Sean "Diddy" Combs will stand trial Monday in New York on federal charges of racketeering conspiracy, sex trafficking, and transporting individuals to engage in prostitution, after rejecting a plea deal that could have reduced his sentence. The trial will feature explosive testimony from several key witnesses, including Cassandra "Cassie" Ventura, a male sex worker, and former romantic partners, according to individuals familiar with the case.
The hip-hop mogul appeared in federal court last week and confirmed his decision to proceed to trial, telling U.S. District Judge Arun Subramanian, "Yes, your honor," when asked whether he had reviewed the proposed plea agreement. Prosecutors indicated that the deal, which was not made public, would have required Combs to acknowledge responsibility in exchange for a lesser sentence. His attorney, Marc Agnifilo, stated the decision to reject the plea "was made jointly" and noted Combs will be allowed to appear in civilian clothing during the proceedings.
The criminal case is expected to center heavily on Ventura's allegations, which she first brought in a civil lawsuit filed in November 2023. Ventura, who signed with Combs' Bad Boy Records label as a teenager, accused him of physical and emotional abuse over a decade-long relationship. The government's indictment echoes many of her claims, including an alleged 2016 hotel assault in Los Angeles captured on surveillance footage. Last week, the judge ruled that the video could be introduced as evidence at trial, and prosecutors say a witness who filmed a version of the footage will testify.
Federal prosecutors allege that Combs ran a criminal enterprise that coerced women into "Freak Offs"-multi-day sex parties where participants, including male prostitutes, were often drugged and recorded. One male sex worker seen in explicit footage from these events is expected to testify, a source told CNN. Additional sex workers may also be called to the stand.
At least four of the prosecution's main witnesses have previously filed civil suits against Combs. While Ventura has chosen to testify under her real name, three other alleged victims will appear under pseudonyms for privacy reasons, according to court documents referring to them as "Victim-2," "Victim-3," and "Victim-4." A friend of Ventura's is also expected to testify, offering corroborating claims and alleging her own experience of violence by Combs.
The witness list remains under seal, but three sources familiar with the case confirmed the identities of several expected witnesses. The trial will not address Combs' broader legal exposure-he is currently facing more than 60 civil lawsuits-but will focus narrowly on charges brought in the federal indictment.
In statements to CNN, Combs' attorneys have pushed back forcefully against the allegations: "These are not new allegations or new accusers," they said. "These are the same individuals, former long-term girlfriends, who were involved in consensual relationships. This was their private sex life, defined by consent, not coercion."
Combs has pleaded not guilty to all charges and denied all civil allegations. Since his arrest in September 2024 following federal raids on his Los Angeles and Miami homes, he has been detained at Brooklyn's Metropolitan Detention Center. In court last week, he appeared visibly changed, with gray hair, glasses, and a diminished physical presence-far removed from his past image as a fashion-forward music mogul.
The judge issued a warning at Thursday's hearing after one of the victim's attorneys, Lisa Bloom, made public statements about the case. "We are days away from trial," Judge Subramanian said. "I will not tolerate anything that jeopardizes the defendant's right to a fair trial." Defense attorney Teny Geragos called Bloom's remarks "disturbing" and "improper," saying they risk prejudicing the jury pool.
Though many civil accusers won't be testifying, sources say their interviews with federal investigators over the past 18 months played a central role in shaping the prosecution's case.
