The trial of Sean “Diddy” Combs continued Tuesday in Manhattan federal court, with more witnesses — including his former personal assistant, a male escort who went by the name “the Punisher,” and Regina Ventura, the mother of his former girlfriend Cassie Ventura — testifying against him in the sex trafficking case.
Federal prosecutors say that for decades, Combs abused, threatened and coerced women to participate in marathon sexual encounters called “freak offs” and used his business empire, along with guns, kidnapping and arson, to conceal his crimes. The 55-year-old hip-hop mogul has been charged with sex trafficking, racketeering conspiracy and transportation to engage in prostitution.
Combs has pleaded not guilty. If convicted, he could face life in prison.
Here are some key takeaways from Tuesday’s testimony culled from various reporters and news organizations in the courtroom, including CNN, NBC News and the Washington Post.
Former assistant recalls stocking hotel rooms with drugs and baby oil
Combs watches as his former personal assistant David James is questioned by prosecutor Christy Slavik before Judge Arun Subramanian at his sex trafficking trial in New York City on Tuesday. (Jane Rosenberg/Reuters)
David James, an assistant for Combs from 2007 to 2009, returned to the witness stand for a second day of testimony. James told the court that he would stock hotel rooms with items for Combs before his arrival. They included a Louis Vuitton bag containing 25 to 30 pill bottles, drugs such as ecstasy and Percocet, baby oil, lubricant, condoms and $10,000 in cash.
For some supplies, like skin care products, James was reimbursed by Bad Boy Entertainment. But for others, such as baby oil and condoms, he was reimbursed by Combs’s security staff, who would pay him in cash out of the Louis Vuitton bag. He said a drug dealer nicknamed “One Stop” would often bring drugs to Combs, but Combs would occasionally ask James to procure drugs for him and his friends.
James told the court about a violent incident involving Combs and his personal chef, Jourdan Atkinson, at Combs’s Alpine, N.J., home. James said that Combs instructed him to file a police report falsely claiming that Atkinson was the aggressor and hit Combs first. But James said he did not want to file a false police report, so he drove around and returned to Combs’s home, where he lied and told his boss that the report had been filed.
James testified that on at least two occasions he was ordered by Combs to take lie detector tests administered by a former FBI agent after Combs’s jewelry went missing.
Combs had three handguns in his lap while looking for ‘Suge’ Knight, former assistant says
David James, Sean “Diddy” Combs’s former personal assistant, arrives at federal court in New York City on Tuesday. (Charly Triballeau/AFP via Getty Images)
James also testified about an incident in which he was ordered to drive Combs and a security guard at 4 a.m. to Mel’s Diner in Los Angeles looking to confront rival record producer Marion “Suge” Knight, who had been spotted there. Combs was in the back seat with three handguns in his lap, James said. Knight was gone by the time they got to the restaurant.
The incident prompted James to give notice that he planned to quit.
“I was really shook up by it,” James said. “This was the first time as his assistant that I realized my life was in danger.”
Under cross-examination by the defense, James was asked whether he considered his travel with Combs business or personal. James said there was a “fine line” between the two because Combs’s personal life and business life were so intertwined. In his testimony Tuesday, James said that before he was hired, an executive at Bad Boy Entertainment told him, “This is Mr. Combs’s kingdom, and we are all here to serve in it.”
Big picture: Prosecutors hoped to use James’s testimony to establish the racketeering charge — showing that Combs used his business empire to facilitate his alleged crimes.
Regina Ventura, Cassie’s mother, takes the stand
Regina Ventura, mother of Cassie Ventura, arrives at federal court to testify in Sean “Diddy” Combs’s sex trafficking trial on Tuesday. (Charly Triballeau/AFP via Getty Images)
Cassie Ventura’s mother, Regina Ventura, testified about what she witnessed during her daughter’s relationship of over a decade with Combs.
Under direct questioning from prosecutors, Regina Ventura recounted an email Cassie sent to her mother in December 2011 saying that Combs was threatening to release an explicit video of her after he learned she was dating Kid Cudi.
“I was physically sick,” Regina Ventura said. “I did not understand it; the sex tape threw me. He was trying to hurt my daughter.”
