Sean “Diddy” Combs’ former personal assistant, David James, testified on Tuesday (May 20) that the music mogul once took an ecstasy pill shaped like former US President Barack Obama’s face. Speaking under oath in Manhattan federal court, James said he regularly witnessed Combs consuming drugs—opiates during the day and ecstasy at night—while working for him from 2007 to 2009.
“He took a pill shaped like a former president’s face,” James said. When asked which president, he replied: “President Obama.”
James added that he frequently delivered narcotics and personal items such as condoms and lubricant to Combs’ hotel rooms, and sometimes sourced drugs for the artist and his entourage.
Allegations of coerced sexual “Freak Offs”
Federal prosecutors allege that Combs orchestrated drug-fueled, multi-day sex parties—referred to as “Freak Offs”—from 2004 to 2024, forcing women to participate. Prosecutors say his staff assisted by booking hotels, providing drugs, and facilitating payments to male sex workers.
Combs, 55, has pleaded not guilty to racketeering and sex trafficking charges. His attorneys acknowledge his past substance abuse and relationship issues but maintain that all sexual encounters were consensual.
Mother recalls bruises, threats, and $20,000 demand
On Tuesday, Ventura’s mother, Regina Ventura, emotionally described how Combs demanded $20,000 from her in 2011 after discovering Cassie had a relationship with another man. “I was scared for my daughter’s safety,” she said.
Jurors were shown photos of Cassie with bruises on her legs and back, as well as an email in which she claimed Combs threatened to release sex tapes and have her harmed. Regina Ventura said she took out a loan against her home to meet Combs’ demand, though the money was returned a few days later. The defense chose not to cross-examine her.
Exotic dancer testifies on hotel encounters
Also taking the stand was male exotic dancer Sharay Hayes, known as “The Punisher,” who said he performed sex acts with Ventura in hotel rooms while Combs watched. He said Ventura paid him between $1,200 and $2,000 for each session, which took place from 2012 to 2016.
Under cross-examination, Hayes said Ventura occasionally sighed as Combs gave her instructions, but added: “It seemed like there was consent there as far as I was concerned.”
Cassie testifies: Abuse and blackmail claims
Earlier, Cassie Ventura, known professionally as Cassie and a former long-term partner of Combs, testified last week that she participated in Freak Offs for nearly a decade. She claimed that while she initially complied to please Combs, he later blackmailed her with recordings of the acts.
“He used the videos to control me,” Ventura told the court.
Defense pushes back on narrative
Combs’ legal team is attempting to portray his relationship with Ventura as complex and not criminal. They showed jurors messages in which Ventura allegedly expressed willingness to engage in Freak Offs.
Legacy under scrutiny
Known by multiple stage names including Puff Daddy and P. Diddy, Combs rose to fame launching the careers of various artists. He became a billionaire and helped transform hip-hop into a mainstream cultural force.
He has been in federal custody at a Brooklyn facility since his arrest in September 2024. The trial continues.
