Diddy Trial: Evidence Reveals Disturbing Details of Alleged Hotel ‘Freak-Offs’ and Threats

The federal trial of music mogul Sean “Diddy” Combs took a deeper turn on Monday, June 16, as prosecutors presented damning digital evidence suggesting that the rapper orchestrated elaborate sex-fueled gatherings and attempted to cover them up.

On Day 24 of the racketeering and sex trafficking trial, the prosecution called Ananya Sankar, a paralegal specialist from the U.S. Attorney’s Office for the Southern District of New York, to testify about her work verifying messages, recordings, and travel logs linking Diddy and his aides to what they described as “freak-offs” — alleged drug-laced sex parties involving female escorts and male sex workers.

Among the evidence was a December 2019 text exchange between Diddy’s former assistant, Ryan Lopez, and ex-chief of staff Kristina Khorram. Lopez mentioned spotting “one of the cowboys” — believed to be a male escort — in the hotel lobby, to which Khorram replied with laughing emojis and asked, “how long is he going to stay awake?”

Further exchanges revealed how staff prepared for these events. In a January 2023 audio recording played in court, Khorram warned another former assistant, Dave Shirley, “Heads up, he’s about to do wild king tonight.” Shirley responded about collecting cash and restocking baby oil — an item repeatedly mentioned throughout the trial. Khorram also asked him to “bring up 15 bath towels.”

Prosecutors allege that these parties, described as “routine,” often left hotels damaged. Earlier testimony from a hotel manager noted rooms linked to Combs frequently required deep cleaning due to “spilled candle wax” and “excessive oil.”

Text messages presented in court also shed light on Diddy’s alleged control over women in his circle. In one December 2023 message, a woman testifying under the pseudonym “Jane” said Combs had threatened to leak explicit videos of her. “He said that he would expose me and send them to my child’s father,” the message read. This echoed earlier testimony from Regina Ventura, the mother of singer Cassie Ventura, who said Combs threatened her daughter with similar exposure.

The court also reviewed logistical texts regarding travel and frequent hotel damage fees tied to Jane’s stays. Prosecutors argue that these arrangements were part of a pattern of exploitation and coercion masked by Diddy’s lavish lifestyle.

In a procedural twist, Judge Arun Subramanian dismissed Juror Number 6 Monday morning after finding discrepancies in their declared residency. The juror was replaced by a 57-year-old Westchester County resident.

Sean Combs has consistently denied all allegations against him. His legal team maintains that the claims are unfounded and fueled by opportunism. The trial, drawing national attention due to its high-profile defendant and disturbing revelations, is expected to continue for several more weeks.

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