What Was It Like Taking Diddy’s Business Course In Prison? A Former Inmate Speaks Out

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So, before Diddy started his four-year sentence at Fort Dix, he was held at the Metropolitan Detention Center in Brooklyn, and reports came out about some really tough conditions he faced there. But it turns out he wasn’t just surviving – he was actually making the most of his time. Apparently, he taught an entrepreneurship class to fellow inmates. And now, one of his former students is sharing what it was like learning from a Grammy-winning teacher behind bars. It’s a fascinating story about finding opportunity even in the most challenging circumstances.

While incarcerated at the MDC, 56-year-old rapper Diddy created a program called “Free Game With Diddy” to help fellow inmates. Raymond Castillo, a former participant, told Us Weekly that the course focused on teaching prisoners how to develop a practical and achievable plan for success, and understanding the dedication required to reach their goals. Castillo described the class as deeply impactful, helping him and others find purpose and meaning in life and learn how to achieve success.

According to Castillo, Combs wasn’t just a performer in the class—he expected students to actively participate by taking notes, sharing them with others, and reading for an hour daily. He even gave homework assignments. Castillo recalls that Combs would review the notes, offer advice on how to use the information in real life, and often used personal stories to illustrate his points. Castillo also shared Combs’ reasons for creating the course.

You know, he really struck me when he talked about wanting to help people. It was like he’d finally figured things out – that he wasn’t just here by chance. He genuinely felt he had a purpose, and through helping others, he rediscovered what truly excited him, what he loved doing again. It was incredibly moving.

In September 2024, Diddy was arrested as part of a federal investigation into sex trafficking. His trial started in May 2025, and in July, the jury reached a split decision. He was found guilty of two charges related to transporting individuals for prostitution, but cleared of more serious accusations of sex trafficking and racketeering. Diddy received his sentence in October, after publicly apologizing to those who had accused him of wrongdoing.

Before the hearing, Judge Arun Subramanian received letters from incarcerated individuals who praised Sean Combs and shared their positive experiences in his class. Raymond Castillo, who previously discussed defending Combs during a knife attack attempt, explained that the class has helped him since his release from prison. He stated that it has put him on a positive track and given him a clear plan for the future. Castillo also described how the course improved the atmosphere within the prison.

After that, things went very well. Diddy helped bring everyone together, as the group was previously quite divided. People like counselors, case managers, and assistant wardens who observed his classes noticed he was successfully uniting people from all different backgrounds and races in a single space.

Sources say Diddy is actively involved in programs at Fort Dix prison. He works in the chapel, similar to Todd Chrisley during his time in Florida, and also helps with laundry. He’s also enrolled in a drug treatment program to address substance abuse. It’s currently unclear if he plans to bring back his “Free Game With Diddy” show.

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2025-11-17 20:08