Diddy’s Trial Shocks with Usher, Obama, and J.Lo Name-Drops in Sex Trafficking Case

The trial of Sean "Diddy" Combs, charged with sex trafficking and racketeering, has taken a dramatic turn as week three unfolds, with a parade of A-list celebrities entangled in the testimony. From former President Barack Obama to music icons like Usher and Jennifer Lopez, the courtroom has become a stage for high-profile name-dropping, revealing a tangled web of relationships and allegations.

The trial, which kicked off on May 5, 2025, with jury selection, has seen intense testimony from Diddy’s former assistants, ex-girlfriend Cassie Ventura, and other associates. One jaw-dropping moment came when former assistant David James testified that Diddy carried dozens of pill bottles, including ecstasy pills shaped like Obama’s face. The revelation painted a bizarre picture of excess, raising eyebrows about the mogul’s lifestyle.

Dawn Richard, formerly of Danity Kane, delivered chilling testimony about a dinner in West Hollywood where Diddy allegedly punched Cassie in the stomach during a heated argument. Richard noted that Usher, music executive Jimmy Iovine, and Ne-Yo were among the celebrities present, highlighting the public nature of the alleged abuse. Cassie herself emerged as a key witness, detailing a 2011 incident where Diddy, enraged by her brief romance with Kid Cudi, allegedly orchestrated a break-in and car fire at Cudi’s home—claims the judge later instructed the jury to disregard.

The late Biggie Smalls also surfaced in testimony, with Diddy’s use of the alias “Frank Black” linked to Biggie’s nickname “Frank White.” Another assistant, George Kaplan, revealed that Diddy treated Biggie’s birthday as a paid holiday at Combs Enterprises, underscoring the rapper’s lingering influence. Meanwhile, Cassie’s former makeup artist, Mylah Morales, who worked with Rihanna and Jennifer Lopez, testified about seeing injuries on Cassie’s face in 2010, further fueling allegations of abuse.

The trial also touched on Diddy’s jealousy, with testimony suggesting he suspected Cassie was involved with Michael B. Jordan during a 2015 breakup. Even Britney Spears made a cameo in the narrative, mentioned as a guest at Cassie’s 21st birthday party, alongside producer Dallas Austin. As the trial continues, it exposes not just Diddy’s alleged crimes but a broader culture of power, control, and celebrity in the music industry.