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Hip-hop mogul Sean “Diddy” Combs heads to trial for his federal court case in May 2025. The charges against Combs include racketeering, sex trafficking, and transportation to engage in prostitution. While he pleads not guilty to the charges, it seems proving his innocence might be an uphill battle. Here’s what O.J. Simpson’s lawyer had to say about Combs’ odds in court.

O.J. Simpson’s lawyer answered questions regarding Sean ‘Diddy’ Combs’ court case

Sean “Diddy” Combs’ legal team maintains Combs’ innocence despite the criminal and civil charges against him. Combs currently resides behind bars at the Metropolitan Detention Center in Brooklyn while he awaits his trial in May 2025. In addition to the federal charges against him, he has many accusers at the state level claiming he drugged and assaulted them in the past.

O.J. Simpson’s famous lawyer, Robert Shapiro, successfully defended Simpson from murder charges in 1994. A clip shared to The Art of Dialogue’s X account shows Shapiro answering questions regarding what he thinks of Combs’ case.

“First of all, I think there’s going to be a different group of charges than what he’s facing right now,” Shapiro said. “Anytime you’re in federal court, anytime you’re not on bail, you have an uphill battle.”

The lawyer added that he believes more superseding indictments will hit Combs. However, he doesn’t think it’s game over for the hip-hop mogul.

“Oh, there’s always a chance,” Shapiro added. “Every trial, you have a chance. You go in with the presumption of innocence. But federal court, New York, you’re in custody, it’s a tough battle. He’s got great lawyers. The system will decide. … Every case in federal courts is challenging.”

A superseding indictment could push the trial date

Sean 'Diddy' Combs attends the 2022 Billboard Music Awards at MGM Grand Garden Arena while wearing a white suit and dark sunglasses.
Sean ‘Diddy’ Combs at the 2022 Billboard Music Awards | Mindy Small/FilmMagic
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O.J. Simpson’s lawyer, Robert Shapiro, noted that Sean “Diddy” Combs might get hit with more superseding indictments. A superseding indictment amends and replaces the original indictment listing the formal charges against Combs. A grand jury usually approves a superseding indictment if there’s additional information or evidence.

Neama Rahmani, a former federal prosecutor, told Law&Crime Network that Combs’ trial set for May 2025 will likely get pushed in the event of a superseding indictment, especially if minors are involved.

“Minors present a completely different set of circumstances,” Rahmani said, according to DailyMail.com. “We know through his lawyers, Combs is arguing that the sexual activity happened, but it was consensual. Of course, for sex trafficking, you need one of those elements: force, thought, or coercion. Obviously, minors cannot consent to any sexual activity, so that would be a very different defense entirely.”

Sean ‘Diddy’ Combs’ lawyers want possession of the 9 ‘freak-off’ tapes from the prosecution

Sean “Diddy” Combs’ sex parties, known as “freak-offs,” are at the center of his court case. The prosecution had possession of nine of the freak-off tapes at the start of 2025. Combs’ attorneys want possession of the tapes, as they told federal judge Arun Subramanian that the footage shows “adults having consensual sex, plain and simple,” according to Forbes.

Attorney David Gelman discussed the tapes on The Trial of Diddy podcast. Gelman agreed that Combs’ attorneys should have access to the nine videos, as the prosecution has an “obligation to turn it over” if it’s evidence they plan to use.

Gelman noted that Combs’ ex-girlfriend, Casandra “Cassie” Ventura, was the original holder of the tapes. This could spell trouble for her credibility. “Diddy doesn’t have these videos — Diddy never had these videos,” he explained. “They are in the possession of Cassie. It does undermine a little bit. It undermines that she is an alleged victim. … If she had the videos herself, and not Diddy, that would definitely bring a red flag to the government, and that would definitely help if I’m Diddy’s attorney.”

How to get help: In the U.S., call the RAINN National Sexual Assault Telephone Hotline at 1-800-656-4673 to connect with a trained staff member from a sexual assault service provider in your area.