Sean "Diddy" Combs will have another opportunity to argue for bail after being denied twice since his September arrest on federal charges of racketeering, sex trafficking, and transportation to engage in prostitution. U.S. District Judge Arun Subramanian set the hearing for November 22, giving the hip-hop mogul a third chance to persuade the court that he should be released pending his May 2025 trial.

The federal case against Combs, 55, alleges a pattern of coercive and violent behavior stretching back to at least 2009, involving "freak-offs"-extravagant, multi-day sexual encounters-prosecutors claim were marked by force, threats, and intimidation. Combs' attorneys maintain that all encounters were consensual and argue that accusations against their client are financially motivated lies.

"The evidence makes clear that the government's case is thin," Combs' lawyers contended in a November 8 filing. They pointed to video recordings and testimonies allegedly demonstrating consensual relationships, including a contested March 2016 video involving Combs and a key accuser identified as Victim-1. The defense also argued that fresh evidence undermines government claims of witness tampering and other obstruction efforts attributed to Combs.

Combs' legal team, led by Marc Agnifilo and Teny Geragos, has proposed a "far more robust" bail package. It includes a $50 million bond backed by his Miami home, strict home confinement either in Miami or New York, 24-hour GPS monitoring, no internet access, and prohibitions on communicating with employees or others who could be connected to the case. The proposal aims to alleviate judicial concerns about potential witness intimidation. "Under the proposed updated bail conditions, Mr. Combs would not have access to 'employees and friends and the like,'" stated the defense's latest motion, using Judge Subramanian's previous language.

Prosecutors, however, maintain that Combs remains a significant flight risk and a danger to the community. They must file a response to his latest bail request by November 15, with Combs' legal team set to reply by November 20. In previous hearings, federal judges sided with the prosecution, citing concerns that Combs could obstruct justice or influence witnesses. Subramanian is the third judge to consider Combs' bid for bail after his case was reassigned due to scheduling conflicts.

Combs has been held at the Metropolitan Detention Center in Brooklyn since his arrest on September 16 at a New York hotel. His trial, currently set for May 5, 2025, could see him facing life imprisonment if convicted. Outside the courtroom, Combs also confronts a growing number of civil lawsuits, which his defense claims further complicate his ability to prepare for trial. His attorneys have argued that restrictive conditions at the detention center hinder his access to discovery materials, which include extensive video and photographic evidence.

"The Bail Reform Act and the Constitution demand more," Combs' lawyers asserted, emphasizing their client's right to adequately prepare for his defense. Recent lockdowns and multiagency sweeps at the detention facility have exacerbated the challenge of mounting an effective legal strategy, they added.

The mounting civil suits also prompted Combs' team to request a gag order to prevent public statements by parties involved in either the criminal or civil cases. Judge Subramanian denied this motion on November 8, citing alternative measures Combs could pursue without imposing a broad restriction on speech. "The unprecedented relief that Combs seeks on this motion is unwarranted," the judge wrote.