Sean “Diddy” Combs, once celebrated as a titan of hip-hop, failed in his latest courtroom gamble. A federal judge in Manhattan has refused to overturn his felony conviction tied to prostitution-related charges—leaving the music mogul staring at a potential 20-year prison sentence.
Combs, 55, was found guilty in July after jurors heard weeks of testimony about what prosecutors described as his orchestrated “Freak Offs”—drug-laced sexual marathons where he allegedly paid male escorts to cross state lines and perform with his girlfriends, while he filmed the encounters. Though cleared of sex trafficking and racketeering charges, the conviction on transporting individuals for prostitution was enough to keep him locked in.
Defense lawyers argued the videos were nothing more than “amateur pornography,” a form of free expression shielded by the First Amendment. They stressed that Combs never personally engaged in the sexual acts. The judge, however, sided with prosecutors, who insisted that arranging and financing the travel was enough to secure a conviction—and accused Combs of using the videos as leverage, threatening to expose them if his girlfriends resisted participation.
The trial spotlighted testimony from R&B singer Cassie Ventura and another woman known as Jane, both of whom recounted being coerced and assaulted, with threats of financial abandonment hanging over them. Combs’ team admitted instances of violence but insisted that their involvement in the encounters was voluntary.
Combs, arrested on sex trafficking allegations in September 2024, has been held in Brooklyn’s Metropolitan Detention Center ever since. His sentencing is scheduled for October 3, where decades of his freedom now hang in the balance.
