Sean “Diddy” Combs allegedly overdosed on opioids while partying at the Playboy Mansion in 2012, shortly after the death of music legend Whitney Houston, his former girlfriend Cassie Ventura revealed Thursday.
Ventura was back on the stand Thursday as she faced cross-examination by Diddy’s lawyers. She has been testifying for days in the federal trial of the rap mogul. He faces accusations of sex trafficking and racketeering in what prosecutors say was an elaborate effort to fulfill his sexual desires. Diddy would achieve those goals by coercing or assaulting women or having them participate in “freak-offs” – sexual encounters he would sometimes film, prosecutors said.
His former girlfriend has spent days on the stand detailing how she participated in the freak-offs to keep him happy and be close to the star. She read text messages about them Thursday as she also spoke of the February 2012 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,” Ventura said. “From what he told me, he took a really strong opioid that night. But we didn’t know what happened, so we took him to the hospital.”
The new details about the overdose were just part of what Ventura discussed from the witness stand in a New York courtroom on Thursday. She also discussed:
- Explicit messages exchanged between her and Combs
- Defense attorneys argued that Ventura expressed excitement about engaging in freak-offs
- Ventura testified that Combs brought Britney Spears to her 21st birthday, where he first kissed her
- Combs and Ventura’s relationship was filled with volatility, often related to jealousy about their other romantic relationships
- Ventura said she began dating actor Michael B. Jordan around 2015 after finding out Combs had been spending time with another one of his girlfriends.

Despite defense attorneys cross-examining her, Ventura appeared more at ease on the stand Thursday. Wearing a button-down shirt under a black blazer with shiny lapels, she repeatedly pushed back on Diddy’s attorneys’ characterizations of the experiences in question. She never lost her temper or appeared annoyed, but at one point she pressed: “Can I speak?”
The jurors saw some of her charm. At another point, defense attorney Anna Estevao even told her she was ‘very beautiful and charming”, to which Ventura replied: “Thank you.” The room erupted in laughter. She later smiled and thanked Estevao after the attorney clarified she no longer had to read out loud the explicit messages she once sent her ex. At other times, she giggled because she saw old messages showing their age, including one text about her and Diddy going to see The Book of Mormon show.
Diddy, for his part, mostly leaned back in his chair throughout the day. He spoke to his attorneys during the lunch break and leaned forward occasionally to read exhibits.
Ventura, a star witness in the trial, told defense attorneys that she and Combs were dependent on opioids throughout their 11-year relationship. Diddy’s lawyer asked whether they were addicted to painkillers.
“Very much so,” Ventura replied.
At times throughout their relationship, Ventura would seek Combs’s attention by expressing interest in freak-offs. Ventura said she didn’t mean it when she expressed excitement.
“I would say that loving [freak-offs] were just words at that point,” Ventura testified.
She also told how she would shop for supplies for the freak-offs and was grilled about texts she sent with Diddy in 2017 near the end of their relationship. Ventura testified she went to an adult store and Diddy told her to “have fun, impress me” in picking out supplies.
The two exchanged text messages about her trying to avoid getting pregnant during a freak-off. In another message, she told Combs she forgot the iPad, which she previously said was used to record the encounters.

But it wasn’t just text messages about freak-offs they exchanged. The texts also showed jealousy between Combs and her, including her relationships with rapper Kid Cudi and movie star Michael B. Jordan.
Ventura was also jealous of Combs’s other romantic relationships. In one 2013 text message, she told Combs, “You’re making me look like a side piece and that is not what I thought I was.”
The defense attorney then asked Ventura if she was hurt that she didn’t appear to be Diddy’s main love interest.
“Yes,” she said. “It didn’t pertain to every situation, but I was definitely jealous of certain situations he was in.”
Estevao then asked if Diddy lost his temper and got jealous when she was in a relationship with Kid Cudi.
“A number of times,” Ventura told the court.