‘He Took a Lot of Drugs’: Sean ‘Diddy’ Combs’s Ex-Girlfriend Says He Overdosed at the Playboy Mansion, Admits She Enjoyed ‘Freak-Off’ Sex Parties

The music producer, rapper and businessman Sean “Diddy” Combs, whose sex-trafficking trial is under way in Manhattan, was addicted to painkillers and overdosed, an ex-girlfriend who is a key witness, Cassandra Ventura, testified on Thursday under cross-examination by the defense. Her testimony will resume on Friday. “Do you remember when Mr. Combs overdosed in February 2012?” one of the defense attorneys, Anna Estevao, asked Ms. Ventura, who dated the defendant between 2007 and 2018. “That evening, we had a freak-off,” Ms. Ventura replied, referring to the drug-fueled sex sessions she and Mr. Combs would often engage in, hiring male prostitutes and using large amounts of baby oil. After one “freak-off,” which took place in California in February 2012, the couple, Ms. Ventura said, “went to a sex club in San Bernardino,” and then Mr. Combs “had a party at the Playboy Mansion that night,” which Ms. Ventura did not attend, saying she went home instead. “Did you learn what happened at the Playboy Mansion?” the defense attorney asked on Thursday. Attorney Marc Agnifilo arrives during Sean ‘Diddy’ Combs’ trial at Manhattan federal court on May 15, 2025. John Lamparski/Getty Images“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,” Ms. Ventura told the court. “And you assisted in taking him to the hospital?” Ms. Estevao asked. “Yes,” the witness said. “And you learned at the hospital that he had overdosed, right?” the defense pressed. “I believe so,” Ms. Ventura said. Cassie Ventura and Sean ‘Diddy’ Combs appear at the premiere of ‘Can’t Stop, Won’t Stop: A Bad Boy Story’ on June 21, 2017, in Beverly Hills, California. Chris Pizzello/Invision/AP, FileAfter two days of direct questioning from the prosecution, the defense finally got its chance to cross-examine Ms. Ventura on Thursday. Ms. Ventura is a key witness in the case against Mr. Combs, who is charged with racketeering conspiracy, sex trafficking, and transportation to engage in prostitution. He faces a maximum of life in prison if convicted. Mr. Combs has pleaded not guilty to all charges. In November 2023, Ms. Ventura filed a civil lawsuit against Mr. Combs, alleging years of physical and sexual abuse, and also that he raped her. That lawsuit was settled in less than a day, and according to her testimony she received $20 million. The accusations she made laid the groundwork for the criminal charges Mr. Combs now faces in federal court. Prosecutors, making use of criminal statutes designed to go after the mob, contend that Mr. Combs’s “freak-offs” were organized by members of his crime enterprise, which possessed illegal guns, purchased illegal drugs, kidnapped people, and illegally “trafficked” women and male prostitutes for sex. Mr. Combs’s defense says that he’s “a swinger” who was in a mutually violent relationship with Ms. Ventura, and that applying racketeering and sex trafficking laws to their lifestyle is preposterous.On Thursday, the defense directly asked Ms. Ventura if she understood that after her lawsuit was publicized in November 2023, Mr. Combs’s career was “ruined.” Before she could answer the question, the prosecution objected. But Mr. Combs’s empire — including a clothing line, partnerships with liquor companies and a cable network, and his record label — all took a steep fall after Ms. Ventura’s allegations against him became public. Quincy Brown and King Combs exit Manhattan federal court during the Sean ‘Diddy’ Combs’ trial on May 15, 2025. John Lamparski/Getty ImagesUnder questioning from the prosecution, Ms. Ventura had told the jury graphic details about “hundreds” of “freak offs” she participated in for years, as well as numerous incidents where Mr. Combs beat her, kicked her, and even stomped on her head. The jury also watched the now infamous video taken by surveillance cameras at the InterContinental hotel in Los Angeles in March 2016, which shows Mr. Combs running through the hallway in a towel, chasing after Ms. Ventura, who is attempting to leave, and violently hitting her head, pulling her to the ground, and trying to drag her back to the room. The defense was now trying to establish that Mr. Combs may have been experiencing opiate withdrawal symptoms on that day and also during other times, when he was violent. Ms. Estevao kept inquiring about Mr. Combs and Ms. Ventura’s frequent use of painkillers, asking if the witness would agree that the couple was “addicted to painkillers” for “almost the entire duration” of their relationship. “Very close to it, yeah,” Ms. Ventura agreed. This frame grab taken from hotel security camera video and aired by CNN appears to show Sean ‘Diddy’ Combs attacking singer