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After his sentencing, Sean “Diddy” Combs continues to face life behind bars, a stark contrast to the glitz and glamour of his celebrity lifestyle. Reports from former inmates and insiders suggest that the hip-hop mogul approaches prison with humility. Combs has still found ways to maintain his influence and connections, using the experience as a period of reflection. In October 2025, a former inmate who spent time with Combs revealed what Combs said about his personal regrets. Here’s what the mogul revealed.

Sean ‘Diddy’ Combs regrets his drug use, according to an ex-inmate

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Sean “Diddy” Combs remains behind bars until May 8, 2028. He’s currently at the Metropolitan Detention Center in Brooklyn, New York, where he’s remained since his arrest. Former MDC inmate Raymond Castillo spoke on PopCrime TV with Lauren Conlin about his personal experience with Combs while living with him in prison.

“He was someone who really cares,” Castillo noted of Combs’ demeanor, noting that Combs was “approachable” to other inmates. “If you approached him, ask him for any advice, or anything like that, he’ll answer you 100%. And he was always willing to help.”

Castillo added that Combs prioritized helping other inmates in the MDC. And the hip-hop mogul would offer his advice without any negativity or drama. During the conversation, Castillo added that Combs shared with the inmates about what he regrets in his life.

“He regrets — he would always tell us to stay away from drugs, because he said when you’re under the influence, you will make very poor decisions, and your mind will be clouded,” the former inmate revealed. “You’ll think you’re making the right choices, but you’re not, because you’re not 100% of yourself at that moment. And a lot of his mistakes came from that. And we could relate, because we all did drugs at one point in time in our lives.”

The hip-hop mogul launched an educational program for inmates

While incarcerated at the Metropolitan Detention Center, Brooklyn, Sean “Diddy” Combs launched a six‑week educational program entitled “Free Game with Diddy.” According to court filings, he scripted a 15‑page curriculum focused on business management, entrepreneurship, and personal development for his fellow inmates, Business Insider reports. The initiative was reportedly open to all inmates in his unit, and even included a Spanish interpreter to ensure broader accessibility.

Beyond simply delivering lectures, the program reportedly had an impact on the unit’s environment. According to defense papers, since the course began, rival groups in the dorm, including members of gangs such as the Bloods, Crips, MS‑13, Trinitarios, and 18th Street, were, in Combs’ words, “in one room learning and working together,” according to The Times. Combs’ attorneys cite this as evidence of positive behavior change, arguing it strengthens the case for his sentencing mitigation.

While speaking on PopCrime TV with Lauren Conlin, Raymond Castillo noted that reports of Combs unifying the prison are true. “Diddy was able to unify everybody,” he said.

Sean ‘Diddy’ Combs reportedly enrolled in the drug rehab program at the MDC

Sean “Diddy” Combs has reportedly taken steps to enroll in drug and behavioral rehabilitation programs while incarcerated, signaling a turn toward what his legal team frames as personal accountability and transformation. According to TMZ, Combs is participating in a drug‑abuse treatment program developed by Dr. Harry K. Wexler, alongside the “STOP” program (Specialized Treatment for Optimized Programming) aimed at addressing domestic violence and sexual‑assault issues.

CBS reported that Combs’ lawyers want Combs to move to FCI Fort Dix, a low-security prison in New Jersey. FCI Fort Dix has a residential drug treatment program. The program can help Combs “address drug abuse issues and to maximize family visitation and rehabilitative efforts,” Combs’ lawyer Teny Geragos wrote to the judge.

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