The Biggest Bombshells From Sean ‘Diddy’ Combs’ Trial, So Far

Since the start of Sean ‘Diddy’ Combs‘ federal trial on 5 May, the details coming out of the Manhattan courtroom have been nothing but grim, shocking, and disturbing. 

The first week of the trial saw Cassie Ventura as one of the key witnesses who testified while eight months pregnant. Her harrowing testimony revealed graphic details about her 11-year relationship with Combs, from the egregious ‘freak offs’ (a term Combs used to describe his orgies) to the emotional and physical abuse she endured at the hands of the rapper. 

The 55-year-old disgraced hip-hop mogul is currently facing federal charges of sex trafficking, racketeering, and transportation to engage in prostitution, and is expected to serve a life imprisonment should he be found guilty. 

Arrested in September 2024, the highly-awaited trial—which is expected to last eight to 10 weeks—comes after months of lawsuits and public accusations of sexual assault against the rapper. Combs and his defence team are pleading not guilty, arguing that all sexual activity was consensual and that his accusers have a financial motive in implicating him.

Since the trial has started, celebrities such as Cassie Ventura, rapper Kid Cudi, and singer Dawn Richard have taken the stand. Other A-list name drops in the court include former US President Barack Obama, Michael B. Jordan, Britney Spears, Usher, Kanye West, and Jennifer Lopez. 

Ahead, find out all the biggest bombshells from Combs’ ongoing federal trial. This article will continue to be updated.

[Warning: graphic descriptions of sexual assault, physical abuse, and drug use. Readers may find the details disturbing and distressing.]

Organising ‘freak offs’ became Ventura’s “job”

Ventura first met Combs when his label, Bay Boy Records, signed a record deal with her. She was 19 while the rapper was 36. According to Ventura, the relationship turned sexual when Combs kissed her on her 21st birthday and introduced her to his ‘freak offs’.

“He described it as a fantasy he had where he would want to see me having sexual interactions with another male so he could watch,” she revealed. “I just remember my stomach falling to my butt…I was confused, nervous, but I loved him so much.” Male escorts who testified, such as The Punisher (Sharay Hayes) and Daniel Phillip, also stated that Combs directed the scenes and watched, sometimes even wearing a head cloth similar to a niqab, while masturbating.

In Ventura’s words, the ‘freak offs’ would happen so frequently that organising them became her main responsibility over her music. “Freak offs 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,” prosecutor Johnson said.

“The ‘freak offs’ became a job where there was no space to do anything else but to recover and just try to feel normal again,” Ventura testified, noting that she and Combs would often be put on IV drips to recuperate from the long sessions.

She revealed she was directed to find male escorts on Craigslist or Backpage, and through a service called Cowboys 4 Angels. She would also be responsible for the logistics and for paying the escorts.

Ventura was urinated on and contracted multiple UTIs from ‘freak offs’

During the trial, Ventura went into graphic detail about what she was forced to do during the sex marathons. The 38-year-old recounted a time when Combs had directed the male escort to urinate together into Ventura’s mouth at the same time.

When asked if she wanted that to happen, Venture quickly responded, “No, I did not want it. I just felt humiliated. It was disgusting. It was too much. I choked. No one could think I wanted it.”

Ventura also further revealed that the orgies would happen so frequently that she suffered from numerous UTIs. “Sometimes they were back to back. I was actually doing the ‘freak offs’ with the infection.” The pain was excruciating and got to a point where antibiotics no longer worked. “Occassionally, I would get sores on my tongue from the ‘freak offs’, [from] taking drugs, substances, friction in my mouth,” she told the court. 

In her testimony, she states that even during her menstrual cycle, Combs still expected her to perform in the ‘freak offs’, and blood often stained the linens along with other bodily fluids, baby oil, and candles. As a result, the former singer stated that ‘freak offs’ would be “super pungent”.

According to Ventura, Combs would often film her during these sessions without her consent and use them as blackmail to coerce her into participating in more ‘freak offs’. 

Cassie was also physically abused by Diddy 

Apart from the sexual abuse that Ventura endured, she was also the subject of extensive physical abuse, as her testimony revealed. In her opening statement, prosecutor Emily Johnson told jurors that Combs used “lies, drugs, threats, and violence to force and coerce” Ventura to perform sexual acts. Any resistance “could and often would end in violence.”

“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 continued.

On 14 May, Ventura corroborated that by testifying about six separate times that Combs’ attack left her with visible injuries. One of them included an incident in 2009 when Combs severely beat Ventura for talking to a record producer. He called her a “slut or a bitch” in the car before continuing to kick and punch Ventura during the 10-minute ride back to the rapper’s mansion. 

“I was trying to cover my face,” Ventura testified. “Because Sean was stomping on it with his foot.” The beating left her with “black eyes” and “golf-ball-sized knots” on her forehead.

After the assaults, Combs’ team would set her up in hotels or keep her at home until her wounds and bruises healed. Ventura went on to testify that many people, including Combs’ security personnel, personal assistants, and drivers, witnessed the abuse but never intervened.

