The opening week of Sean “Diddy” Combs’ trial on sex-trafficking and racketeering charges centered on testimony from his former girlfriend, Casandra “Cassie” Ventura, who spent over 20 hours detailing explicit sexual encounters that prosecutors allege are central to the criminal case.
Ventura testified that Combs introduced her to “freak-offs” when she was 22, stating, “I would do absolutely anything for him, and I did. And it never stopped our whole relationship.” She explained these encounters involved hired male escorts and drug use, with Combs allegedly controlling every aspect from her appearance to the sex acts performed.
The defense portrayed Ventura as a willing participant, displaying messages where she appeared enthusiastic about these encounters. “I don’t want to freak off for a last time,” read one 2012 message, “I want it to be [the] first time for the rest of our lives.”
Combs actively participated in his defense, taking notes and passing information to his attorneys. While maintaining a neutral expression during most testimony, he noticeably scowled during testimony from male escort Daniel Phillip, who described seeing Combs drag Ventura by her hair. Phillip’s explicit testimony prompted Combs’ teenage daughters to briefly exit the courtroom.
If convicted of the five federal charges, Combs faces 15 years to life in prison. He has pleaded not guilty and rejected a plea deal in favor of a speedy trial.
Ventura described being introduced to “freak-offs” after signing to Combs’ Bad Boy Records as a “naive” 21-year-old. She testified that these drug-fueled sexual encounters hindered her music career and involved extensive preparation, including specific appearance requirements.
According to Ventura, sessions began with baby oil application until she was “glistening,” consuming up to 10 bottles nightly. She claimed she paid escorts thousands in cash provided by Combs and that the encounters only ended when he decided.
When questioned why she participated, Ventura cited fear of Combs’ anger and physical abuse, stating, “I worried for my safety; I worried for my career. But I also was in love with him.”
Defense attorney Anna Estevao presented numerous messages showing Ventura’s apparent willingness, including a 2009 text stating, “I’m always ready to freak off.” However, other messages revealed Ventura’s hesitation, with a 2009 email expressing that freak-offs made her feel “dirty and grimy.”
During testimony, Ventura identified multiple male escorts, including one identified as “Jonathan,” whom they stopped using after he secretly recorded an encounter. This confirmed allegations from Jonathan Oddi, who made headlines in 2018 after an incident at Trump’s Doral golf club,b where he claimed to be Combs and Ventura’s “sex slave.”
Another identified escort, “Ash,” matched the description of Ash Armand (Akshaya Kubiak) from Showtime’s “Gigolos,” who is currently serving 8-20 years for voluntary manslaughter.
Homeland Security special agent Yasin Binda testified about items found in Combs’ hotel room during his September arrest, including numerous bottles of baby oil and lubricant arranged in his bathtub, along with prescription Clonazepam under a pseudonym, ketamine, MDMA, and $9,000 in cash.
Former Danity Kane singer Dawn Richard also testified, describing a 2009 incident where she witnessed Combs allegedly beating Ventura over a food-related dispute, saying she had “never seen anything like it.”
Richard is expected to continue testimony when the trial resumes Monday, with Ventura’s mother and former best friend Kerry Morgan also scheduled to appear.
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