Wednesday, May 21, 2025
Jamie Wells
Jamie Wellshttps://themusicessentials.com/
Jamie Wells has a knack for getting the inside scoop on Hollywood’s biggest stars and up-and-coming talent. With a sharp eye for industry trends and an ear for viral moments, Jamie covers everything from red-carpet events to behind-the-scenes drama in movies, TV, and celebrity culture.

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Diddy Took Obama-Shaped Pills During Wild Parties Says Ex-Assistant

The courtroom chaos surrounding Sean “Diddy” Combs just got more bizarre.

On Tuesday, May 20, Diddy’s former personal assistant testified that the rapper regularly took ecstasy pills shaped like Barack Obama’s face. The shocking claim surfaced during the latest round of testimony in the music mogul’s ongoing federal trial in New York, where he faces serious charges including sex trafficking, racketeering conspiracy, and transportation to engage in prostitution. Diddy has denied all charges.

David James, who worked for Diddy from 2007 to 2009, dropped the wild allegation about the Obama-shaped drugs while detailing his former boss’s drug habits. “There were various pills, but one was in the form of a former president’s face,” he told the jury. “They were Obama-shaped ecstasy pills.” James explained that during the peak of Diddy’s career, he kept a Louis Vuitton pouch, basically a designer drug bag, on him at all times, filled with all kinds of pills.

James also backed up previous witnesses Cassie Ventura and Dawn Richard, who had both referred to the same toiletry bag as a “med bag.” According to James, the bag often contained Viagra, Percocet, weight loss pills, water pills, and even what he described as “sperm booster” pills. He claimed Diddy took drugs every single day.

In addition to his assistant duties, James said he occasionally joined in on the partying. He called the experience “Diddy-bopping”, his way of describing drinking Diddy’s own Ciroc vodka brand and taking ecstasy. James testified that his job wasn’t just about pills and partying, though; he was also tasked with stocking hotel rooms with Fiji water, Jello, applesauce, and, of course, plenty of Ciroc. The rooms were often booked under the name “Frank Black,” a pseudonym Diddy allegedly used for both hotel reservations and prescriptions.

But the testimony didn’t stop at pills and fake names. James told the court that Diddy kept a video of him dancing at a party, one that he found personally “embarrassing.” According to James, Diddy possibly held on to it to use against him someday “in case he ever needs it.”

Cassie Ventura, Diddy’s ex-girlfriend who was in a relationship with him for 10 years, had already testified that “Frank Black” was the name Diddy used during what he called “freak-offs”, drug-fueled sex marathons involving escorts and coercion. She claimed Diddy forced her to participate in these sessions weekly for years and that each one involved up to ten bottles of baby oil.

Things got even darker in the courtroom when jurors were shown photos of a hotel room that had been raided, which were made public on Monday, May 19, just as week two of the trial kicked off. Alongside those images, jurors were also presented with graphic photos of injuries Cassie claimed she received at Diddy’s hands.

This case has been nothing short of explosive, with every day bringing more disturbing allegations. From freak-offs and hidden identities to bizarre Obama-themed drugs, Diddy’s trial is becoming one of the most high-profile and surreal legal sagas the music world has ever seen.

Jamie Wells

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