Ex-Assistant Testifies To Diddy’s ‘Freak-Off’ Rituals In Hotel Room Setup
Written by djfrosty on May 22, 2025
Former executive assistant George Kaplan revealed unsettling details about his time working for Diddy at Combs Enterprises.
Kaplan, who served in the role from 2013 to 2015, told jurors that part of his duties involved preparing hotel rooms for Diddy’s private encounters, which he referred to as “freak-offs.” According to Kaplan, these preparations included setting up items like Astroglide lubricant, Johnson’s baby oil, and candles—creating an atmosphere tailored to Diddy’s specific preferences.
Kaplan testified that he regularly booked hotel rooms for Diddy in major cities such as New York, Miami, and Los Angeles. Among the locations mentioned was the InterContinental Hotel, where Diddy was later seen on surveillance footage assaulting singer Cassie in March 2016. Although Kaplan’s employment ended before that incident, his testimony painted a troubling picture of the behind-the-scenes operations at Combs Enterprises. He disclosed that he often reserved rooms under the alias “Frank Black,” a name inspired by The Notorious B.I.G.’s alter ego, Frank White.
Describing his job as grueling, Kaplan said he typically logged between 80 and 100 hours per week for a starting salary of $125,000. Despite the high compensation, he claimed the work came with intense pressure and verbal threats. “He told me he only wanted the best around him,” Kaplan said, alleging that Diddy would regularly threaten to fire him if he didn’t meet those expectations.
Kaplan’s responsibilities extended beyond logistics; he was also tasked with packing Diddy’s bags and then unpacking and arranging the room to meet his boss’s standards, often setting the mood with specific items in anticipation of private liaisons. Kaplan’s testimony is one of several key elements in a case that has drawn widespread attention for its explosive allegations.
His account adds to the growing portrait of a celebrity empire allegedly sustained by coercion, secrecy, and manipulation. As the trial continues, more witnesses are expected to shed light on Combs’ inner circle and the nature of his conduct. For now, Kaplan’s words provide a rare and intimate glimpse into the personal demands of one of the entertainment industry’s most powerful figures—and the troubling dynamics that may have enabled them.