Sean "Diddy" Combs appeared in a Manhattan federal courtroom on Friday to make his fourth attempt at securing bail while facing federal charges of racketeering and sex trafficking. The 55-year-old entered the courtroom in a khaki jail-issued outfit and smiled and waved toward his family, including his seven children and his mother, Janice Combs, who had gathered in the second row of the gallery to show their support.

Diddy's legal team petitioned U.S. District Judge Arun Subramanian to release him on a $50 million bond, backed by his $48 million Miami mansion. The plan included extensive restrictions, such as 24/7 monitoring, home detention, no internet or phone access, and a pre-approved visitor list limited to family members. His lawyers argued the new proposal was "far more robust" than previous requests.

Combs has been denied bail three times previously, with the most recent denial occurring on September 18. During that hearing, Judge Andrew Carter refused the bail request after prosecutors presented evidence they said demonstrated "clear and convincing evidence" of Combs' danger to the community. Despite his legal team's assurances that Combs is not a flight risk, prosecutors with the Manhattan US Attorney's Office have argued that Combs is an "extreme danger to the community" and have accused him of tampering with potential witnesses in the case. 

Prosecutors claim Combs led a "depraved criminal empire" for over a decade, using his music label, Bad Boy Records, as a front for illegal activities. They allege he organized events referred to as "Freak Offs," during which women were coerced into participating in drug-fueled sexual encounters. Evidence reportedly seized from raids on his Los Angeles and Miami properties includes narcotics and over 1,000 bottles of lubricant and baby oil, which prosecutors claim were used during these events.

Combs has pleaded not guilty to all charges, which include sex trafficking, racketeering, and transportation to engage in prostitution. His lawyers have maintained that the encounters described in the indictment were consensual and that the government's case is overstated.

Friday's hearing marked a pivotal moment for Combs, as his family and supporters filled the courtroom. His twin daughters, D'Lila and Jesse Combs, were among the family members who watched as he entered the courtroom and acknowledged them with smiles and waves. Combs' legal team emphasized his ties to the community and argued that keeping him in custody unfairly impedes his ability to prepare for his trial, which is scheduled for May 2025.

Judge Subramanian has yet to issue a decision on Combs' latest bail request, though a ruling could come as early as the end of the day. If denied, Combs will remain at the Brooklyn Metropolitan Detention Center, where he has been held since his arrest.