Sean “Diddy” Combs has failed in his attempt to overturn a felony prostitution-related conviction, setting the stage for a sentencing that could see the hip-hop mogul spend more than a decade behind bars.
A U.S. District Court judge in Manhattan dismissed Combs’ appeal this week, ruling that there was “overwhelming evidence of Combs’ guilt” in relation to his treatment of two former girlfriends, singer Casandra Ventura, known professionally as Cassie, and a woman identified in court only as Jane.
Prosecutors detailed how Combs organised what he called “Freak Offs”, drug-fuelled sex shows involving male escorts transported across state lines to perform with his girlfriends while he watched, recorded, and pleasured himself. Ventura and Jane testified that Combs physically assaulted them and threatened to cut off financial support if they refused to participate.
“The government proved its case many times over,” Judge Arun Subramanian wrote, rejecting Combs’ argument that evidence from acquitted charges, including racketeering conspiracy and sex trafficking, had unfairly influenced the jury.
Combs, 55, was convicted on 2 July of two counts of transportation to engage in prostitution after an eight-week trial. He maintains his innocence and plans to appeal. Prosecutors have requested a sentence of 11 years, while his defence team has asked for no more than 14 months, a term that could see him released this year given time already served since his September 2024 arrest.
In seeking the harsher sentence, prosecutors portrayed Combs as a man leading a double life. “The defendant tries to recast decades of abuse as simply the function of mutually toxic relationships,” they wrote. “But there is nothing mutual about a relationship where one person holds all the power and the other ends up bloodied and bruised.”
Ventura, in a letter to the court, described how Combs used “violence, threats, and drugs” to trap her into these so-called performances, beginning when she was just 19. “Sex acts became my full-time job,” she wrote. “His power over me eroded my independence and sense of self until I felt I had no choice but to submit.”
Combs’ legal team also argued that the Mann Act, the statute underpinning his conviction, required a financial motive or personal participation in the prostitution itself. The judge dismissed that claim, clarifying that Combs’ intent and the escorts’ financial motivation were sufficient for conviction. He added that requiring direct participation “would narrow prostitution almost out of existence,” even shielding brothel owners from prosecution.
The judge further rejected Combs’ claim that his actions were protected under the First Amendment as “an amateur pornographer,” stating that “conduct does not become legal just because he filmed it.”
Combs’ sentencing is scheduled for 3 October, and unless an appeal dramatically alters the course of events, one of hip-hop’s most powerful figures could soon be facing over a decade behind bars.
