, drag her, kick her, and stomp her in the head when she was down.
Asked how frequently Combs became violent with her, Cassie softly responded: “Too frequently.”
On the stand, Cassie has been taking deep breaths and pausing as she speaks, emotional from the start. She explained that Sean Combs “controlled” a lot in her life, from the way she dressed to “everything.” She added, “I just didn’t have much say in it at the time.”
Cassie testified that she was barely 22 when Sean Combs first asked her to join a “freak off.” At the time, she said she was “confused, nervous,” but “loved him very much.”
“I just remember my stomach falling to my butt. Just the nervousness and confusion in that moment,” Cassie testified about when Diddy first proposed the idea.
Additionally, she was worried about what would happen if she said no to him, ranging from violence to blackmail threats.
“Sean is a really polarizing person, also really charming,” Cassie, per the Associated Press. “It’s hard to really be able to decide in that moment what you need when he’s telling you what he wants. I just didn’t know. I didn’t know what would happen.”
In the 2016 viral hotel hallway video, Cassie said she and Diddy were engaging in a Freak-Off when she attempted to leave. Right before taking a court break, Cassie testified that the longest sexual party she was involved in lasted four days, with others lasting between 36 and 48 hours. “The freak offs became a job,” she later testified, highlighting the need for recovery from dehydration, tiredness, and drug use.
On The Stand: Singer Reveals When Diddy Relationship Turned Sexual
Cassie said that Diddy first kissed her when she was 21, on her birthday trip to Las Vegas, in his hotel bathroom suite. Before then, their relationship was platonic. After the kiss, the singer said she felt “really confused ” and “young.” After Vegas, Cassie said Diddy invited her to hotels in New York to discuss the music business. At one of those visits, she said on the stand that Diddy introduced her to the “idea of oral sex.” Up until that point, she was “sexually inexperienced,” as Sean Combs was 17 years older than her.
The first time they had sex was on a boat in Miami. She claims he introduced her to ecstasy for the first time, after she had sipped on wine in the afternoon. After they first had sex, Cassie said she thought they were in a monogamous relationship. “In hindsight, I know that wasn’t the case…Sean Combs had many girlfriends,” she testified.
While looking at the prosecution’s photos of them from the mid-2000s, Cassie admitted they were “having a good time” at first. She felt “enamored by him.” “It was really fun, at this point,” she added.
On The Stand: Cassie Shares Diddy Becoming Violent & Jealous
Eventually, the relationship got violent. Cassie started sniffling and dabbing her eyes when she explained how he became increasingly controlling and violent. She said he was insistent about phone calls and ringing down the staff when she didn’t answer.
“You make the wrong face and the next thing I knew I was getting hit in the face,” the singer said.
Cassie testified that Diddy would refer to himself in the third person, saying he’s “Puff Daddy” who has “many rules” and “likes the company of women.” She also recalled that he denied “dealing” with anyone else. “It’s just us,”she said.
The prosecution said Diddy rented apartments for Cassie near his homes in New York and Los Angeles to keep tabs on her. He allegedly also created his own set of keys and dropped by unannounced. In Manhattan, she lived a few blocks away, while in L.A., she was a three-minute drive from him—close enough to get there by golf cart.
Cassie testified that Diddy kept close tabs on her, with prosecutors highlighting the control he allegedly had over her life.
She said he paid her rent in NYC and LA, had his own keys, and made “a lot of unannounced visits.”
On The Stand: Cassie Shares Story Involving Suge Knight
The ITSR staff in the courtroom reports that Cassie confirmed Diddy once freaked out about his bodyguard sharing Suge Knight’s whereabouts. Both men allegedly grabbed guns and left in dark clothing, Cassie testified, adding that she was crying and screaming for him not to go. But Diddy allegedly left anyway and came back later. However, Cassie didn’t share whether Diddy saw Suge Knight at the diner.
Cassie said Diddy later returned, but she didn’t say if he told her what happened. It’s unclear if he ended up seeing Knight at the diner.
On The Stand: Cassie Shares How She Felt About The Freak-Offs
About a year into the sexual relationship, Cassie experienced her first “freak-off.” She was 22, per her testimony, and it was about 2008. It involved a male stripper who came to their home, a few months after he told her he was into “voyeurism.” The act consists of a person being attracted to watching another person engage in sensual or sexual acts.
