Sean “Diddy” Combs’ federal sex trafficking trial took another dramatic turn this week as George Kaplan, the music mogul’s former executive assistant, delivered explosive testimony about his time working for the Bad Boy Records founder.

Kaplan, who was granted government immunity in exchange for his full cooperation, detailed a disturbing array of responsibilities he carried out while working closely with Combs. Among them, he said, was regularly booking hotel rooms for the artist’s so-called “freak offs”—a term allegedly used by Diddy to describe sexually charged private gatherings. The rooms were booked under the alias “Frank Black,” Kaplan testified, noting that Diddy’s preferred locations included the Trump International Hotel in New York’s Columbus Circle, the SLS Hotel in Miami’s South Beach, and the InterContinental in Los Angeles.

But Kaplan’s responsibilities didn’t stop at booking rooms. He also claimed he frequently cleaned up after Combs' stays to prevent hotel staff from selling compromising materials to tabloids or gossip outlets. “I knew hotels sometimes sold images or videos to embarrass celebrities, and I wanted to avoid that,” Kaplan said. He recounted one occasion in particular when he discovered “a brown crystalized powder” in a room. “I didn’t know what it was, and I got rid of it,” he added.

Kaplan also testified that he was regularly pressured to purchase drugs on Diddy’s behalf, and alleged that Combs would threaten his employment on a near-monthly basis. “There was always this underlying fear of losing my job,” he told the court.

Despite initially being enamored with the prestige of working for one of the most powerful figures in hip-hop, Kaplan said his loyalty began to crack after witnessing troubling incidents of alleged abuse. One such moment, he testified, occurred on a private jet when Combs became physically violent with singer Cassie Ventura, who has separately accused Diddy of years of abuse. Kaplan also recalled seeing Combs throw apples at another woman he was dating at the time, model Gina Huynh.

“I was not comfortable or aligned with the physical behavior that had been going on,” Kaplan stated, explaining his decision to ultimately walk away from his role.

Kaplan’s testimony adds to a growing list of former insiders and associates who have come forward to paint a troubling picture of Combs’ private life—allegations that he has vehemently denied through his legal team.

As the federal trial continues, the courtroom remains gripped by daily revelations, with more witnesses expected to testify in the coming weeks.

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