Former employee describes arranging hotels for Sean ‘Diddy’ Combs’ parties.

Testimony from George Kaplan in Diddy Trial

George Kaplan, who worked as an assistant for Sean “Diddy” Combs from 2013 to 2015, shared his experiences in court on Wednesday. He often found himself coordinating hotel stays where Combs engaged in, well, peculiar activities with other celebrities.

Initially, Kaplan’s duties revolved around fetching food and toiletries for the 55-year-old rapper. But as time went on, his responsibilities expanded because Combs began to trust him more.

During his testimony in Manhattan Federal Court, Kaplan recounted a specific incident where he had to deal with a bag containing Combs’ personal items. This bag included clothes, speakers, liquor, and other items, leading to a somewhat unique office arrangement for Combs.

He frequently had to book hotel rooms under the alias “Frank Black” in various cities, including New York, Los Angeles, and Miami. Some of Combs’ go-to hotels were the Trump Hotel in Columbus Circle, SLS in South Beach, and InterContinental in Los Angeles. In fact, Combs had previously expressed his disdain for the now-closed InterContinental Hotel in Century City due to its notorious reputation.

Last week, another witness, Ventura, spoke about her first encounter with these “freak-offs” at age 22, noting Combs may have viewed the situation as voyeurism—deriving pleasure from observing others engage in intimacy. She mentioned that these events occurred weekly, with some lasting several days.

At these gatherings, Ventura claimed that escorts would participate in sexual activities while coated in baby oil, as Combs watched nearby.

Kaplan insisted that he played a crucial role in preparing for these gatherings, assembling bags filled with baby oil, astroglide, and other items. He testified that after the events, his job involved cleaning up the hotel rooms and disposing of numerous liquor and baby oil bottles—necessary to maintain a low profile and avoid scrutiny from hotel staff.

He also noted that hotels often sell images or videos of high-profile guests, which he strived to prevent. Kaplan mentioned he even found a suspicious-looking brown powder but, unsure of its nature, decided to dispose of it.

Although primarily involved in organizing these “freak-offs” with his girlfriend Ventura, Kaplan also needed to pick up prescriptions for Combs. He highlighted that he could testify without fear of repercussions due to government-provided immunity.

Working as an executive assistant meant putting in significant hours—sometimes up to 100 a week—for which he earned $125,000 in his first year. Despite being viewed as a trusted ally, Kaplan noted that Combs would often remind him of the precarious nature of his position, implying that job security was never guaranteed.

The trial has seen Combs charged with serious offenses, including sex trafficking and using Combs Enterprises to facilitate illegal activities, all of which he denies.