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The 11 biggest bombshells from the Diddy trial — including testimony by Kid Cudi and Cassie's mom

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  • 2025-05-23 04:19 event
  • 2 weeks ago schedule
The 11 biggest bombshells from the Diddy trial — including testimony by Kid Cudi and Cassie's mom
Sean Combs is on trial. From freak offs to a "death threat" described by Dawn Richard, here are the most striking revelations so far.

A courtroom sketch of Sean Combs among other people.
A courtroom sketch from September of Sean Combs and his attorneys.
  • It's the second week of testimony in Sean "Diddy" Combs' sex-trafficking and racketeering trial.
  • Cassie Ventura's mom and rapper Kid Cudi told jurors about times they physically confronted Combs.
  • Here are 10 of the biggest revelations from the trial so far.

It's week two of the Sean "Diddy" Combs sex-trafficking and racketeering trial.

A federal jury in Manhattan has heard R&B singer Cassie VenturaCombs' ex-girlfriend and the catalyst for his public downfalltearfully testify about the humiliating sexual violence she says she endured throughout their 11-year relationship.

Ventura's mother has described physically confronting Combs during a 2011 argument over her daughter's missing cellphone, and two male strippers have regaled the jury with sometimes X-rated testimony about "freak offs."

Along the way, there have been numerous celebrity mentions, including pop icon Britney Spears and actor Michael B. Jordan. Rapper Kid Cudi capped an already busy week two by describing his brief romance with Ventura, testifying that a jealous Combs broke into his LA home and unwrapped his family's Christmas presents.

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 about 10 months before the criminal charges, it accused Combs of rape, physical abuse, and controlling her during their relationship. The lawsuit was settled a day later for what Ventura testified was $20 million.

Combs has denied the charges. The music tycoon is arguing through his defense team that all sexual encounters were consensual, including the alleged drug-fueled freak offs. 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.

Kid Cudi said Combs broke into his house and probably torched his Porsche
A courtroom sketch of Kid Cudi, left, testifying at Sean "Diddy" Combs' criminal trial.
A courtroom sketch of Kid Cudi, left, testifying at Sean "Diddy" Combs' criminal trial.

Kid Cudi took the witness stand in Combs' trial on May 22, telling jurors that in December 2011, the music tycoon broke into his Hollywood Hills home, enraged after finding out about the rival rapper's short-lived romance with Ventura.

Kid Cudi, given name Scott Mescudi, told the jury that he returned home after the break-in to find the Christmas gifts he'd planned to give his family unwrapped and opened. His dog, he said, had been shut in the bathroom.

Mescudi said he was tipped off about the break-in in real time, when one of Combs' trusted assistants called him to say she was outside his house— and that Combs was inside.

"Motherfucker, you in my house?" Mescudi recalled telling Combs over the phone as he raced home to confront him.

Combs was gone by the time he arrived, Mescudi said.

Mescudi also told the jury that some two weeks later, his Porsche was firebombed while in his driveway.

Jurors had first heard about the firebombing when Ventura took the witness stand in the first week of the trial and described Combs' jealous rage on learning of her brief fling with Mescudi. She told jurors that Combs lunged at her with a corkscrew, threatened to release their sex tapes, and warned he'd torch Mescudi's car.

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."

The Porsche "arson" is a specific element in the racketeering charges against Combs. 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."

Cassie's mom describes 'trying to hit' Combs in a fight over her daughter's stolen phone
Regina Ventura, mother to star prosecution witness Cassie Ventura, arrives for her own testimony at the Manhattan sex-trafficking and racketeering trial of Sean "Diddy" Combs.
Regina Ventura, mother to star prosecution witness Cassie Ventura, arrives for her own testimony at the Manhattan sex-trafficking and racketeering trial of Sean "Diddy" Combs.

Regina Ventura corroborated her daughter's testimony, where she alleged two of Combs' violent, jealous rages over romantic rivals.

The first was from 2011. The mom said Cassie Ventura came home to Connecticut for the Christmas holidays that year with a large bruise on her back.

Cassie Ventura previously testified that the bruise was from being kicked to the ground by Combs after a fight over alleged romantic rival Mescudi.

