Lawyer Breaks Down Diddy’s Charges, ‘Plea Deal’ Possibility and More

Criminal lawyer Paul Callan weighed in on the serious charges Sean “Diddy” Combs is facing in his sex trafficking and racketeering conspiracy trial.

“The charges against him are severe,” Callan, who is not involved in the case, said to Us Weekly in an exclusive interview on Thursday, September 19. “If convicted, he can expect to spend most of his remaining life behind bars. Federal prosecutors generally obtain guilty pleas or convictions after trial in more than 90% of the cases they bring.”

Diddy, 54, was arrested on Monday, September 16 in New York City after a grand jury indicted him following multiple sexual assault lawsuits and a federal investigation. The rapper, who pleaded not guilty, was denied bail and was remanded to stay at the Metropolitan Detention Center until his trial. A trial date for Diddy’s case has not yet been scheduled, per Deadline.

Callan explained that Diddy’s current situation in which he must remain in jail is “unusual” since “most federal criminal defendants are released on bond to await trial.”

“Prosecutors presented a strong case to both federal judges that Combs was likely to flee and/or threaten witnesses in the case if released,” he told Us. “In such cases, the federal courts will sustain pretrial incarceration. The lower court decision can be appealed but I believe a reversal of the lower court order is unlikely.”

However, the attorney, who has been practicing law in New York City for the last three decades, believes that Diddy’s case is “likely to move quickly through the court system” because of the seriousness of the charges.

Callen also shared that while a life sentence is “theoretically possible” for Diddy, it is “highly unlikely” since there were no deaths involved.

That said, “Given the severity of the charges, a lengthy jail sentence is a virtual certainty if he is convicted,” Callan reiterated. “A sentence of 10 to 20 years if convicted is likely.”

Currently, there are no talks of Diddy negotiating a plea deal. However, there is a chance for that to change, according to Callan.

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Years before two of Sean “Diddy” Combs’ homes were raided in connection to a federal sex trafficking investigation, there was conversation about what went on at the rapper’s residences. After the March 2024 raid made headlines, a clip resurfaced of Usher recalling his experience living with Diddy as a teenager. “I got a chance to […]

“Most defendants facing serious federal charges negotiate a plea deal rather than risking a harsher sentence after trial. He is likely to do the same,” the lawyer told Us. “Of course, much will depend upon the prosecutors’ willingness to negotiate. So far they appear to have a strong case and don’t appear to be in the mood to extend leniency. He is, of course, presumed innocent but will have a difficult time explaining his brutal beating of his ex-girlfriend, Cassie Ventura, in a California hotel hallway preserved on videotape for all to see.”

Callan was referring to the resurfaced 2016 video of Diddy allegedly assaulting Ventura, now 37, in a hotel. The security footage was released by CNN in May, and Diddy can reportedly be seen grabbing, shoving, dragging and kicking the singer while she was attempting to exit a hotel room. After the clip made headlines, Diddy released an apology video.

“It’s difficult to reflect on the darkest times in your life, sometimes you gotta do that,” Diddy said in a May Instagram video. “I was f—ed up. I mean, I hit rock bottom but I make no excuses. My behavior on that video is inexcusable. I take full responsibility for my actions in that video. I’m disgusted.”