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Once upon a time, years before either Hollywood heavy hitter found themselves in serious legal trouble, Harry Weinstein and Sean ‘Diddy’ Combs ran in the same social circles and attended the same parties. They were actually photographed together multiple times over the years.

While there is no evidence they were close friends, their connection at events and the fact that their trials are running in New York City simultaneously have linked them in some way. We can’t help but wonder if the disgraced film producer and the troubled music mogul have crossed paths in prison. It doesn’t seem like it, and it seems unlikely they ever will, regardless of the outcome of their trials.

Harvey Weinstein’s rape retrail began weeks before Diddy’s sex trafficking trial

New York City’s courthouses are getting a workout with celebrity defendants. Harvey Weinstein’s retrial on sexual abuse and rape charges began in April. The disgraced film producer was initially convicted of abuse and rape charges in 2020 after multiple women stepped forward to accuse the powerful Hollywood executive of forcing himself on them. He also faced charges in California.

One year ago, the New York Court of Appeals overturned the conviction. The court said there were errors in the judicial process and requested a retrial. The retrial got underway last month, after several delays. Weinstein’s case is being heard at the Manhattan Criminal Courthouse. The courthouse is located on Centre Street in Lower Manhattan. Weinstein’s trial should wrap up in the next two weeks.

Diddy is facing a plethora of federal charges

Sean ‘Diddy’ Combs is also on trial in New York City, but his proceedings look slightly different. The record label founder is currently on trial for sex trafficking and racketeering at the Daniel Patrick Moynihan United States Courthouse. The federal courthouse is located on Pearl Street.

Diddy’s trial began last week with jury selection, with opening statements heard on May 12. The trial is expected to last eight to ten weeks. According to the New York Post, Diddy is facing the possibility of life in prison.

Have Sean ‘Diddy’ Combs and Harry Weinstein seen each other in prison?

While Harvey Weinstein and Sean ‘Diddy’ Combs have trials running concurrently, the film producer and the rapper could not be further apart in prison. After a full day in court, Diddy is returned to the Metropolitan Detention Center in Brooklyn. It is the only federal lockup in New York City. Diddy has been at the facility since his September 2024 arrest.

Weinstein leaves the courthouse and returns to a Bellevue Hospital prison ward. According to NBC, Weinstein was staying at Rikers Island until mid-April, when a judge granted his request to transfer to a hospital. Weinstein has several significant medical complications. Before his time at Bellevue Hospital, the film producer served his sentence at Wende Correctional Facility and Mohawk Correctional Facility, both in upstate New York.

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If Weinstein is found guilty during his retrial, he will return to a state prison. If Diddy is found guilty, he’ll serve his sentence at one of dozens of federal lockups. Things would not look much better for Weinstein if he were found not guilty during the retrial. Regardless, he won’t go free. He’ll likely be extradited to California to serve out a 16-year sentence for rape in that state. If Diddy is found not guilty, he’ll walk free. There is no scenario in which the two men who once drank and partied at the same industry events are likely ever to cross paths again.

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