On Monday, June 16, jurors in the federal sex trafficking trial of Sean “Diddy” Combs were shown video footage for the first time—marking a significant turning point in the high-profile case. Until now, the courtroom had been dominated by audio recordings, still images, and hours of emotional testimony. But the introduction of graphic visual evidence brought the allegations into sharper focus.
The footage, which prosecutors say depicts drug-fueled group sex encounters known as “freak offs,” had been referenced repeatedly throughout the trial. Witnesses described how assistants booked hotel rooms, sourced oils and lubricants, coordinated with escorts, and handled large cash payments. The videos themselves, however, were played only for the jury and essential courtroom staff, who listened through headphones. Defense attorneys were excluded from viewing the clips on their screens, a rare procedural move that underscored the sensitivity of the content.
Testimony from Special Agent DeLeassa Penland accompanied the footage. She guided the jury through hotel receipts, flight logs, and text messages dating back to October 2012. At the center of those exchanges was Cassie Ventura, Diddy’s on-and-off partner between 2007 and 2018. According to Penland, Ventura used aliases—“Janet Clark” and “Frank Black”—to book hotel rooms for encounters involving male escorts. The location: Trump International Hotel in Manhattan.
Juror Removed as Texts Tie Diddy’s Team to Drugs and Party Culture
Earlier in the day, the court dismissed a juror for what Judge Valerie Caproni described as a “lack of candor.” The defense pressed for more clarity, concerned about the impact of the dismissal on the jury’s impartiality. An alternate has since taken that juror’s seat.
Prosecutors also presented a series of charts compiled by paralegal specialist Ananya Sankar, mapping out years of text messages related to the case. The communications, many involving Diddy’s chief-of-staff Kristina Khorram, suggested her awareness of both the events and the substances tied to them. One 2016 message referenced drugs stashed in a car trunk. Another, sent shortly before Ventura filed her lawsuit in November 2023, showed a participant pulling away from the lifestyle: “I’m not doing anymore hard partying…no more ‘hotel nights’ and all that stuff.”
Defense attorney Teny Geragos challenged the narrative, arguing the charts presented only a narrow slice of an eight-year timeline. “These are just select messages across eight years,” she told the court, urging jurors to consider context. In a separate revelation, prosecutors pointed to a February 2024 outreach Diddy made to a former assistant named Mia, who left his circle in 2017. While the government framed the contact as suspicious, the defense maintained it was simply an attempt to reconnect with someone from his past.
Diddy, who has pleaded not guilty, faces five federal charges, including sex trafficking, racketeering, and transportation for prostitution. With more witnesses expected—among them Brendan Paul, a former assistant accused of acting as a “drug mule”—the court continues to weigh whether the evidence supports the government’s sweeping allegations or reflects the blurred lines of a celebrity lifestyle.