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I was in the courtroom for Diddy’s trial. Cassie’s testimony was more graphic than I ever imagined.

May 17, 2025
in News
I was in the courtroom for Diddy’s trial. Cassie’s testimony was more graphic than I ever imagined.
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People traveled from other states to watch the Sean "Diddy" Combs trial in real life
I’ve been in the courtroom for a lot of major trials. The Sean “Diddy” Combs trial is unlike any other.

Lloyd Mitchell for BI

From the start of Sean “Diddy” Combs’ sex-trafficking trial, everyone was waiting for Cassie Ventura to appear. She was the star witness.

I expected Ventura’s testimony to be explosive. But it turned out to be more graphic than I ever imagined.

In the courtroom, I noticed the distress on the face of Ventura’s husband. His wife, who is eight months pregnant, was telling her alleged abuser and a room full of strangers about some of the worst moments in her life.

In September, federal prosecutors in Manhattan accused Combs of racketeering and sex trafficking. They say he used the vast power and resources of his record label and other businesses to arrange drug-fueled and baby oil-lubricated sexual encounters called “freak offs” with Ventura, other victims, and male escorts.

Combs pleaded not guilty and denies the sex-trafficking allegations, but he hasn’t quite denied all wrongdoing. His legal team said he participated in “mutual abuse” with Ventura, and that the two frequently fought physically. This was a domestic violence case, they argued — ugly, but not criminal sex trafficking.

In her testimony, Ventura talked about a messy, 11-year relationship during which she fought for scraps of Combs’ attention. He was often busy with other women and his various businesses, she said. Ventura participated in the freak offs out of love for Combs, she said, but they were never something she wanted.

The hip-hop mogul introduced her to the idea of freak offs about six months into their relationship, when she was 22 and owed him another nine albums as part of a record label deal, Ventura said. Combs would watch as Ventura would have sex with other men, who were paid thousands of dollars in cash, according to court testimony.

In text messages and emails shown as trial evidence, Ventura talked about arranging the freak offs, which required dropping by a Duane Reade to pick up baby oil, lubricant, candles, and condoms.

The freak offs could last up to four days, requiring drugs to maintain stamina, she said. They typically required up to 10 large bottles of baby oil, she testified. Everyone “had to be glistening,” as she described it. At one point, the judge stepped in to ask prosecutors to pull back from the deluge of baby oil questions.

The disturbing nature of the testimony was only heightened by Ventura’s appearance. She is due to have a baby in June and was visibly pregnant. One courtroom marshal said he was prepared to deliver her baby if the stress of testifying induced labor. I wasn’t sure if he was joking. One of the prosecutors urged the judge to require Combs’ lawyers to wrap up cross-examination. “We are afraid she could have the baby over the weekend,” she said.

Cassie Ventura’s testimony transfixed the courtroom

Over the years, I’ve reported on about a dozen trials and countless more court hearings. There were the uncomfortable benches of Donald Trump’s criminal trial. The rowdy fans at the R. Kelly Trial. The cold December mornings when I lined up for the Ghislaine Maxwell trial. The ultracompetitive Sam Bankman-Fried trial, where getting in line at 4 a.m. still wasn’t early enough to get inside the courtroom.

But nothing in my experience has compared to the Combs trial, which began Monday morning after a week of jury selection and is supposed to last two months.

A woman sleeping in line
People stayed in line overnight before the trial, hoping to make it into the courtroom.

Lloyd Mitchell for BI

Ever since Ventura accused Combs of sexual abuse in November 2023, Combs’ legal quagmire has been one of the biggest stories in the country. Combs paid Ventura $20 million to settle her case, but a flood of other accusers filed additional civil lawsuits against him. When prosecutors brought the criminal case against Combs, it was put on the fast track.

No longer the image of a pop star, Combs dresses for court like an office drone, wearing thin crewneck sweaters over white button-down shirts. He rarely betrays any emotion, occasionally nodding during his lawyers’ arguments or huddling with the attorneys beside him.

His large family, including his mother and seven children, has been in the courtroom to show their support. Every day, Combs flashes them heart symbols with his hands. Their expressions, during trial proceedings, have remained neutral. The gravity of the situation — Combs could spend the rest of his life in prison if convicted of all charges — is obvious.

Courtroom artist Christine Cornell outside the Sean "Diddy" Combs trial
During breaks, courtroom artist Christine Cornell took photos of her trial illustrations.

Lloyd Mitchell for BI

On the other side of the courtroom aisle are Ventura’s support group, which includes her husband, Alex Fine, and several relatives. At some of the more raw moments of Ventura’s testimony, Fine’s face looked visibly pained. When her texts with Combs about the freak offs were shown to the jury, he broke his gaze and looked at his lap.

As Ventura testified in graphic detail, the courtroom was rapt. She spoke in a faint, dispassionate voice.

The grim atmosphere made the otherwise unbelievable details of the trial feel upsetting rather than dramatic. On social media, these details fly by as jokes. For Ventura, they left scars. In February of 2023, years after she left Combs, Ventura couldn’t sleep, she testified.

“I couldn’t take the pain that I was in anymore, and so I just tried to walk out the front door into traffic,” she told the jury. “And my husband would not let me.”

