Diddy Trial Updates: Bombshell Court Moments, Kid Cudi to Freak Offs

Pop icon Britney Spears and actor Michael B. Jordan were both name-dropped on May 15, on Ventura’s third day of testimony.

During a cross-examination, Ventura was asked to tell the jury about the 21st birthday party Combs threw for her in 2007, at a club in Las Vegas.

The party was a significant moment in the Combs-Ventura story. Ventura testified Wednesday that the rapper, who recently signed her to his record label, gave her an uninvited kiss in a bathroom, sparking their relationship.

“I believe there were other celebrities there in attendance?” defense attorney Anna M. Estevao asked Ventura, who answered yes, there were.

“Sean was there, and he brought Dallas Austin, he brought Britney Spears,” Ventura said, referring to the “Oops!… I Did It Again” singer and the record producer. “I think those were the two people that stand out to me,” Ventura added.

Asked how a 21-year-old of limited fame was able to attract such big names to her party, Ventura credited Combs, saying, “That was all him.”

Jordan’s name came up as the cross-examination focused on 2015, when Combs became suspicious that she was having an affair with the actor.

“Is Michael B. Jordan a celebrity?” Estevao asked.

“I would say so,” Ventura answered, sounding surprised.

Ventura was not asked if the rumored affair actually happened.

Both Combs and Ventura were heavy opioid users, the R&B singer testified — and on one late night in February 2012, the pills he took made the rapper seriously ill, she said.

“Was that around the time that Whitney Houston died?” Estevao asked about the timing.

“Yes,” Ventura said.

That evening, the pair went to a sex club in San Bernardino, California, and then she went home, and Combs went to a party at the Playboy Mansion, Ventura told jurors.

“Well, 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,” Ventura testified.

There, she said, she learned that he had overdosed on whatever painkillers he had taken, she said.

On Ventura’s second day of testimony, she told jurors that Combs paid her $20 million to settle her civil suit against him in 2023.

Ventura testified to “spinning out” and suffering from “horrible flashbacks” in 2023, saying she once tried to walk into oncoming traffic but was stopped by her husband. After that, Ventura said she went to trauma therapy and rehab for drug addiction, and began writing a book about her experiences.

Ventura said she wrote the book so Combs could read it and understand the pain he put her through, but she said he didn’t take it seriously.

She later filed a lawsuit against Combs.

“I wanted to be compensated for the time, the pain, the many, many years of trying to fix my life,” Ventura said of her book.

Ventura said she wanted $30 million from Combs to purchase the rights to her book.

“I really didn’t do any research. I just picked a number that I felt like would alert him,” Ventura testified.

Ventura told jurors that she briefly dated rapper Kid Cudi, whose real name is Scott Mescudi, in 2011 and that it sent Combs into a violent rage.

Combs discovered the relationship during a freak off in Los Angeles when he went through Ventura’s phone, she testified.

“I just remember him putting like a wine bottle opener between his fingers and, like, lunging at me,” Ventura said, adding that Combs’ “eyes blacked out, super angry.”

“And I just had to get out of there,” she said. “It was actually another time I was able to get out of a freak off.”

When Ventura saw Combs at his home later that day she said he was “irate” and threatened to release freak off videos of her and “hurt Scott and I.”

On her way out, Ventura said Combs kicked her in the back so hard that she fell to the floor.

Ventura, whose lawsuit first suggested that Combs was responsible for blowing up a car that belonged to Kid Cudi in 2012, told jurors that Combs said Kid Cudi’s car “would be blown up” when they were out of the country.

“Sean wanted Scott’s friends to be there to see the car get blown up in the driveway,” she testified.

Prosecutors alleged in court papers that Combs ordered his underlings to torch a vehicle “by slicing open the car’s convertible top and dropping a Molotov cocktail inside the interior.”

Ventura, who dated Combs on and off from 2007 to 2018, is one of the key witnesses in the prosecution’s case. She described the “freak offs,” drug-fueled sex performances at the core of Combs’ indictment that prosecutors say Combs arranged, directed, and often electronically recorded.

In her opening statement on Monday, prosecutor Emily Johnson told jurors that Combs used “lies, drugs, threats, and violence to force and coerce” Ventura and later an anonymous Jane Doe into sex performances that would last for several days. Combs also referred to these events as “wild king nights” and “hotel nights.”

Johnson said Combs taught Ventura that “defying him could and often would end in violence” by brutally beating her for minor perceived infractions.

“He beat her when she didn’t answer the phone when he called. He beat her when she left a freak off without his permission. He beat her when he thought she took too long in the bathroom,” Johnson said.

When Ventura took the stand on Tuesday, she also testified that arguments with Combs would regularly result in physical abuse.

On Wednesday, Ventura described six separate times Combs’ attacks left her with injuries, with the most severe beating occurring in Los Angeles in 2009 following a party Combs had hosted at a club called Ace of Diamonds.

Ventura said she punched Combs in the face after he called her a “slut or a bitch” for talking to a record producer. Combs retaliated in the back seat of a chauffeured luxury vehicle by punching and kicking Ventura throughout a ten-minute ride to the rapper’s rented mansion, she said.

Ventura said she hid under the back seat to escape the attack.

“I was trying to cover my face,” Ventura said. “Because Sean was stomping on it with his foot.”

Ventura testified on Tuesday that she was initially nervous but felt a sense of responsibility to participate in Combs’ freak offs.

“I was just in love and wanted to make him happy,” Ventura told the jury.

Ventura testified that in 2007, Combs first proposed “this sexual encounter that he called voyeurism, where he would watch me have a sexual encounter with a third man, specifically another man.”

“I didn’t want to upset him if I said it scared me or if I said anything aside from, ‘OK, let’s try it,'” she said.

The prosecutors said in their opening statements that Combs eventually made it Ventura’s job to find and book escorts to participate in the sex marathons.

“Freak offs that were happening as often as once a week for days at a time. Meaning that for almost half of every week, Cassie was in a dark hotel room, high and awake for days, performing sex acts that she did not want to do on male escorts,” Johnson said.

Ventura testified on Tuesday that Combs would urinate and ask escorts to urinate on her during the freak offs.

“It was disgusting. It was too much. It was overwhelming,” she said. “I choked.”

In March 2024, the Department of Homeland Security raided Combs’ Los Angeles and Miami homes. Later that year, Combs’ indictment said that law enforcement seized “more than 1,000 bottles of baby oil and lubricant” during the raid.

During her testimony, Ventura said bottles of Johnson’s baby oil and Astroglide were used as lubricants during the freak offs.

“We poured it all over our bodies, they had to be glistening,” Ventura said. “It was always heated. Like, with the cap on, we’d put it in the sink with hot water and it’d be heated up.”

Ventura told jurors that Combs would sometimes order her to apply more baby oil during the freak offs.

“He would say, ‘You’re too dry, you need to put more oil on,’ or ‘you need to be glistening, you need to be shining.'”

Ventura testified that the freak offs would be “super pungent” because of all the oil, body odor, and candles.

“There was oil all over the walls, the door handles, the bed, the sheets,” she said.