During that time, Diddy paid for luxuries like cars and gave her cash, but Cassie said he also took it away at leisure. She revealed that he also instructed staff whom she encountered daily to do so, name-dropping Kristina Khorram “KK,” Ms.Fletcher, and D-Roc, from Diddy’s security team. When Combs didn’t strip her of material things, Cassie said he took away her “self-confidence.”
Ultimately, though, Cassie testified that she didn’t want to upset or anger Diddy or make him “regret” telling her “about this experience that was so personal.” When asked whether she enjoyed anything about the freak-off, while teary and emotional, she said, “The time spent with him.” Again, she confirmed that the freak-offs were frequent, weekly. The last one she was in happened in 2017 or 2018, Cassie recalled.
Wiping away tears, she explained that those encounters provided some of her only one-on-one time with Diddy. Cassie said she was engaging in “freak offs” weekly. The final one occurred in 2017 or 2018.
Later in the testimony, Cassie said she can’t recall all the freak-offs because there were too many. She testified that she wanted them to end but feared being replaced or angering Combs.
Cassie testified that she couldn’t recall all of the “freak offs” because there were too many. She said she wanted to stop, describing the experiences as humiliating and emotionally overwhelming, breaking down in tears on the stand. Although she told Combs she didn’t want to…
Prosecutors also asked the singer why she agreed to participate in the freak-offs, and Cassie responded that she wanted to make Diddy happy.
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On The Stand: Diddy Did LOVE His Baby Oil, Cassie Confirms
Cassie also discussed Diddy’s affection for baby oil during the “very choreographed experience.” The oil would be heated in sinks of hot water and used liberally. The singer said Combs preferred her glistening and often called her out when she “looked dry,” ordering her to moisturize. She recalled a time when he allegedly ordered a blow-up pool filled with baby oil and lubricants for a hotel “freak off.” According to Cassie, up to 10 bottles of baby oil would be used in freak-offs.
She said she ingested ecstasy and alcohol before the “freak offs” and wore a “masquerade mask” on Diddy’s order. Every session of this voyerism lasted until the escorts involved finished sexually, Cassie said.
“It was such a mess,” she said. “It was like, ‘What are we doing?’”
Prosecutor Emily Johnson repeatedly asked Cassie “Whose decision was it?” Each time, Cassie responded, “Sean.” She testified that it was his decision to involve her in “freak offs,” use baby oil and male sex workers, pour candle wax on her, and engage in other acts.
On The Stand: Cassie Clears The Air On How She Felt About The Urine
While testifying, Cassie cleared up any notions that she enjoyed the urine aspects of the “freak offs.” She called the experience “disgusting” and admitted to choking once because too much was in her mouth. “No one could think I wanted it,” the singer testified.
In court, when asked by the prosecutor if she wanted to be urinated on, Cassie firmly replied “No” calling the experience “disgusting” and saying she choked due to too much urine in her mouth. “No one could think I wanted it.” she said.
She added that she did not want anyone to urinate on her, but that it happened “often enough.”
She stated Diddy urinated on her and emphasized, “I didn't want anyone to urinate on me.” Cassie said it happened “often enough.” When asked about hotel damages, she identified the InterContinental in New York as the most expensive, noting it had to redecorate the entire room.
On The Stand: Email Exchange Reveals Cassie Called Diddy Pop Pop, Used Drugs At Freak Offs
As her testimony continued, more details came to light about Cassie and Diddy’s alleged submissive-dominant relationship. An email exchange introduced in court revealed Cassie referring to Combs as Pop Pop after he allegedly asked her what she called her grandfather. Now, she sees that the request was “disrespectful.”
She also responded to the prosecution questioning why she once sent Diddy a message saying she “really needs to f**k.” She said she wanted to be with him at the time.
The prosecution asked what she believed the message meant. Cassie said she thought he understood she didn’t want to keep doing it — but she pulled back out of fear, adding that her fear stemmed from his past violent behavior.
Cassie also confirmed that the topic was drug use in an email exchange between her and Diddy, presented in court. She admitted to consuming drugs like Special K, GHB, mushrooms, ecstasy, and MDMA to dissociate from the “freak offs.”
Cassie testified that she used drugs at every “freak off” to dissociate and feel emotionless, naming substances like Special K, GHB, mushrooms, ecstasy, and MDMA. She said Combs also used drugs, and sometimes the escorts did too. In an email exchange, Cassie confirmed they were…
Cassie also alleged that Diddy forced her to continue performing sexual acts even when the drugs made her nauseous or throw up.