Ventura said “control was everything” in their relationship 

Another harrowing detail was when Ventura explained that Combs would control every aspect of her life, from her appearance to having her laptop and phone confiscated as “punishment”. 

She explained that Combs was obsessed with how she looked, and demanded that her nails only be painted white or as French tips, that she could only wear high heels, and that she comb her hair a specific way for the sex marathons.

“If I wasn’t doing my nails, I was getting a tan. If I wasn’t getting a tan, I was getting something else. The physical prep was for the ‘freak offs’—I had to look a certain way during ‘freak offs’.”

Ventura’s former best friend, Kerry Morgan, also testified to Combs’ controlling nature. “He controlled everything. She would’ve lost all of her livelihood,” she said, detailing that Combs paid for Ventura’s apartment and car, and had her under a 10-album contract.

Combs’ obsession with baby oil knows no bounds

While the details of sexual assault and physical abuse are enough to get anyone’s attention, Diddy’s apparent obsession with baby oil continues to be the topic of discussions. In March 2024, the Department of Homeland Security found “more than 1,000 bottles of baby oil and lubricant” during their raid of Combs’ Los Angeles and Miami homes. 

During her testimony, Ventura shared details about the use of baby oil and why they needed exorbitant amounts of it. “We poured it all over our bodies, they had to be glistening,” she explained. “It was always heated…we’d put it in the sink with hot water and it’d be heated up.”

Ventura also told jurors that Combs would constantly 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.” 

She went on to describe an incident in which Combs ordered her to get inside an inflatable pool filled with baby oil. “We used 10 bottles of baby oil, regular-size.” The extensive use of the body oils would often result in tens of thousands in property damage. “There was oil all over the walls, the door handles, the bed, the sheets.” 

Combs’ team paid $100,000 to bury the infamous hotel video 

One of the most damning piece of evidence from the prosecution is a 2016 video of Combs beating Ventura and grabbing her by the hair in the hallway of the InterContinetal Hotel in Los Angeles. The physical assault was caught on surveillance cameras and published in May 2024 by CNN.

The video was played to jurors, where Combs can be seen running after Ventura in a towel, before throwing her down and kicking her twice. He then dragged her body across the floor back to their room. According to prosecutors, the assault came after a ‘freak off’ session, and Ventura was looking to escape Combs while he was in the shower.

The hotel’s security guard, Israel Florez, was called to check in and testified to seeing a woman crouched in a corner with a broken vase on the floor, not recognising that it was Ventura at the time. According to prosecutor Johnson, Combs paid Florez $100,000 in a brown paper envelope in exchange for the footage. His bodyguards and chief of staff went to great lengths to obtain “what they thought was the only copy of that video.”

“I started to leave and [Combs] called for me,” Florez said. “He had a sack of money and he threw it at me and said, ‘Don’t tell anyone.'”

Kid Cudi calls Diddy a “Marvel supervillain”

Other than Ventura, the highest-profile witness to testify was rapper Kid Cudi, who briefly dated Ventura in 2011. He has been closely linked to Combs’ case since Ventura revealed in her 2023 lawsuit that the hip-hop mogul blew up Cudi’s car after finding out they were dating.

On the witness stand, Cudi told jurors that he believed Combs broke into his Los Angeles house. He found that his security cameras were not working, several brand packages were open, and his dog was locked in the bathroom and behaved very skittishly when Cudi got home. 

Cudi also believed that Combs torched his Porsche with a Molotov cocktail. “It looks like the top of my Porsche was cut open, and that’s where the Molotov cocktail was put in.”

After the break-in, the two rappers met up to talk things out. Cudi recalled Combs sitting by the window, looking out like “a Marvel supervillain.” During their conversation, Combs promised that he was not responsible for the car explosion, but Cudi affirmed in court that he believed Combs was lying.

Ventura and Combs settled for $20 million in her lawsuit 

On her second day of testimony, Ventura told jurors that Combs paid her $20 million to settle her civil lawsuit against him in 2023. She testified to suffering from “horrible flashbacks” and tearfully recalled one instance in March of that year when she attempted to “walk out the front door into traffic”. Her husband, Alex Fine, stopped her that night. 

Ventura then went to trauma therapy and rehab for drug addiction. She also began writing a book about her experiences and explained that she wanted Combs to read it and understand the pain he put her through. But the rapper didn’t take it seriously when it was sent to him, and she filed a lawsuit against him later on. 

“I wanted to be compensated for the time, the pain, the many, many years of trying to fix my life,” Ventura explained. When Combs’ defence lawyer, Anna Estevao, posed that the singer only cancelled her tour after she knew she was receiving the $20 million from Combs, Ventura denied it and said she would return the money if she could reverse Combs’ abuse.

At the end of her testimony, it was also revealed for the first time that Ventura would be receiving another settlement. The singer disclosed that she is expecting to receive approximately $10 million from InterContinental Hotels over the 2016 abuse incident that was captured on CCTV.