Cassie in a Los Angeles hotel hallway in March 2016. CNN via AP, fileThe defense then steered the conversation to the withdrawal that Mr. Combs suffered when was off the painkillers, and how it would affect his mood and their relationship. Ms. Estevao asked if the withdrawal symptoms were “a big part of Mr. Combs’s mood swings.” “I don’t know if it was a big part, but it was a part,” Ms. Ventura replied. “You understood that if he did not get his painkillers that he was reliant on, that it would affect his mood, right?” Ms. Estevao pressed. “Yeah, anybody that’s addicted to painkillers is like that,” Ms. Ventura admitted.At another point, Ms. Estevao asked if Ms .Ventura remembered that Mr. Combs would get irritated when “he came off” the opioids. Ms. Ventura remembered, adding that “drugs don’t help you do anything. … There was a lot of drug use. He took a lot of drugs.” The drugs she listed, in addition to opioid painkillers, included ketamine (which was her preferred drug because it made her feel “disassociated”), ecstasy, MDMA, and cocaine.Janice Combs exits for lunch during Sean ‘Diddy’ Combs’s trial at Manhattan federal court on May 15, 2025. John Lamparski/Getty ImagesMr. Combs’s preferred drug was ecstasy, Ms. Ventura said, because it stimulates the senses and creates feelings of euphoria, while opioid painkillers “were a regular drug … a day drug.” The defense then asked if Ms. Ventura had been “very close” to Mr. Combs during their relationship, and possibly “understood” him and his mood swings better than other people. Ms. Ventura confirmed this.During the first part of the defense’s questioning, Ms. Ventura was asked about how she fell in love with Mr. Combs after her 21st birthday, and how they grew to be very close very quickly. The jury was also shown text messages and emails between her and Mr. Combs that were intended to portray her as a more than willing participant in the “freak offs,” to disprove the prosecution’s allegation that she was coerced into them. And Ms. Ventura confirmed not only that she booked the male escorts but also that she often enjoyed the “freak offs.” She also said that he had “that energy — that inspiring energy” that always drew her to him. Her testimony clashed with her description, during direct examination, of the freak-offs as degrading, coercive experiences that included male prostitutes urinating in her mouth under Mr. Combs’s instruction. Sean ‘Diddy’ Combs and Cassie attend the Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala at the Metropolitan Museum of Art on May 7, 2018. Neilson Barnard/Getty ImagesCiting text messages and emails, the defense showed that the two did in fact have an affectionate and loving relationship that was often plagued by jealousy, as the defense had already laid out during opening arguments. Ms. Ventura admitted that her feelings were hurt because she did not spend Christmas with Mr. Combs, who would spend the holidays with his children by other women. One year, on Father’s Day, she sent him a text message saying, “can’t wait until we have a baby of our own to celebrate father’s day. I love you with all my heart.” (Ms. Ventura and Mr. Combs never had children. She went on to marry her and Mr. Combs’s personal trainer, Alex Fine. They now have two children and she’s eight and a half months pregnant with their third.)But while Ms. Ventura was hurt, she confirmed, by other women Mr. Combs dated, she would also date other men. She testified that she had an affair with the actor Michael B. Jordan, now an “A-list Hollywood star,” and also with the rapper Kid Cudi, who acts under his birth name, Scott Mescudi. As the defense explained, Mr. Combs had introduced him to Ms. Ventura with the intention that she record a song with him. Prosecutors are expected to argue that Mr. Combs had Mr. Mescudi’s car firebombed in a fit of romantic jealousy.Combs makes a loving gesture to his family. Elizabeth Williams via APThe defense’s cross-examination will resume on Friday. The lead defense attorney, Marc Agnifilo, was unsure if the time would suffice to get through the many issues that need to be addressed. But the judge pressed him to get through with the questioning, because Ms. Ventura could possibly go into labor as soon as this weekend. The defense was not pleased with the pressure in a case involving a client who faces “a life sentence,” but the attorney said the defense would try to be done by end of day on Friday.

‘He Took a Lot of Drugs’: Sean ‘Diddy’ Combs’s Ex-Girlfriend Says He Overdosed at the Playboy Mansion, Admits She Enjoyed ‘Freak-Off’ Sex Parties

‘He Took a Lot of Drugs’: Sean ‘Diddy’ Combs’s Ex-Girlfriend Says He Overdosed at the Playboy Mansion, Admits She Enjoyed ‘Freak-Off’ Sex Parties

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