Diddy's Ex-Assistant Reveals Shocking Details in Court

 

The federal s3x trafficking and racketeering trial against Sean "Diddy" Combs continues to grip national attention, and this week, former executive assistant George Kaplan has offered a chilling alleged inside look into the mogul's private world. His testimony, which resumed Thursday morning (May 22, 2025) in New York City, has unveiled disturbing new claims about Diddy's alleged conduct.

Kaplan, who worked for Combs Enterprises between 2013 and 2015, painted a picture of duties far beyond a typical executive assistant. He testified to handling large sums of cash, including once carrying $50,000 aboard a private jet for Diddy and collecting $10,000 at a Western Union. While acknowledging Diddy's public relationships, Kaplan's testimony then delved into alleged behind-the-scenes violence.

Under questioning, Kaplan recounted a specific incident during a private flight to Las Vegas where he allegedly heard glass shatter during an altercation between Diddy and Cassie. Even more disturbing, he testified that Diddy later instructed him to procure creams using a corporate credit card to cover bruises on Cassie's face. Kaplan also claimed to have witnessed Diddy allegedly throw green apples "very hard" at Gina at his opulent Star Island mansion in Miami.

When pressed on why he didn't intervene, Kaplan's response was stark: "My career."

In earlier testimony on Wednesday, May 21st, Kaplan detailed how his responsibilities included booking hotel rooms under aliases in major cities, preparing them with items like baby oil and candles, and cleaning them afterward. He also claimed he was occasionally tasked with procuring food and drugs for Diddy.

Kaplan eventually left Combs Enterprises in 2015, citing moral concerns over "fixing those types of things," alongside his father’s health. Despite the disturbing alleged experiences, he stated he was grateful for the opportunity and held respect for Diddy, but ultimately felt compelled to resign.

As the trial enters its second week, Kaplan's testimony provides a stark, alleged peek behind the curtain of one of music's biggest figures, raising serious questions about the inner workings of his empire.