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

May 17, 2025 Stan

The R&B singer Cassie Ventura — Sean “Diddy” Combs’ ex-girlfriend and the catalyst for his public downfall — has testified this week about humiliating sexual abuse she says she endured throughout their 11-year relationship.

Combs was arrested in September on federal charges of racketeering conspiracy, sex trafficking, and transportation to engage in prostitution — the culmination of months of lawsuits and public accusations of sexual assault and other misconduct.

It was Ventura’s November 2023 lawsuit that began this avalanche of accusations. Filed eight months before the criminal charges, it accused the hip-hop mogul of of rape, physical abuse, and controlling her during their relationship.

Ventura’s lawsuit settled for $20 million a day later — and she now front-and-center in his life once again, as the star prosecution witness at Combs’ federal trial.

Combs has denied all wrongdoing. The music tycoon is arguing through his defense team that all sexual encounters were consensual, including the drug-fueled, days-long “freak off” sex parties at the center of the trial. The defense also argues that any violence fell far short of sex trafficking and that his accusers have a financial motive to implicate him.

Here are some of the most striking moments from the trial so far.

A brutal beating, a threat, and flowers

Danity Kane singer Dawn Richard was the fifth prosecution witness, and her testimony on Friday alleged that in 2009, Combs brutally beat Ventura after she took too long to cook him dinner.

“Where’s my fucking egg?” Richard recounted Combs shouting in 2009, as he stormed into the kitchen of his rented Los Angeles mansion.

“He took the skillet with the eggs in it and tried to hit her in the head and she fell to the ground,” Richard testified.

Ventura cowered on the floor “in a fetal position” as Combs punched her and kicked her, she said. Then he dragged her upstairs by her hair, she said, adding that she the heard the sound of screaming and breaking glass from the third floor.

The next day, Combs called Ventura and Richard into the mansion’s first floor recording studio.

“He said that what we saw was passion, and it was what lovers in a relationship do,” Richard said.

Ventura “was OK and it was best if we didn’t say anything — that people go missing and he was trying to take us to the top,” she recounted Combs saying. “And then he gave us flowers.”

The details in the testimony came as a surprise to lead defense attorney Marc Agnifilo, who called it prejudicial and “just a drop dead lie.”

“It didn’t happen,” the lawyer complained to the judge. “And the reason we know it didn’t happen is that Ms. Ventura didn’t talk about it” during her four days on the witness stand.

Cassie’s big settlement after that infamous hallway-beatdown video

In some of her final moments on the witness stand, Ventura was asked by the defense about a legal settlement that she said she is on the verge of receiving from the InterContinental hotel in Century City, Los Angeles.

“I think it was $10 million,” Ventura said of the settlement, hesitating when asked for the total amount agreed to.

The InterContinental is where security cameras captured Combs beating Ventura in a hallway in 2016, as she tried to flee what prosecutors say was a one of Combs’ “freak offs.”

It’s was the second big-money settlement revealed in Ventura’s testimony. She also told jurors that Combs paid her $20 million to settle her civil lawsuit against him in 2023.

The surprising things Combs kept in his luxury NYC hotel room while waiting to be arrested

The prosecution’s fourth witness took the witness stand briefly on Friday, to detail what she and other Homeland Security investigators found inside Combs’ suite at the Park Hyatt New York after his September arrest.

Combs had checked into the luxury Midtown hotel, his lawyers have said, in case federal prosecutors in Manhattan had asked him to surrender voluntarily.

Special Agent Yasin Binda told the Combs jury she photographed what her colleagues found inside the room.

Those items included a clear plastic bag of baby oil bottles found inside a duffle bag. There were three more bottles of baby oil in his bathtub, alongside two bottles of personal lubricant.

Two more bottles of lubricant were recovered from a nightstand drawer, next to a prescription pill bottle she said held two small baggies containing a pink powder.

On the living room floor was a large blue party light of the kind Ventura testified were used to illuminate freak offs.

Similar bags of pink powder have previously been seized from Combs and tested positive for ecstasy and other drugs, a prosecutor had said in court the day after Combs was arrested.

“While he is sitting in a hotel, waiting to be arrested on federal charges, at a time when he should be on his very, very best behavior, he had what appears to be narcotics at his hotel room,” a prosecutor told the judge at the time.

Britney Spears and Michael B. Jordan became the biggest celebrity mentions of the trial

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.

Combs overdosed on opioids at the Playboy Mansion.

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.

Ventura said that Combs paid her $20 million to settle her lawsuit.

Cassie Ventura and Sean Combs — Cassie Ventura and Sean “Diddy” Combs in 2018.

Jeff Kravitz/FilmMagic

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.

Combs was said to be enraged over Ventura’s romance with Kid Cudi.

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.”

Prosecutors said Combs beat Ventura over bathroom use.

Sean Diddy Combs and Cassie Ventura — Combs and Ventura had an on-and-off relationship for 11 years.

Gilbert Flores/Variety via Getty Images; Johnny Nunez/WireImage

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 said she first joined Diddy’s freak offs out of love

Cassie Ventura poses in a brown corset top and floor-length black skirt. — Ventura is the prosecution’s key witness in the criminal trial of Sean “Diddy” Combs.

Emma McIntyre/Getty Images

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.”

Ventura said that the baby oil and lube used during freak offs would get everywhere.

Media members work as law enforcement officers stand behind police tape outside a property connected to hip-hop star Sean "Diddy" Combs. — US Department of Homeland Security agents raided Combs’ home in the Holmby Hills neighborhood of Los Angeles in March 2024.

REUTERS/Carlin Stiehl

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.

Source link