High-profile names like Usher and former President Barack Obama were brought up during Monday’s testimony in the ongoing federal trial of music mogul Sean “Diddy” Combs, who is facing several felony charges related to sex trafficking, extortion, and racketeering. The case, now in its third week, continues to draw widespread attention due to the nature of the allegations and the number of celebrities involved or mentioned.
The courtroom heard from several of Combs’ former assistants, industry colleagues, and his ex-girlfriend, singer Cassie Ventura, as prosecutors worked to paint a clearer picture of the environment surrounding the music executive. The trial officially began with jury selection on March 5, and opening statements were made on May 12.
One of the key testimonies on May 20 came from Combs’ former assistant, David James. He claimed that Diddy often carried around “25 to 30” pill bottles, many of which allegedly contained ecstasy. When asked to describe the pills, James testified that one of them was shaped like the face of a former U.S. president. When pressed further, he identified the face as that of President Barack Obama.
In a separate incident, singer Dawn Richard, formerly of the group Danity Kane, testified about a violent altercation involving Combs and Ventura. According to Richard, the incident occurred during a private dinner in West Hollywood. Richard described a moment when Combs allegedly punched Ventura in the stomach during a quiet argument. Richard said Ventura bent over in pain and was then told to leave by Combs.
Richard said several individuals were present at that dinner, including Usher, music executive Harve Pierre, members of Diddy’s security team, and singer Kaleena Harper. During cross-examination, Richard was asked to clarify the guest list, and she added that Jimmy Iovine and Ne-Yo were also there, along with others she could not recall by name.
Testimony also continued regarding events tied to the so-called “freak off” parties. These gatherings are a central part of the prosecution’s case, with allegations that Combs forced attendees—often his employees or aspiring artists signed to his label—to engage in sex acts and use drugs. These claims have formed a major element of the trial.
Former President Barack Obama’s name came up during testimony in the federal trial against music mogul Sean “Diddy” Combs.
Diddy’s former personal assistant testified that A-list Diddy partygoers were taking pills shaped like Obama’s face. pic.twitter.com/rVCUyPCjkl
— arnaud robert (@arnaud_robert1) May 24, 2025
On May 22, rapper Kid Cudi took the stand to discuss a separate incident. Cudi testified that Combs once broke into his home after finding email communication between him and Ventura. A month later, Cudi said, his car was set on fire. He explained to the court that he reached out to Combs directly after the fire because he believed the music mogul was involved. However, when asked to elaborate on that belief, Diddy’s legal team objected, and Judge Arun Subramanian instructed the jury to disregard that part of the testimony.
REPORT: A former aide to Sean “Diddy” Combs just named Barack Obama in federal court, and Diddy’s legal team immediately tried to shut it down.
The media is talking about ecstasy pills shaped like Obama, but they’re leaving out the bombshell: Diddy allegedly met with Obama and… pic.twitter.com/XYCCzBKRaO
— The Vigilant Fox 🦊 (@VigilantFox) May 21, 2025
Sean Combs, now 55 years old, has pleaded not guilty to one count of racketeering conspiracy, two counts of sex trafficking, and two counts of transporting individuals for the purpose of prostitution. The trial is taking place in Manhattan federal court and is expected to continue into the coming weeks.
