Could Sean ‘Diddy’ Combs Still Make Bail Before Sentencing? Bail Bondsman Shares His Take

Bail bondsman Ira Judelson, often referred to as New York’s “fixer for the rich and notorious,” has prominently surfaced in the hip-hop mogul Sean “Diddy” Combs’ legal saga. Judelson, who’s previously posted bail for high-profile figures like Dominique Strauss‑Kahn, Harvey Weinstein, and Conor McGregor, was spotted in the courtroom during Combs’s federal hearings after the star was denied bail in his sex-trafficking case. So, does Judelson think Combs could face prison release before his sentencing on Oct. 3, 2025? Here’s what he thinks.

Bail bondsman Ira Judelson says whether he believes Sean ‘Diddy’ Combs could still make bail

In the aftermath of his July 2, 2025, verdict, Judge Arun Subramanian denied Sean “Diddy” Combs’ bail. Judge Subramanian cited compelling evidence of a “years‑long pattern of violence.” Combs’ defense team also admitted this behavior during the trial.

Ira Judelson, a bail bondsman known for putting together bails for high-profile figures, weighed in on Combs’ situation. Judelson spoke to Law&Crime about whether he believes Combs could still make bail before the sentencing hearing on Oct. 3, 2025.

“Is there a strong possibility? I would say, at this point, no,” Judelson explained. Earlier in the conversation, he noted that Combs’ attorneys brought him in for consultation.

“There’s a chance that he could be sentenced to time served,” Judelson noted. “Based under the law, he can be. He’d be incarcerated for over a year at that time. He could get a year and a day. There’s a chance that the judge could hit him on a high end. I don’t know.”

“Knowing Mr. Combs and the way he thinks, I don’t think anybody wants to be incarcerated,” the bondsman added. “You feel like, ‘I just won. I just won my freedom back. Why can’t I go to an apartment in New York and eat Chick-fil-A, or have a steak brought in,’ you know? … But, again, it all determines on whether or not a judge can do it, and whether or not this package that we’re going to put together, if we put it together back again, is sufficient enough for him to feel comfortable. He might say, ‘Look, I rather you just stay ’til October 3rd, and this is what I’m going to do.’ Again, I can’t determine what a judge thinks.”

Ira Judelson explained his discussion about a bail package with Sean ‘Diddy’ Combs’ lawyers

During his conversation with Law&Crime, Ira Judelson said he and Sean “Diddy” Combs’ lawyers discussed the aspects of a possible bail package.

“We talked about possibly renting out his plane and keeping it in Honolulu,” he said. “We talked about surrendering his passport, his family’s passports; we talked about putting up his house.” He added that he had discussions surrounding private security, a call log, and who intended to visit Combs.

“In Puffy’s case, the way we were putting it to the judge was we were going to have a call log,” he continued. “So, you could see who his calls were going to. We were going to try to take away his WiFi in the building, which would’ve been a lot easier. We would limit the people who would come see him. So, at the end of the day, we had cameras inside the apartment we were going to do, which our people were going to put up. … We were going to make it very, very tight.”

Judelson noted that he planned to “regroup” with the attorneys to discuss another possible bail package.

The bail bondsman explained how celebrities differ from other criminal defendants

Bail bondsman Ira Judelson explained how celebrities differ from others when it comes to criminal defendants. And the answer should come as no surprise.

“More demanding,” Judelson explained. “When you get the phone call from the lawyer, or whoever … a celebrity doesn’t want to spend an extra minute incarcerated. You know, things change so drastically. … They’re a little more demanding, and everybody’s looking to me to make it happen. … I work in chaos all day long. That’s my life.”

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. 

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