Diddy trial: Former assistant reveals rapper was taking pills shaped like former President Barack Obama

Shocking revelations have become a feature of the Sean Diddy Combs trial. The 55-year-old's trial on charges of sex trafficking and racketeering continued on Tuesday, May 20, 2025, in New York.

Diddy’s personal assistant, David James, who worked with the Bad Boy Records founder from 2007 to 2009, took the witness stand and discussed his two years of working with Combs. He revealed that he worked demanding hours and witnessed a lot of violence during his time working with Combs.

Part of his job was ensuring that Diddy’s hotel rooms were well stocked with items demanded by the rapper, which included fresh underwear, apple sauce, vodka, baby oil, viagra, an iPod, and condoms.

He also revealed that Combs had a pill bag that contained several drugs, including pills meant to look like the then-President of the United States, Barack Obama. He claimed that Combs was almost always on drugs every day, popping Percocet by day and ecstasy by night.

“There were various pills, but one was in the form of a former President’s face,” David James said on the witness stand, as reported by People.

When prosecutor Christy Slavik asked James which president he was referring to, James answered, “President Obama.”

More details on David James' testimony in Diddy’s trial

During his time on the witness stand, James also talked about the time he drove an armed Sean Combs to a LA dinner to allegedly confront Suge Knight. He testified that Combs sent him and a security guard named D-Roc to Mel’s Diner in Los Angeles to get some food, and upon getting there, they met Suge Knight, who he clarified was the rival of Sean Combs. He testified that four black SUVs pulled into the parking lot, and he allegedly saw someone pass Suge a gun.

“D-Roc said, 'We got to f***** go,” he said.

After returning to Diddy’s house, James testified that he had met his boss and Cassie, arguing outside.

Read more: "The more I heal, the more I can remember": Cassie issues statement as her Diddy testimony concludes

“Cassie looked very distressed. She was telling him not to go,” he told the Courtroom.

James revealed that Combs asked him to get into a black Escalade and drive to the dinner. He admitted that Combs was agitated and had three handguns on his lap.

“I was really struck by it. I realized for the first time, being Mr. Combs' assistant, that my life was in danger,” James said, claiming he handed in his notice and left the company a short while later.

Read more: Former aide claims Diddy "controlled" Cassie’s life and career in latest court testimony

Other witnesses who took the stand on the Tuesday trial include Cassie Ventura’s mother, Regina Ventura, who spoke about her daughter's abuse, and a male escort known as The Punisher, who testified about his alleged sexual encounters as part of Combs' parties.

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