Cassie testified that she did not want to continue having intercourse when she felt like vomiting. She described the effects of various drugs: GHB made her feel drunk and tipsy, cocaine made her heart race (which she didn’t like), and mushrooms caused hallucinations, making the…
Alex Fine Seen Leaving Courthouse As Cassie Testimony Ends On May 13
Before Cassie’s testimony ended on Tuesday (May 13), she spoke about Diddy violently beating her when she tried to leave a freak off early to attend a premiere. She said Combs threw her to the ground and grabbed her by her neck and hoodie. Prosecution showed footage to back up her testimony.
Testimony ended shortly afterward. Cassie is expected to return to the stand on Wednesday, May 14, at 9:30 a.m. local time for more questions from the prosecution. Afterward, cross-examination from Diddy’s lawyers will begin.
Testimony ends for the day and Cassie is set to return to the witness stand on Wednesday at 9:30 a.m. for more questioning from prosecutors. Assistant U.S. Attorney Emily Johnson said she expects to finish her questioning on Wednesday. After that, Diddy’s lawyers will have a…
After the testimony ended for the day, Alex Fine was spotted leaving the courthouse on video. He will soon have to sit out testimony when Cassie speaks about a 2018 rape, as he might be called as a witness. However, he was allowed to sit through today’s proceedings. The prosecution had argued that Alex Fine was supporting Cassie, who is pregnant with their third child.
What The Prosecution Versus Defense Said In Opening Statements
Assistant U.S. Attorney Emily Johnson said Diddy beat Cassie often and with little provocation. Johnson added that he threatened to ruin her music career by releasing videos of her engaging in sexual acts with male escorts during encounters he arranged. Combs allegedly sexually exploited and beat other women, including a woman identified only as Jane. Combs is accused of attacking Jane after she confronted him about the “freak-offs.”
Cassie’s lawsuit against Combs was settled within hours, followed by dozens of similar legal claims, and touched off a criminal investigation.
An attorney for Combs, Teny Geragos, told the jury Combs’ accusers were after his money, adding that jurors might think he’s a “jerk” and might not condone his “kinky sex,” but that “he’s not charged with being a jerk.”
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What Have The Witnesses Testified About Cassie So Far?
Cassie has been at the center of Combs’ legal woes since 2023. She sued him in November of that year, alleging years of abuse. A surveillance video made public last year showed Combs beating her at a Los Angeles hotel in 2016. CNN aired the footage last year, leading Combs to apologize. The video shows Combs wearing only a white towel, punching, kicking, and dragging Cassie in a hotel hallway. Jurors watched it on Monday.
Also, Israel Florez testified Monday that he came across Combs while responding to a call about a woman in distress. Florez worked as a former security officer at the hotel. He testified that he found Combs sitting in a chair with “a devilish stare.” Florez said Combs offered him a stack of money and said, “Don’t tell nobody.” Florez said he refused the cash and told Combs, “I don’t want your money. Just go back into your room.”
Judge Addresses Media Request To View Cassie & Jane In "Freak Offs" Videos With Jury
The Shade Room is on site at the courthouse. Day two of testimony is picking up with the judge addressing whether to grant requests from the media to view the “freak offs” videos that the prosecution will present as evidence. Judge Arun Subramanian is giving the trial until tomorrow to submit arguments on it, meaning that even with Cassie’s testimonies, the jury might not see those videos today.
Right now, no photos or videos are allowed from the courtroom—just illustrations.
Judge Arun Subramanian says he’s inclined to grant a request by media organizations to view what a defense lawyer described as pornographic videos that will be shown to the jury as evidence in the case.
But he’s giving the parties another day to make submissions on the matter.…
Cassandra Santiago is a multimedia journalist, editor, and editorial strategist with over a decade of experience shaping conversations across arts, entertainment, culture, and global news. A graduate of the University of Iowa, she has built a cross-platform career spanning newspapers, magazines, radio, and digital media.
She joined The Shade Room five years ago and currently serves as a Senior Editor, where she leads editorial direction, oversees exclusive coverage, and trains and edits a team of writers. Cassandra has played a key role in developing high-impact content and editorial strategies for an audience of more than 30 million, contributing to platform growth, engagement, and monetization across multiple channels. In addition to her leadership role, she remains a daily contributor, with her articles generating more than 41 million views since 2023.
Beyond The Shade Room, Cassandra offers freelance social media strategy services, speaks on the influence and impact of Black media at public panels, and owns Did It For You, an event design company in the DC, Maryland, and Virginia area. She is Poynter Institute–certified and was named to the DMV’s 35 Under 35 list in 2024.