‘I’ve been to a Diddy party’

On Monday, for opening statements, the line outside the lower Manhattan courthouse began the previous afternoon. Same Old Line Dudes, the standard-bearer line-sitting company for New York trials, declined to disclose the precise time their clients booked because “it’s very competitive,” a receptionist told me.

During lunch breaks, live-streamers went outside and updated their followers on what unfolded indoors. Christine Cornell, a courtroom sketch artist, took photos of her illustrations in natural sunlight to share them with the media. Vicky Perez, who had come to New York City from Connecticut to watch the trial’s opening day, said she’s a fan of Ventura, having purchased her first album when she was in the fifth grade. Perez wanted her to “get justice,” she said.

“I want to see his downfall,” she said of Combs.

Vicky Perez, who had come to New York City from Connecticut to watch the trial's opening day, was almost persuaded.
Vicky Perez attended the trial to show support for Cassie Ventura.

Lloyd Mitchell for BI

The scene overwhelmed even Dennis Byron, the editor in chief of the Hip-Hop Enquirer, who said he’s reported on the hip-hop scene for 35 years. He covered Comb’s career since he was an up-and-coming artist.

“I’ve been to a Diddy party,” he said.

“Not one of those parties,” he quickly clarified.

Byron — who wore a tweed vest and trousers in the May afternoon heat — said he’s attended and photographed Combs’ extravagant “White Parties,” where he took photos of the likes of Combs, Ventura, Kim Porter, and Jay-Z.

Dennis Byron, the editor-in-chief of the Hip-Hop Enquirer
Dennis Byron, editor in chief of the Hip-Hop Enquirer, has been chronicling Sean “Diddy” Combs’ career for decades.

Lloyd Mitchell for BI

These parties took on a new meaning following the indictment against Combs, where they’ve been widely re-interpreted as sex parties (virtually every single celebrity who has been asked about this denies they were sex parties). But celebrities have been having orgies forever, Byron said. He remembers hearing about them in the 1980s. Flying in escorts — as prosecutors said Combs did for freak offs — wasn’t anything new either, Byron said.

“Well, I never stayed for those,” Byron said. “I never stayed for those orgies. But I’m sure they happen. But I never seen them.”

Combs’ White Parties were meant to show off his power as “a tastemaker,” Byron said. Combs accrued cultural capital — something prosecutors later said he used to coerce his victims.

“Remember, that party was a regular party,” he said as I wrapped up our conversation. “Ain’t no party like a regular Diddy party.”

Combs’ lawyers acknowledge his flaws — but say he’s not a sex trafficker

Combs’ trial was taking place in the same 26th-floor courtroom that saw the trials of Sam Bankman-Fried and two of E. Jean Carroll’s lawsuits against Trump. (Bankman-Fried and Combs share a jail unit together; Trump is in the White House.) As with all federal court cases, there’s no broadcast or livestream.

Karen Agnifilo-Friedman, Luigi Mangione’s lead defense lawyer and the husband of Combs’ lead lawyer Mark Agnifilo, often showed up to watch. The court staff had also set up three overflow rooms for journalists and members of the public to watch the trial on a closed-circuit camera feed, plus two rooms for members of the in-house press like me.

Several people I spoke to said they were willing to keep an open mind, but believed it would be hard to shake the memory of watching the video of Combs beating Ventura and dragging her through a hotel hallway.

“I’m going to try to give him a fair shake, said Oota Ongo, a YouTuber who livestreamed himself walking around the courthouse after watching opening statements. “We all saw the Cassie tape. That Cassie tape is just something that I can’t get out of my head.”

Oota Ongo, influencer
Oota Ongo went outside during breaks in the trial to share updates with his YouTube followers.

Lloyd Mitchell for BI

Depending on the day, I alternated between the courtroom itself and a press room. When I checked out an overflow room one day, I spotted a prominent federal prosecutor who had put Bankman-Fried behind bars. He was paying close attention to Combs’ lawyer, Teny Gregagaros, giving Combs’ side of the story in an opening statement.

While Combs may have been an unpleasant, angry, jealous, and violent man — especially when drunk or high — he was not guilty of sex trafficking, Gregagos insisted. At most, he was responsible for domestic violence, she conceded.

“He is not charged with being mean,” Gregaros told the jurors. “He is not charged with being a jerk.”

The first witness was a security guard at the Intercontinental Hotel, who testified about the infamous video where Combs assaulted Ventura (Combs just wanted to get his phone back from her, his defense lawyers said).

Next, before Ventura, was a male dancer who said he acted as an escort. He testified about being asked to carefully urinate during sex.

“Apparently, I was doing it wrong because they both stopped me and told me that I was supposed to let a little out at a time and not go full, like, take a leak on her,” he said, in a quote that perhaps best encapsulated both the graphic nature of the trial testimony and how prosecutors say Combs intimately choreographed people around him to satisfy his own desires.

During Ventura’s cross-examination, Combs’ lawyers pulled up texts in which Ventura indicated she enjoyed the freak offs.

But Ventura, in her testimony earlier, said she just wanted to make Combs happy. She loved him. But she never wanted the freak offs, she said.

“It made me feel worthless,” Ventura testified. “Like I didn’t have anything else to offer him.”

The post I was in the courtroom for Diddy’s trial. Cassie’s testimony was more graphic than I ever imagined. appeared first on Business Insider.

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