P. Diddy's former assistant reveals how he organized the rapper’s freak off parties in court testimony

P. Diddy trial: The rapper faces charges in New York including sex trafficking, racketeering, and human trafficking for prostitution purposes

After establishing coercion through Cassie's powerful testimony, the New York prosecutor overseeing the P. Diddy case moved onto the charges of human trafficking and transportation for prostitution.

The singer, who had signed a 10-album contract at age 19 after meeting Sean Combs in 2005—but has released only one album on his Bad Boy Records label since—detailed in court last week how she was subjected to "freak off" parties. Cassie described drugs provided by the rapper that allowed her to "dissociate" from her body during these orgies. She also mentioned the fear of violent reactions from P. Diddy, her intermittent partner of 11 years until 2018, if she ever refused to participate.

Professional management of orgies

Cassie mentioned that while P. Diddy asked her personally to contact male escorts, the organization of these “freak off” parties required much more than just a phone call to sex workers. The rapper’s team managed everything—from booking hotel rooms to purchasing lubricants, such as those found in large quantities by the FBI during two simultaneous raids—as George Kaplan testified this Wednesday.

The 34-year-old worked as an executive assistant for P. Diddy from September 2014 to December 2015, clocking between 80 to 100 hours per week, earning $125,000 annually according to USA Today. His responsibilities, as he explained in court, involved "protecting (P. Diddy) and his public image," as well as booking rooms under the fake name "Frank Black," a reference to "Frank White," the nickname used by Notorious B.I.G., who was signed to Bad Boy Records and killed in 1997.

Kaplan stated he made bookings in multiple cities across various U.S. states, including Los Angeles, Miami, and New York.

Workplace intimidation

According to Kaplan’s testimony, reported by The Independent, once a room was booked, he was required to transport bags and unpack their contents: "clothes, a speaker, candles, alcohol, baby oil, and Astroglide (a lubricant)." He also frequently purchased these items himself using a company credit card.

Kaplan, who is protected by an agreement with the FBI, further testified that Sean Combs called him to deliver drugs when the rapper was already inside hotel rooms, a task he performed without asking questions. He was also tasked with cleaning the hotel rooms after his employer left—not so much out of courtesy to the hotel staff, but to prevent employees from selling photos or videos to the media, thus "protecting Mr. Combs" from embarrassment.

George Kaplan added that P. Diddy threatened to fire him "almost monthly," sometimes presenting it as motivational and other times in a genuinely malicious manner. Another employee of P. Diddy, David James, testified about similar pressures. James was the rapper’s personal assistant in the late 2000s.

Similar methods of intimidation

James also described intimidation tactics at his workplace, including being subjected twice to lie-detector tests whenever money or a watch went missing. He was further suspected of leaking to the media photos showing Cassie with an injured eye in January 2009—images tied to an article claiming she had been assaulted by P. Diddy. The rapper reportedly demanded to inspect James’s computer history, as reported by The New York Times.

David James also described Louis Vuitton bags filled with cash and drugs that followed P. Diddy on every trip. Additionally, he recounted an incident in 2008 when he was forced to carry firearms to a restaurant in Los Angeles where Suge Knight—P. Diddy's rival who is currently incarcerated—was dining, according to TMZ. "It was the first time, as Mr. Combs’s assistant, that I feared for my life," James stated. He resigned six months later.