The first week of Sean "Diddy" Combs’ highly publicized criminal trial for sex trafficking and racketeering conspiracy commenced with shocking testimonies from Casandra "Cassie" Ventura. Ventura provided graphic and explicit accounts of the “humiliating” experiences she alleges she endured during her decade-long relationship with Combs. These sexual encounters are pivotal to the criminal charges against the music mogul, who is facing serious allegations.
Over more than 20 hours, Ventura detailed to prosecutors from the Southern District of New York and Combs’ legal team the explicit nature of the “freak-offs” that she claims started early in her relationship with the R&B star. “He introduced the concept when I was just 22, and I would do absolutely anything for him. It never stopped, and it was expected of me, which made me feel terrible about myself,” Ventura stated in court.
In stark contrast, Combs’ defense painted Ventura as a willing participant in their unconventional sex life. They presented various messages in which Ventura expressed her eagerness for the prolonged sexual encounters, with one message from September 2012 reading, “I don’t want to freak off for a last time; I want it to be the first time for the rest of our lives.”
Throughout the trial, Combs remained engaged in his legal strategy, taking notes and communicating with his attorneys. He maintained a stoic demeanor during much of Ventura’s testimony but visibly reacted when male escort Daniel Phillip testified about witnessing Combs allegedly throw a liquor bottle in Ventura's direction and drag her by her hair during an encounter.
As the week progressed, Combs’ three teenage daughters briefly exited the courtroom during Phillip’s graphic testimony, illustrating the personal turmoil surrounding this high-profile case.
If convicted on five federal charges, Combs faces a severe sentence of 15 years to life in prison. He has pleaded not guilty and has actively sought a speedy trial, even rejecting a plea deal. Reports indicate that Combs' allies are exploring the possibility of a presidential pardon should he be convicted.
The trial has drawn significant public interest, with over 100 attendees, including members of the press, legal professionals, and fans wearing “Free Diddy” T-shirts. Content creators and podcasters, such as Stephanie Soo from Rotten Mango and Myron Gaines from Fresh and Fit, have also been in attendance, highlighting the trial's extensive media coverage.
Ventura, the government’s key witness, took the stand confidently, recounting her experiences that she claims turned her into a “sex worker.” The “freak-offs” are central to the charges against Combs, with prosecutors alleging that he coerced Ventura into having sex with hired male escorts through manipulation and intimidation. Over four days, Ventura became emotional only twice while discussing the pain stemming from these experiences.
“I’d give that money back if it meant I never had to have freak-offs,” she tearfully stated about her $20 million settlement with Combs, underscoring the emotional toll these incidents took on her.
Ventura described entering a relationship with Combs as a “naive” and inexperienced 21-year-old shortly after signing with his record label, Bad Boy Records. She alleged that her promising music career was overshadowed by the demands of preparing for and recovering from drug-fueled sexual escapades. Combs allegedly controlled every aspect of these encounters, including her appearance and the drugs consumed beforehand.
According to Ventura, the sexual encounters often began with Combs applying baby oil to her body and would continue until he decided they were over. She testified that she was paid thousands of dollars in cash for the services rendered during these encounters, which Combs provided.
As part of her cooperation with prosecutors, Ventura provided several electronic devices containing thousands of communications between her and Combs. During cross-examination, defense attorney Anna Estevao highlighted explicit messages where Ventura seemed enthusiastic about participating in the freak-offs. “I’m always ready to freak off,” Ventura wrote in one message from August 2009. However, at times, she also expressed discomfort about the nature of their relationship, worried that it was limited to fulfilling his fantasies.
During her testimony, Ventura mentioned at least a dozen male escorts who participated in the sexual encounters, identifying one individual, Jonathan Oddi, who was reportedly involved in a previous scandal. Oddi's criminal history and outrageous claims about being Combs and Ventura’s “sex slave” were raised during the trial, adding further intrigue to the proceedings.
Following Combs’ arrest last September, agents discovered numerous bottles of baby oil and lubricant in his hotel room, along with a significant amount of cash. Special agent Yasin Binda testified about finding drugs, including ketamine and MDMA, further complicating Combs’ legal challenges.
As the trial continues, several key witnesses are expected to testify, including Ventura’s mother and her long-time friend, Kerry Morgan, who has been mentioned multiple times in the context of the allegations. With the trial projected to last several more weeks, public interest remains high as the courtroom drama unfolds.