The mom showed jurors a Blackberry text Cassie Ventura had sent while en route to Connecticut, memorializing what the daughter testified were Combs' threats to release sexually explicit videos, including on Christmas Day.

Combs also demanded that the family pay him $20,000 for "expenses," the mom testified. The family complied, taking out a second mortgage because "I was scared for my daughter's safety," she testified. Combs returned the money days later, the mom told jurors, giving no explanation for the refund.

Regina Ventura also told jurors about a 2016 incident that her daughter also testified about.

It was shortly before the younger Ventura's 30th birthday. Combs had swiped her cellphone, Cassie Ventura testified, after learning about her affair with an unnamed professional NFL player.

When she returned to her Los Angeles apartment without her phone, her mother, who was visiting, called the police and confronted Combs outside the building as her daughter remained upstairs, the elder Ventura testified.

"I was yelling and screaming and trying to hit him," the mom told jurors. "He did give it back," she told jurors of the missing phone.

Cassie screamed "Isn't anybody seeing this?" as Combs attacked her on his private jet, ex-assistant says
A courtroom sketch shows singer and key prosecution witness Cassie Ventura in tears on the witness stand at the Sean "Diddy" Combs sex-trafficking trial.
Singer and key prosecution witness Cassie Ventura was in tears on the witness stand at the Sean "Diddy" Combs sex-trafficking trial.

In some of the most compelling testimony of the trial, a former Combs personal assistant described watching — and doing nothing — as his boss brutally attacked a cowering Ventura in the bedroom of the rapper's private jet.

Former personal assistant George Kaplan, 34, said the attack happened on a crowded flight to Las Vegas in the latter half of 2015. Kaplan said he heard the sound of screams and shattering glass coming from the jet's bedroom.

He said he turned to see Combs standing over Ventura with a "whiskey rock glass" in his hand, as she cowered on the bed.

"After the glass crashed, Cassiie screamed, 'Isn't anybody seeing this?'" Kaplan told the jury.

"Did you look away?" asked a federal prosecutor, Assistant US Attorney Maurene Comey. Kaplan said he did.

"And after you looked away, what did you hear?" the prosecutor asked.

"Further glass crashing and chaos."

When the prosecutor asked what, if anything, the Combs security staff did in response, Kaplan answered, "Nothing."

No one, he said, went back to check on Ventura after Combs left the bedroom to rejoin his employees.

"I was 23 years old," Kaplan said in explanation of his own inaction. "All I wanted to do was have a great job in the entertainment industry."

Ultimately, he told the jury, this and similar domestic violence incidents drove him to quit.

Another former personal assistant told of the night he said Diddy went looking for Suge Knight
David james in a white shirt and blue jacket.
David James, a former assistant for Sean "Diddy" Combs.

Combs' former personal assistant spent two days on the witness stand, and in his most dramatic testimony, described how a 2008 run for cheeseburgers at an all-night diner nearly escalated the East Coast-West Coast rap wars.

It started at 4 a.m. in the parking lot at Mel's Drive-In in Los Angeles, the ex-assistant, David James, testified.

Combs' trusted security guard, Damian "D-Roc" Butler, noticed that Suge Knight, cofounder of rival recording studio Death Row Records, was sitting in an Escalade just a few parking spots away.

James, Combs' personal assistant from 2007 to 2009, testified that he was at the wheel of Combs' silver Lincoln Navigator when Knight and D-Roc faced off.

"What are you doing in my city?" James, according to his testimony, remembered hearing Knight asking Combs' security guard, who had introduced himself as "D-Roc, Biggie's boy," a reference to the rapper Notorious B.I.G.

Within moments, James and the bodyguard saw someone pass a gun to Knight and watched as four SUVs pulled up into different corners of the parking lot, he told jurors.

James testified that he was ordered by D-Roc to speed back to Combs' Hollywood Hills estate. There was no mention of whether they drove back with or without the cheeseburgers.

Once back home, and as Ventura protested in tears, Combs grabbed three guns for the ten-minute drive with D-Roc back to Mel's, testified James, who said he was still the driver.

Knight was nowhere to be found upon their return, James said.

"It was the first time I realized my life was in danger," the former PA testified, telling jurors that he sent in his resignation soon after.

