In the federal criminal trial of Sean “Diddy” Combs, prosecutors have begun stitching together an intricate web of evidence—personal communications, financial records, and explicit video footage—meant to support claims that the hip-hop mogul orchestrated a sex-trafficking operation. Tuesday’s proceedings added new depth to a case that has already captivated the public, with new material surfacing that deepens the questions surrounding Diddy’s inner circle.
Central to the courtroom’s focus was a resurfaced video from 2016 that allegedly shows Diddy assaulting his then-girlfriend, Cassie Ventura, in a hallway of a Los Angeles hotel. While jurors had previously seen the footage, Monday’s testimony brought attention to the communications that followed the incident. In a series of text messages exchanged between Diddy, Cassie, his chief of staff Kristina “KK” Khorram, and his longtime bodyguard D-Roc, the aftermath took shape. Diddy wrote Cassie, “about to be arrested,” urging her to return to the hotel. She declined, saying she would not come back and adding that the male escort involved in the night’s events had also left.
Jurors were also shown roughly 20 minutes of video footage that prosecutors say depicts a series of sex-fueled gatherings—known in the trial as “freak offs”—dating back to 2012 through 2014. These videos, prosecutors argue, are key to establishing a pattern of behavior at the center of the case. Brendan Paul, a former assistant to Diddy, is expected to testify on June 18.
According to filings, Paul is prepared to speak about his role in allegedly sourcing narcotics like GHB for these events. Though he was arrested last year for possession of cocaine and marijuana edibles, those charges were later dismissed. He now holds an immunity deal that protects him if his testimony remains truthful.
Defense Presses Consent Claims as Trial Tensions Mount
The defense has aimed to reframe Cassie’s role in the “freak offs” as consensual and even participatory. During cross-examination of Special Agent DeLeassa Penland, Diddy’s attorneys introduced text messages that suggest Ventura Fine helped coordinate escorts and logistics. One exchange from Diddy read, “You make the decision please.” Cassie later testified, “I would give that money back if I never had to have ‘freak offs,’” referencing her $20 million civil settlement.
Pressure in the courtroom increased when defense attorney Teny Geragos challenged the scope of the digital evidence. She questioned why Agent Penland had not requested full message threads rather than select excerpts. Penland responded that her job was to authenticate the submitted evidence, not to independently pursue additional texts.
Additional texts introduced in court highlighted the involvement of Diddy’s staff in the aftermath of the 2016 hotel assault. Khorram was seen coordinating with hotel security to obtain footage, while D-Roc downplayed the severity of Ventura Fine’s injuries in a message to Diddy. Financial records presented showed lavish spending tied to hotel stays and services surrounding these events.
Judge Arun Subramanian, overseeing the case, voiced concern over recent leaks of sealed material to the press. He demanded clarity from both legal teams about how the information may have reached tabloids, underscoring the importance of protecting the trial’s integrity. As the prosecution approaches its final days of testimony, the trial continues to raise complex questions around consent, power, and accountability within a high-profile circle. With both sides presenting sharply different narratives, the weight of the evidence and testimony will fall to the jury to interpret.