Before Sean “Diddy” Combs was transferred to New Jersey’s FCI Fort Dix to serve his four-year (50 month) sentence, he did time at the Metropolitan Detention Center in Brooklyn. It was reported that Combs dealt with some “horrible” elements during his stay at the MDC, though it’s since been revealed that he also used the time productively. As part of that, he also taught an entrepreneurship class for inmates. Now, a formerly incarcerated attendee is speaking out about what kind of teacher the Grammy winner was.
The 56-year rapper and New York native launched the “Free Game With Diddy” program while serving time at the MDC. Former pupil Raymond Castillo shared positive thoughts on the course while speaking with Us Weekly. Castillo said Diddy’s intention was to show inmates “how to make a realistic, successful plan and the sacrifices and the steps we had to take to see it through.” He also said the “impactful” class showed him and others “become successful in life and how everything in life has value and purpose and meaning to it.”
Castillo also said Combs required students to take and share notes and read books for an hour a day. The “Bad Boy for Life” performer also apparently assigned homework to those taking the course. Per Castillo, Combs also provided “give feedback on the notes and tell us how we can apply it to our everyday of living” and even use himself as an “example” while teaching certain lessons. As for Combs’ rationale for starting the class, Castillo shared the following thoughts:
He said people need help. And he believes he was put there for a reason. He said he found his purpose. He found his passion, his love again.
Diddy was arrested in September 2024 as part of a federal sex-trafficking investigation, and his trial began in May 2025. Upon the conclusion of the court case this past July, the rapper received a mixed verdict, for which he was convicted on two counts of transportation to engage in prostitution and acquitted of sex-trafficking and racketeering charges. The Sean John mogul’s sentencing hearing was held this past October and, before receiving his sentence, he apologized to those who’d made accusations against him.
Ahead of that hearing, presiding Judge Arun Subramanian also received letters from convicts, who voiced support for Sean Combs and detailed their experiences in his class. Raymond Castillo – who previously spoke about defending Combs amid that attempted knife attack – said he’s benefitted from the class since being released from prison. He also said that as a result of the class, he’s been on “the right path” and now actually has “a plan” for himself. Castillo also made claims about how the course shifted the vibe in the prison:
Everything was smooth after that. Diddy brought unity to the unit, because the unit was really divided. …. Even counselors, case managers, assistant wardens who came and sat down in the class saw he was unifying everybody from all cultures and races, all in one room.
Recent reports indicate that Combs has also been productive at FCI Fort Dix, as he’s reportedly working in chapel (a job Todd Chrisley also held amid his own prison stint in Florida). Aside from also being assigned laundry duty, Combs is also participating in the facility’s Residential Drug Abuse Treatment Program to assist with his substance abuse issues. Whether he’ll opt to revive “Free Game With Diddy” is unknown at this point.
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