How Can Diddy Get Away With Living a Luxury Life in Prison?
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Sean Combs
Image via Nicolas Richoffer / CC 2.0

Diddy reportedly living in ‘luxury’ in prison, has personal staff, private cook, masseuse, Hennessy, ‘the day he arrived, the party started’

“You can pretty much get anything except a key to the front door and a female.” 

A new report indicates that disgraced music mogul Sean “Diddy” Combs is living a better life in prison than most people on the outside. Reporting by NBC News claims that Diddy’s time inside the Fort Dix Federal Prison has been a cakewalk, as the prison has let him continue his “pampered lifestyle” without interruption.

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Diddy is currently serving a 50-month sentence for prostitution-related offences, but he’s said to be spending thousands of dollars each month to keep the party going. The report comes courtesy of four men who say they spent time in Diddy’s unit.

One of them explained that even to seasoned criminals, Diddy’s situation is bizarre: “This is not some normal **** you see in jail. This is some rich ****. It looks crazy, but again, it’s Diddy.” They specifically allege that Diddy has hired other prisoners to effectively work as his staff. Men cook and clean for him, make his bed, clean the bathroom and showers before he uses them, and give him “Chinese-style” massages.

“It looks crazy, but again, it’s Diddy”

This loyalty is said to be funded by him putting thousands of dollars in the men’s commissary accounts, done in coordination with Diddy’s friends on the outside.

They also allege that Diddy’s high life is supported by the guards. As per TMZ, he maintains “a stash of high-end liquor” said to be smuggled into the prison by staff. One of the men said he’d drunk Hennessy with Diddy. As one put it, “You can pretty much get anything except a key to the front door and a female” 

Entertainment also seems fairly easy to get. Diddy reportedly has contraband cellphones he uses to browse Instagram and view pornography, as well as a “jailbroken” tablet he uses to watch movies and documentaries. This apparently also includes him watching Netflix smash, Sean Combs: The Reckoning, about the very behavior that landed him here.

Diddy’s time in prison hasn’t been all smooth sailing – he was sent to solitary confinement in july after getting into a fight – but it certainly sounds like his sentence is passing easily, while also bringing the men incarcerated with him along for the ride. As one said, “Pretty much the day he arrived, the party started.”

Diddy’s spokesperson told NBC that this is merely “ordinary prison life”: The continued scrutiny of every mundane detail of Sean Combs’s life in prison has reached the point where the media characterizes ordinary prison life as news. The only real news is that Sean continues to serve his sentence while awaiting the court’s decision on his appeal.” As per court documents, Diddy is currently scheduled to be released on Jan 21, 2028.


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David James
I'm a writer/editor who's been at the site since 2015. I cover politics, weird history, video games and... well, anything really. Keep it breezy, keep it light, keep it straightforward.