Jurors in Sean “Diddy” Combs’ federal trial were confronted with disturbing and explicit footage on Monday (June 16), as prosecutors presented a series of short video clips allegedly recorded during the infamous “freak-off” sex sessions.
Per New York Times, the videos — sealed from the public but viewed privately by the jury using headphones and privacy-screened monitors — reportedly featured encounters involving Diddy and ex-girlfriend Casandra “Cassie” Ventura. Captured in 2012 and 2014, the clips were sourced from digital devices Ventura turned over to federal investigators amid her abuse claims against the Hip-Hop mogul.
In earlier testimony, Ventura described the “freak-offs” as coercive and emotionally scarring “sex marathons” that she agreed to under coercion. She detailed how Diddy would orchestrate the encounters, instructing her on what to do with male escorts while he watched, filmed, and/or pleasured himself nearby. She claimed these sessions weren’t just lived-out fantasies but tools of control as Diddy allegedly often recorded and weaponized the session with threats of exposure whenever she displeased him.
Cassie (L) Sean “Diddy” Combs attend the “Rei Kawakubo/Comme des Garcons: Art Of The In-Between” Costume Institute Gala at Metropolitan Museum of Art on May 1, 2017 in New York City.
Neilson Barnard/Getty Images
While the prosecution emphasized the non-consensual nature of these encounters, the defense team painted a different picture. They called the explicit footage “powerful evidence” of consensual sex between adults, arguing that no one involved was forced or trafficked. Diddy has also pleaded not guilty to all charges.
According to reports, several jurors appeared visibly stunned as they watched the footage, with some removing their headsets in discomfort. Perceived sex sounds were reportedly audible, bleeding through the headphones as the clips played. Prosecutors also shared a series of text and audio messages allegedly involving Diddy’s former chief of staff, Kristina Khorram, whom they describe as a key player in organizing the “freak-offs.”
Though she has yet to testify, Khorram has been cited as the 55-year-old’s “right hand” and a facilitator of his alleged sexual behavior.
Evidence of the latter was introduced in court through messages where Khorram allegedly arranged for Diddy’s luxury hotel suites to be stocked with items like baby oil, drugs, Gatorade, and even chicken noodle soup. In one 2016 exchange, she also allegedly directed an assistant to deliver $4,000 in cash to Diddy’s hotel, moving prosecutors to argue that there was a network that supported the alleged sexual exploitation taking place.
Diddy’s legal team, however, insists that “freak-offs” were not a criminal operation and that no witness will credibly claim to have been part of a racketeering enterprise. “There was not one,” she said of the alleged conspiracy, pushing back against what she calls “selective outrage and misinterpreted logistics.”
The father-of-seven was arrested in October 2024 at the Park Hyatt in Manhattan and remains in custody. If convicted, he faces a potential sentence of 15 years to life in prison.
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