Sean “Diddy” Combs Overdosed on Night of Playboy Mansion Party in 2012, His Ex-Partner Reveals at Trial

Sean “Diddy” Combs overdosed on painkillers the night he attended a Playboy Mansion party in 2012 as he battled addiction issues, which the beleaguered rap mogul and his former long-term girlfriend, Cassie Ventura, struggled with throughout their decade-long on-and-off relationship, she testified on Thursday at his federal sex trafficking and racketeering trial. 

The incident occurred around four years into their tumultuous relationship, which Ventura detailed as part of testimony she gave in a lower Manhattan federal court as the defense cross-examined her. Ventura has spent every day this week recounting for the court the lurid details of her time with Combs, which involved alleged physical abuse, manipulation, violence and her being coerced into participating in “freak-offs,” drug-fueled sexual encounters with male sex workers as Combs allegedly looked on and masturbated.

“Was that around the time Whitney Houston died? I believe so,” Ventura asked the defense lawyer when questioned about Combs’ overdose. “That evening we had a ‘freak-off.’ We went to a sex club in San Bernardino. And then he had a party at the Playboy Mansion that night, and I went home…From what [Combs] told me, he took a really strong opioid that night, but we didn’t know what happened. So, we took him to the hospital.”

Ventura told the defense attorney who questioned her about her time with the influential rap and fashion industry player that both she and Combs used painkillers and opioids throughout their relationship; at the time that Combs was at the top of the rap and fashion industries, he was an addict, Ventura testified. “I would say he was an addict,” she told the court, at a point also saying that “he needed to recover.” While being questioned by prosecutors earlier in the week, Ventura said that she began to take painkillers to numb herself after the punishing “freak-offs,” which could involve taking drugs and engaging in sex acts she says were orchestrated and directed by Combs for days on end. 

Combs was arrested in September and, in a five-count indictment, is accused by federal prosecutors of two decades of abuse of women, trafficking of sex workers and turning his music and fashion empire into a criminal enterprise. He has pleaded not guilty and denies all of the allegations against him. 

Ventura has a stint in a rehab facility in Arizona that she says didn’t stick and indicated that for both her and Combs, the addiction issues were intermittent and they would have conversations about wanting to clean up and stop using. The drug use impacted the “freak-offs,” Ventura revealed later on Thursday, saying that Combs expressed concern about getting caught in “the matrix,” which was their code for when they’d gotten too high for any sex to occur during a “freak-off.” 

The cross-examination of Ventura has largely consisted of the defense attempting to show her as a willing participant in the seemingly abusive relationship with Combs. Questions about her infidelity, drug use and her jealousy over his relationships with other women have been mostly deflected by Ventura, who is being forthright in testifying about aspects of her past that are less-than-flattering, clearly characterizing this as past behavior linked to a toxic relationship in her past. At one point, she told Combs’ defense attorney Anna Estevao that the reason she continued to participate in “freak-offs” with Combs was because to her it “was a job.” Ventura, who is now married and has two kids, is eight months pregnant as she details her time with Combs as the prosecution’s star witness.

Ventura’s 2011 affair with rapper Kid Cudi and romantic involvement with actor Michael B. Jordan was discussed in court, as she explained Combs’ “explosive” reaction when he learned of her infidelity or decision to date another celebrity. Infidelity was a frequent issue with the couple; Ventura testified that she was “jealous” of Combs’ relationship with his ex, late model Kim Porter, and said that after years of dating Combs, she wanted to be a part of his family life. Combs, she testified, would bring up the affair with Cudi throughout the relationship whenever his infidelity came up in arguments, she told the court. 

On Thursday the defense also presented the jury with a flurry of texts between Ventura and Combs, attempting to prove that she was a willing participant in the “freak-offs” and not coerced into doing anything against her will. 

In one message, Ventura wrote, “I am always ready to freak-off Lol.” Combs wrote in another, “I’m so horny,” and Ventura responded: “Omg I was just about to text you the same thing.” In a third, Combs texted, “I can’t wait” for one of their “freak-offs,” Ventura replied: “I can’t wait either.” One text message from Ventura the defense presented was so graphic that federal prosecutors objected and Judge Arun Subramanian sustained and called for a recess.

Ventura has testified that she participated in the drugs-and-sex marathons to keep Combs, her boss at Bad Boy Records and long-term romantic partner, happy and fulfilled. She told the court that at one point, she hoped to have a child with him.

With one day left of scheduled cross-examination, Judge Subramanian is urging the defense team to wrap up their questions. The defense argued that prosecutors called two witnesses this week ahead of Ventura’s testimony, and therefore, she should be available to them for completion of the cross-examination on Monday. 

“We will try to narrow it down,” said defense lawyer Marc Agnifilo. “This is a critical witness and I will come back in the morning and give you an estimate. It is an important witness and a very important case.”