Sean “Diddy” Combs has found a new passion behind bars, teaching aspiring inmates entrepreneurial skills to use upon their release.
Raymond Castillo, a former inmate at Brooklyn’s Metropolitan Detention Center with Diddy, 56, spoke to Us Weekly exclusively about the positive change the rapper’s “Free Game With Diddy” program brought to the jail.
“Everything was smooth after that. Diddy brought unity to the unit, because the unit was really divided,” Castillo told Us on Thursday, November 13, adding that “everybody was segregated” until the disgraced mogul started the program.
“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,” he continued.
Sean “Diddy” Combs will continue to teach aspiring entrepreneurs while locked up at Fort Dix, and Us Weekly can exclusively reveal details of what the six-week course will look like. His publicist Juda Engelmayer confirmed to Us that the “Free Game With Diddy” class the incarcerated music mogul, 56, taught at Brooklyn’s Metropolitan Detention Center […]
Castillo said Diddy showed his fellow inmates “how to make a realistic, successful plan and the sacrifices and the steps we had to take to see it through.”
He added that these fundamental lessons taught them to “become successful in life and how everything in life has value and purpose and meaning to it.”
“The class was just so impactful,” Castillo noted, sharing that Diddy would give them homework, which included reading books for an hour a day, taking notes and sharing those notes with the class. Diddy would then “give feedback on the notes and tell us how we can apply it to our everyday of living.”
Castillo said that Diddy’s class was “empowering us and giving us hope.”
Sean “Diddy” Combs Dia Dipasupil/Getty Images
“The class impacted everyone. It made everyone think differently, value themself more and get more in touch with the side that loves yourself,” he told Us. “It made you want to do better.”
The six-week course that Diddy taught at MDC Brooklyn, which he’s bringing to his new prison at Fort Dix, also impacted their teacher.
“He said people need help. And he believes he was put there for a reason,” Castillo explained about Diddy. “He said he found his purpose. He found his passion, his love again.”
When Diddy is released from prison, he allegedly told Castillo he wants to visit juvenile detention centers and implement his “Free Game” program for troubled youth.
A new glimpse of Sean “Diddy” Combs as an inmate in federal prison has been revealed. CBS News published Diddy’s intake photo at FCI Fort Dix in New Jersey on Monday, November 10. The former music mogul, 57, was transferred to the facility on October 30, several weeks after being sentenced to four years behind […]
According to Castillo, Diddy used his personal experience to bond with the inmates during his lessons.
“He wouldn’t only show us the good moments. He would tell us to take him as an example. He would tell us the bad moments, tell us to stay away from drugs because drugs were going to lead us to failure,” he said.
Castillo also credits the class for helping him land a job just weeks after his release.
“Ever since I got out, I’ve been on the right path. I’m way more prepared. Now, I actually have a plan,” he stated. “That’s all due to the class. Without the class, this would not have been possible.”
Sean “Diddy” Combs has reportedly been undergoing therapy while in prison. Diddy, 55, has enrolled in self-improvement programs to address his past drug use and violence against women, according to TMZ. The outlet reported that Diddy, who is being held at Brooklyn’s Metropolitan Detention Center, is participating in the STOP Program, which helps inmates learn […]
Diddy’s publicist Juda Engelmayer previously told Us that the “Free Game With Diddy” class “will be the same or very similar” to the one he’ll be instructing at Fort Dix.
The syllabus, obtained exclusively by Us, outlined the course lessons, with one class solely focused on no egos.
Diddy was arrested in September 2024. He was charged with racketeering conspiracy, sex trafficking and transportation to engage in prostitution. He pleaded not guilty and denied all the allegations against him.
In July, he was convicted on two counts of transportation but acquitted on the remaining charges. Last month, he was sentenced to a total of 50 months in prison. The 13 months he spent at MDC will count toward his sentence.
The rapper was transferred to New Jersey’s Fort Dix in late October. His release date was recently pushed back following accusations that he was caught drinking. Engelmayer, however, denied the alcohol claim to Us.
Diddy is now expected to be released on June 6, 2028.
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