Diddy's Former Assistant, George Kaplan, Allegedly Cleaned up Hotel Rooms His Boss Used for Freak Offs

Running an empire requires a ton of help because there are undoubtedly a lot of moving parts. In the entertainment world, some might say these individuals are part of an entourage. A more cynical person might use the word "sycophants" when describing the hangers-on. When someone gets to the level where Sean "Diddy" Combs was at, it's hard to tell where the crew ends and the staff begins. As far as responsibilities go, sometimes a person is both.

After Diddy was arrested and charged with sex trafficking in September 2024, his once semi-secret world was slowly revealed. A seemingly endless number of lawsuits have been filed by victims alleging all manner of abuse. His circle of employees was scrutinized as the general public wondered just how much those closest to him really know. In May 2025, Diddy's trial began, and in week two, a man named George Kaplan testified. Who is he? Here's what we know.

In week one of Diddy's trial, his ex-girlfriend Cassie Ventura testified about their decade-long relationship. An already grueling recount of years of alleged abuse was made worse by the fact that Ventura is more than eight months pregnant. After she was done, Ventura's mother and former best friend took the stand. The following week, rapper Kid Cudi testified about his relationship with Ventura and alleged threats made against him.

The witness list is almost like a road map. Ventura spoke about the numerous Freak Offs she was allegedly forced to participate in while dating Diddy. They were held in various locations, which involved a fair amount of logistics. Insert George Kaplan, who testified in week two. The former aide to Diddy was an executive assistant at Combs' holding company, Combs Enterprises, from 2013 to 2015, and according to Kaplan, his job description was rather unorthodox.

He was initially hired to run errands for Combs, reported Page Six, such as shopping for household items and whatever else his boss may need. As Diddy learned to trust Kaplan more, his role changed over time. Kaplan was tasked with booking hotels for Diddy that were allegedly used for Freak Offs. He would then clean the rooms, which involved getting rid of bottles of baby oil and Gatorade. He once threw out some "crystallized powder on the counter of the bathroom sink," per People.

Kaplan was free to discuss everything he saw while working for Diddy, including drug use, because the former aide was given immunity in order to testify without fear of retribution. He was paid a $125,000 a year salary and worked 80 to 100 hours a week, per USA Today. Despite his dedication, Kaplan said Diddy constantly threatened to fire him.

Kaplan explained Diddy's erratic behavior by claiming it was because the music mogul only wanted to be "surrounded by the best." In order to keep his boss happy, Kaplan had to carry a kit with him at all times that allegedly contained Advil and ketamine for the rapper. The former assistant finally quit in 2015 after witnessing Combs allegedly getting violent with Ventura on a private plane.