Cassie’s mother paid Diddy $20,000 as “recoup money”

On day seven of the trial, Regina Ventura testified that she paid Combs $20,000 when the rapper demanded the amount after finding out her daughter’s relationship with Cudi. Allegedly, he was upset because he had spent money on Ventura and now wanted compensation.

Ventura’s mother revealed that the former R&B singer had sent her an email explaining that Combs was threatening to “release 2 explicit sex tapes of me.” In it, she also told her mother that Combs would be “having someone hurt me” and “he has made a point that it wouldn’t be by his hands, he actually said he’d be out of the country when it happened.”

Mrs. Ventura testified that she took out a home equity loan to pay the amount and wired it to Combs, only to have the money returned to her days later. She also she took photos of her daughter’s injuries in 2011, which were shown to the jurors.

Dawn Richards says Combs threatened to kill her if she spoke out about the abuse 

Another celebrity who testified in court about Combs’ violence was singer Dawn Richard, a member of the group Danity Kane, which was formed on the music mogul’s show Making a Band 4.

Richard told the Manhattan court that Combs had threatened her with her life after she witnessed him punching, kicking, and taking a swing at Ventura with a skillet. According to Richard, Combs had said that if she told anyone of the attack, she “could go missing.”

The Danity Kane singer revealed that she witnessed Combs beat Ventura often. He “would punch her, choke her, drag her, slap her in the mouth. I saw him kick her, punch her in the stomach.”

Diddy’s former assistants were told to serve Combs’ “kingdom” 

Two former personal assistants were subpoenaed to testify in court and revealed startling information about what it was like to work with Combs. David James, who was the rapper’s PA from May 2007 to May 2008, described that they were meant to turn a blind eye to the violence they saw and not question anything.

“This is Mr. Combs’ kingdom,” the Head of HR allegedly told James during his interview, gesturing to a portrait of the rapper in his Manhattan headquarters. “We’re all here to serve it.”

James also recounted an incident that ultimately caused him to resign. The then-PA was ordered to drive to a diner where Combs learned that Suge Knight, Combs’ long-time hip-hop rival, was. Combs had three guns in his lap. At that point, James testified that he realised he might die that night from a shoot-out that was narrowly avoided.

Then there was George Kaplan, who worked 100-hour weeks for Combs from September 2014 to December 2015. He recalled an incident in 2015 when he heard Ventura screaming in the bedroom of Combs’ private jet.

Kaplan told jurors that he turned in his seat and saw the label founder standing over a crouched Ventura while holding a whisky glass. “Isn’t anybody seeing this?” he recounted Ventura crying out to the people in the jet, followed by sounds of crashing glassware and more screams.

Despite that, none of Combs’ security guards, assistants, and staff present intervened or checked on Ventura afterwards, he shared.

Cassie’s former best friend also testified to Combs’ violent outbursts

Ventura’s former best friend, Kerry Morgan, was called to the stand to testify about an alleged violent incident. She recounted Combs trying to smash his way into Ventura’s apartment with a hammer after the InterContinental Hotel incident, and described being terrified at his demeanour. He eventually left and no complaint was filed.

In another instance, during a vacation in Jamaica, Morgan testified to seeing Combs drag her best friend down a 50-yard hallway by her hair because she was “taking too long in the bathroom.”

But it wasn’t until an assault in 2018 that Morgan ultimately ended her 17-year friendship with Ventura. Morgan shared that Combs had choked her and attacked her with a wooden hanger, leaving her with a concussion. He had come to Ventura’s home, enraged that she was seeing someone else. 

Long-time former PA Capricorn Clark alleges she was kidnapped by Combs

On 27 May, Combs’ ex-assistant Capricorn Clark made an explosive testimony in the Manhattan federal court that may just tip the racketeering and kidnapping charges towards the prosecutor’s favour. Working for the rapper between 2004 and 2012, Clark is a key witness who has been closely linked to the case.

She testified that she was once held against her will for five days after several pieces of jewellery went missing. Combs had left her with his bodyguard, Paul Offord, also known as Uncle Paulie, who took her to a “dilapidated” run-down building to take a lie-detector test. 

Clark shared that she was brought into a room where a large man was present with a polygraph test. “If you fail this test, they’re gonna throw you in the East River,” the man told her. “I was petrified. I was afraid of what would happen if I didn’t pass this test.” She would be brought back to the building for the next five days to take the test repeatedly.

The former PA also told her side of the story about the Kid Cudi incident. She alleges that Comb came to her apartment with a gun and forced her into a car to go “kill” Kid Cudi. While they were breaking in, Clark secretly called Ventura on a burner phone and told her Combs was at Cudi’s house.

The Bad Boy Records founder then told Clark that he would not let her go unless Ventura came and promised that Cudi would not call law enforcement. “If you guys don’t convince him of that, I’ll kill all [of] you.”

When Ventura returned, Clark recalled seeing Combs attack her. “He kept kicking her, he never used his hand.” The ex-assistant was tearful during her testimony as she described how Combs pushed Ventura into the street, noting her fetal position as she shielded herself from his kicks. “She was crying silently, he was kicking her in the back.”

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