Sean “Diddy” Combs faced explosive testimony in his Manhattan federal courtroom Monday as high-profile celebrities including Usher and references to former President Barack Obama emerged during the third week of his sex trafficking and extortion trial.
The rap mogul sat silently as former associates, assistants and his ex-girlfriend Cassie Ventura delivered damning testimony about alleged criminal activities spanning years of his career in the music industry.
Combs faces serious federal charges including one count of racketeering conspiracy, two counts of sex trafficking and two counts of transportation to engage in prostitution.
The 55-year-old defendant has entered not guilty pleas to all charges in Manhattan federal court.
The trial began March 5 with jury selection, followed by opening statements delivered May 12.
Prosecutors have systematically built their case through testimony from multiple witnesses with direct knowledge of Combs’ alleged criminal enterprise.
Judge Arun Subramanian has presided over proceedings that have drawn significant media attention due to the high-profile nature of both the defendant and the celebrity witnesses called to testify.
Former assistant David James provided disturbing testimony May 20 about Combs’ drug habits, stating the rapper routinely carried “25 to 30” unmarked pill bottles on his person at all times during their working relationship.
Assistant U.S. Attorney Christine Slavik questioned James extensively about the contents of these bottles, prompting detailed testimony about ecstasy pills shaped like political figures that Combs allegedly consumed regularly.
“There were various pills, but there was one that was in the shape of a former president’s face,” James explained under oath when asked to describe the ecstasy he witnessed Combs consuming throughout their professional association.
When prosecutors pressed for specifics about which former president’s likeness appeared on the narcotics, James identified Barack Obama as the face depicted on the pills that Combs allegedly carried and used.
The testimony about Obama-shaped ecstasy pills represents one of the most unusual pieces of evidence presented during the ongoing federal prosecution of the music industry titan.
Former Danity Kane singer Dawn Richard delivered explosive testimony about a violent incident involving multiple celebrities, including Usher, at a West Hollywood dinner gathering that has become central to the prosecution’s case.
Richard described witnessing Combs punch Cassie Ventura in the stomach during what appeared to be a private argument at the celebrity-filled event attended by numerous music industry figures.
“We were having a private conversation, and we were all sitting, eating at the tables together,” Richard testified before the packed courtroom.
“When I say we, I mean some Bad Boy, some of our other label, and even some celebrities were in the room. And they were secretly arguing, and he punched her in the stomach.”
Richard continued her detailed testimony, describing the immediate aftermath of the alleged assault: “She immediately bent over and then was–he was–he told her to leave because I could see him point out, and she went out and left the room.”
The witness identified multiple high-profile attendees at the dinner, including Usher, music executive Harve Pierre, two of Combs’ assistants, the rapper’s security team and Kaleena Harper.
Under cross-examination by defense attorneys, Richard admitted she initially failed to identify all celebrity guests present at the gathering, raising questions about the completeness of her initial testimony.
“Usher was there, Jimmy Iovine was there, Ne-Yo came through,” Richard eventually disclosed after persistent questioning from defense counsel.
“There were a few others, too. I don’t recall those people, but those are the ones I remember talking to.”
Rapper Kid Cudi provided compelling testimony May 22 about alleged retaliation following his romantic relationship with Ventura, which prosecutors claim triggered Combs’ violent response and criminal behavior.
Fox News reported that Cudi testified about a suspicious break-in at his residence occurring the same day Combs discovered the relationship between Cudi and Ventura through electronic communications found during a “freak off” party.
The rapper alleged his vehicle was deliberately set on fire approximately one month after the break-in incident, prompting him to directly confront Combs about potential involvement in what he believed was targeted harassment.
“I reached out to Sean Combs after my car had caught fire and … finally told him that we needed to meet up to talk,” Cudi testified before the attentive jury.
“He had been wanting to talk to me. So, after the fire, I was like, ‘This is getting out of hand/ I need to talk to him.’”
When prosecutors asked why Cudi specifically contacted Combs following the vehicle fire, the rapper stated he believed Combs “had something to do with it,” directly implicating the defendant in alleged retaliatory criminal acts.
Judge Subramanian, however, sustained a defense objection to this testimony, instructing jurors to disregard Cudi’s response about Combs’ alleged involvement in the arson incident.
Central to the prosecution’s case are allegations surrounding “freak off” parties where Combs allegedly forced attendees to perform sexual acts and consume illegal substances in what prosecutors describe as a systematic pattern of abuse.
These gatherings reportedly targeted up-and-coming artists signed to Combs’ Bad Boy record label and personal employees who faced coercion to participate in criminal activities under threat of career destruction.
Testimony revealed Combs allegedly monitored electronic communications of party attendees, including searching through phones to discover personal relationships that might threaten his control over artists and associates.
The prosecution claims these parties were integral to Combs’ alleged criminal enterprise, serving as venues for sex trafficking and other federal crimes that form the basis of the current charges.
Kid Cudi was first mentioned in testimony May 14 when witnesses described Combs discovering email correspondence between the rapper and Ventura during one of these controversial gatherings.
The trial has featured testimony from former Homeland Security Investigations agents who conducted the federal investigation that led to Combs’ arrest and indictment on the current charges.
Ventura’s mother also provided testimony, along with multiple former associates who worked directly with Combs throughout his decades-long career in the music industry.