Dawn Richard testified about a brutal beating, an alleged death threat, and flowers
Dawn Richard and Sean Combs.
Former Danity Kane member Dawn Richard testified against Sean "Diddy" Combs at his trial.

Danity Kane singer Dawn Richard was the fifth prosecution witness, and her testimony on May 16 alleged that in 2009, Combs brutally beat Ventura after she took too long to cook him dinner.

"Where's my fucking egg?" Richard recounted to the jury 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 testified. Then he dragged her upstairs by her hair, she said, adding that she then 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, she said.

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

She said Combs told the two women that "he was trying to take us to the top, and that, where he comes from, people go missing if they say things like that, like, if people talk. And then he gave us flowers."

While back on the stand on May 19, Richard re-emphasized that she felt this was a threat to her life.

The details in the testimony came as a surprise to Combs' 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.

On cross-examination on May 19, Richard agreed that she only recalled the alleged death threat in speaking with prosecutors earlier this month. It had gone unmentioned, she agreed, during a half-dozen prior interviews with prosecutors.

Combs attacked Ventura over bathroom use, prosecutor and ex-bestie say
Sean Diddy Combs and Cassie Ventura
Combs and Ventura had an on-and-off relationship for 11 years.

Ventura was beaten by Combs for the most minor of perceived infractions, including taking too long in the bathroom, prosecutor Emily Johnson said in her opening statement.

"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," Johnson said.

Ventura's ex-best friend, Kerry Morgan, was called to the witness stand on May 19 and told jurors about two attacks on Ventura she witnessed, including one while on vacation in Jamaica in 2013.

Morgan said Ventura at one point went to the bathroom at the residence where they were staying, and Combs said, "She's taking too long."

"A few minutes later, I heard her screaming — like guttural. Terrifying," Morgan said. "He was dragging her by her hair on the floor."

Morgan told jurors that she saw Combs push Ventura to the ground, causing her to hit her head on the paving bricks.

"She didn't move. She fell on her side," Morgan said, adding, "I thought she was knocked out."

Ventura, too, had testified that arguments with Combs would regularly result in physical abuse.

Ventura —who dated Combs on and off from 2007 to 2018 — described six separate times when 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.

She said she hid under the back seat to escape the attack. Combs demanded she stay hidden in a hotel for a week so her bruises could heal, she said.

The surprising things Combs kept in his luxury NYC hotel room while waiting to be arrested
Sean "Diddy" Combs.
Sean "Diddy" Combs was arrested in September 2024.

The prosecution's fourth witness took the witness stand briefly on May 16 to detail what she and other Homeland Security investigators say they found inside Combs' suite at Manhattan's 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.

Ventura's big settlements after her lawsuit and that infamous hallway-beatdown video
A court sketch depicts Sean "Diddy" Combs facing singer and ex-girlfriend Cassie Ventura, the star prosecution witness at his racketeering and sex-trafficking trial in Manhattan.
Cassie Ventura testified over the course of four days at Sean "Diddy" Combs' trial.

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 one of Combs' freak offs.

The jury was shown the infamous footage at the beginning of the trial.

Johnson, the prosecutor, said in her opening statements that at the time of the attack, Combs paid a security guard at the hotel $100,000 in a brown paper envelope in exchange for the footage.

Combs apologized for his actions in the video after CNN published the footage last year.

It was the second big-money settlement revealed in Ventura's testimony.

Earlier in her testimony, Ventura told jurors that Combs paid her $20 million to settle her civil suit against him in 2023.

Britney Spears and Michael B. Jordan became the biggest celebrity mentions of the trial
Britney Spears.
Britney Spears was among the celebrities mentioned at Sean "Diddy" Combs' 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 that Combs, 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 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.

Combs overdosed on opioids at the Playboy Mansion, Ventura said
playboy mansion
Sean Combs went to a party at the Playboy Mansion and got sick on painkillers, Cassie Ventura testified.

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, Combs' defense attorney, 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 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.

Ventura testified on May 13 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.

Johnson said in her opening statements that Combs eventually made it Ventura's job to find and book escorts to participate in the sex encounters.

While on the stand, Ventura described in detail what went on during freak offs. Prosecutors say Combs arranged, directed, and often electronically recorded the sex performances.

Ventura testified 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."

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