Facing 10 years, Diddy pleads for release from jail after conviction for transporting escorts

Sean “Diddy” Combs, once a titan of the hip-hop industry, is now pleading with a federal judge to release him on a staggering $50 million bond as he awaits sentencing for prostitution-related offences. The 55-year-old music mogul was convicted earlier this month on two counts of transporting individuals across state lines for sexual encounters.

The request comes amid growing concern about conditions at Brooklyn’s Metropolitan Detention Centre, where Combs has been held since his September 2024 arrest. His defence lawyer, Marc Agnifilo, has called the facility dangerous and argued that Combs is being unfairly incarcerated compared to others convicted of similar crimes.

“Sean Combs should not be in jail for this conduct,” Agnifilo stated in a court filing. “He may be the only person in the United States currently jailed for being a ‘John’—and certainly the only one jailed for hiring adult male escorts for him and his girlfriend.”

In the United States, the term “John” is commonly used to describe someone who hires sex workers.

Combs was acquitted of more serious charges—including sex trafficking and racketeering conspiracy—after a widely followed trial in New York earlier this year. Those charges could have carried a life sentence, but the guilty verdicts still expose him to a maximum of 10 years behind bars.

His legal team argues that Combs does not pose a flight risk or threat to the public, and has offered to secure the bail amount using one of his luxury properties. They’ve also proposed house arrest, electronic monitoring, travel restrictions, and surrender of his passport to ensure compliance.

Despite these offers, prosecutors remain firm. They maintain that Combs is a flight risk and have raised concerns about past allegations of violence and witness intimidation. The court previously denied bail immediately after the 2 July verdict, with Judge Arun Subramanian stating that Combs hadn’t proven by “clear and convincing evidence” that he posed no danger to the community.

The disgraced mogul is now among a list of high-profile detainees at MDC Brooklyn, which has previously held R. Kelly, Ghislaine Maxwell, and Sam Bankman-Fried. For Combs, who once defined an era of pop culture with Bad Boy Records and global hits, the reality of confinement is stark.

His current legal troubles began unravelling in late 2023, with a series of lawsuits and federal raids. One such lawsuit accused him of sex trafficking and sexual assault. The criminal case, however, narrowed its focus to the transportation of individuals for prostitution.

Combs’s legal team argues that the relationships in question were consensual and adult, and that his prosecution is an outlier in terms of how such cases are typically handled. His lawyers note that most similar convictions result in bail being granted until sentencing, rather than pre-sentencing incarceration.

The court is now expected to rule on this latest bond request ahead of Combs’s sentencing date, scheduled for 3 October 2025. If denied again, he will remain in federal custody until then.

As legal experts and industry watchers await the decision, Diddy’s once-glittering career continues to unravel in real-time—a dramatic fall from grace now playing out in courtrooms instead of concert stages.