Around the same time, Regina Ventura said Combs contacted her saying he wanted to recoup $20,000 he had spent on Cassie. Regina Ventura said she was scared for her daughter’s safety and that the family took out a home equity loan to pay Combs the $20,000 he said they owed her. She said the money was wired back to her without explanation several days later.
Regina Ventura testified that the same month, Cassie showed her bruises from an alleged beating she took from Combs. Regina took photos of her bruised daughter, which were shown in court.
“She was bruised, and I wanted to make sure we memorialize it,” Ventura said.
The defense did not cross-examine Regina Ventura, and she was dismissed.
Big picture: Last week, Cassie Ventura spent four days on the witness stand, describing to the court in harrowing detail the physical abuse she says she suffered during her relationship with Combs. Regina Ventura spent less than an hour on the stand, corroborating some key parts of Cassie’s testimony but contributing little if any new information.
Male escort known as ‘the Punisher’ recalls his sexual encounters with Cassie Ventura and Combs
Sharay Hayes, a former erotic dancer, testifies at Sean “Diddy” Combs’s sex trafficking trial in New York City Tuesday in this courtroom sketch. (Jane Rosenberg/Reuters)
Sharay Hayes, a former male exotic dancer whose stage name was “the Punisher,” testified about his encounters with Cassie Ventura and Combs, including the first at Trump International Hotel in New York City. Hayes said that when he arrived at their suite, Ventura told him that she didn’t want him to dance but instead wanted him to help her create a “sexy scene” involving baby oil for her “husband,” who would be in the room. Hayes said Ventura told him not to acknowledge her “husband,” who entered with a veil he later realized was Combs.
“Ironically, I am a fan and follow him on Instagram,” Hayes said about Combs.
He said he was paid a total of $2,000 in cash for that encounter and was hired by the couple for a total of eight to 12 similar interactions, which always started with the application of baby oil and often ended with him having sex with Ventura. The sessions usually began around 2 a.m. or 3 a.m. Some, he said, lasted multiple days. Hayes said that Combs would sometimes direct Ventura to adjust the lighting or reposition her body.
Hayes said he felt increasing pressure while having sex with Ventura in front of Combs, eventually failed to perform and was never called back. He later wrote a self-help book about erectile dysfunction called In Search of Freezer Meat. It included a section on his experiences with Ventura and Combs, who he did not name, referring to them only as a married, wealthy couple.
Under cross-examination by the defense, Hayes said that he never sensed Ventura was uncomfortable, and never witnessed violence. “It seemed like it was consensual as far as I was concerned,” Hayes said.
Big picture: On the first day of the trial, a different male escort described a similar dynamic during his own sexual encounters with the couple. Prosecutors want to show the jury that there were witnesses to the control they say Combs had over Ventura to participate in the “freak offs” — including the male escorts they paid to join them.
Federal agent details raid on Combs’s Miami home
Homeland Security agents at the entrance of Sean “Diddy” Combs’s home in Miami Beach in March 2024. (Giorgio Viera/AFP via Getty Images)
Gerard Gannon, a federal agent who oversaw the 2024 raid on Combs’s Miami home, also testified on Tuesday.
Gannon said that between 80 and 90 law enforcement agents participated in the search of the 20,000-square-foot-residence on Star Island, an 86.5-acre island that is accessible by a single bridge. Some agents were positioned on boats to potentially intercept anyone trying to leave via the direct water access on Combs’s property, Gannon said.
The special agent told the court that a special response team was prepared to potentially confront Combs’s armed bodyguards. And a vehicle was used to break through the front gate, which Gannon said was “standard practice.”
Gannon said the search was intentionally executed after Combs had left for a scheduled trip with his family.
“We thought it was best to wait until him and his family left,” he said.
During the search, agents found lingerie, high heels, baby oil, personal lubricant and parts of AR-15 rifles in Combs’s closet. The serial numbers had been scratched off of the firearms, the special agent said.
Big picture: By having the special agent testify about the security measures surrounding the raid on one of his properties, prosecutors appear to be highlighting the seriousness of the charges Combs is facing.
