Diddy's Life After Prison Will Be A Far Cry From His Cushy Celeb Lifestyle

Unless Diddy's request for a pardon from Donald Trump is successful, his life after getting out of prison will look very different from the cushy celebrity lifestyle he's enjoyed.

Diddy was sentenced to just over four years in prison in October 2025 due to prostitution-related felonies. Reports list the terms that he'll have to comply with after his release, revealing that he'll have to adapt to newly regimented, highly surveilled lifestyle — something his time behind bars might help him prepare for. According to TMZ, Diddy is going to be supervised for five years after his sentence, which, pending an early release for good behavior, will likely conclude around 2029. During that time, the rap star will be forced to attend treatment programs for not only substance abuse, but also domestic violence — a central issue of his case. He also won't be allowed to own any guns or weapons, in addition to being forced to stay away from the people who testified against him, including his ex, Cassie Ventura.

But that's not all. According to NBC News, the terms of Diddy's post-prison release will be even stricter. In addition to the aforementioned, Diddy will also be forced to undergo drug testing within two weeks of his release, with surprise tests coming at his probation officer's discretion. Speaking of the terms of his probation, he'll also be forced to meet with his probation officer at any time, even during surprise drop-ins. So far, there's no language about the limitations regarding his social life, other than the fact that he won't be able to convene with other criminals during his time under his supervised release.

Between Diddy's disgusting prison diet and substandard and dangerous living conditions present at the Metropolitan Detention Center, he's obviously itching to become a free man again. When this happens, he hopes to celebrate his release in front of thousands of screaming fans. In an August 2025 interview with CBS News, the rapper's lawyer, Marc Agnifilo, said of his client's post-prison plans, "He's going to be back at Madison Square Garden." Diddy performed at the iconic venue during the Bad Boy Family Reunion Tour in 2016, and he planned to return there for a Verzuz battle with Jermaine Dupri in September 2023 — just two months before Cassie Ventura filed her bombshell lawsuit against him. However, the event never happened.

It remains to be seen whether Diddy's crimes will make him persona non grata in the music industry after he gets out of prison, dashing his MSG dreams. In addition to attempting a career relaunch, he plans to become more of a family man — at least according to his attorney. "I think he wants to get out of jail, reestablish a loving, present relationship with all of his seven children," said Agnifilio. So, could this mean Diddy is done partying?

For the past 30 or so years, Diddy, who owns a slew of ridiculously expensive things, has lived it up like the one-percenter he is. This includes sporting designer clothes, indulging in all his material whims, and of course, throwing lavish, celebrity-filled parties, the lore of which became the center of his sex-trafficking trial. He once joked about his infamous parties getting him into trouble one day. "You're going to hear about my parties, he told ET in 1999. "They're going to be shutting them down, they going to probably be arresting me."