Diddy is preparing to launch a series of entrepreneurship and life skills classes across Miami in October—but only if a federal judge allows him to walk free.
The Hip-Hop mogul-turned-aspiring educator is scheduled to teach at six venues next month, including correctional facilities, libraries, and cultural centers, as part of a reentry program for formerly incarcerated individuals.
The catch? He’s still locked up at the Metropolitan Detention Center in Brooklyn and won’t know his fate until his sentencing on October 3.
Diddy created the curriculum through RE Entry One Inc., a nonprofit based in Miami that focuses on reducing repeat incarceration through education and mentorship.
His course, titled “Free Game with Diddy,” was first introduced while he was behind bars. It’s been praised by both inmates and staff for its focus on self-improvement, business acumen and personal growth.
His October itinerary includes stops at the Miami North Work Release Center on October 6, Sprouting to Success School on October 14, and two appearances on October 17 at the North Dade Regional Library and the Little Haiti Cultural Arts Center.
He’s also booked for South Bay Correctional Facility on October 23, the Rights Restoration & Expungement Fair on October 25 and Quest Workspaces in Downtown Miami on October 29.
The scheduled events are concentrated in underserved areas such as Little Haiti and Miami Gardens, where Diddy hopes to connect with people affected by the criminal justice system.
But his ability to show up hinges on a federal sentencing hearing in Manhattan.
In July, a jury acquitted Combs of racketeering and sex trafficking charges but found him guilty on two counts of transporting individuals for prostitution. Each count carries a maximum sentence of 10 years.
Federal prosecutors are pushing for an 11-year sentence, citing what they described as “violent and coercive behavior” revealed during the trial.
His legal team is requesting a significantly reduced term, possibly 14 months or even probation, arguing that Combs has demonstrated remorse, taken steps toward rehabilitation, and contributed positively through his educational efforts.
U.S. District Judge Arun Subramanian, who is overseeing the case, denied Diddy’s request for a new trial earlier this week. That decision kept Combs in federal custody, where he has remained for nearly 13 months.
Bail has been denied multiple times, with the court citing concerns about public safety and Diddy’s record of violence. Supporters, however, have rallied behind him, highlighting his work as a mentor, father and community figure.
In a letter submitted to the court, Giovanni Sairras, executive director of RE Entry One, described Combs’ teaching as “an extraordinary asset” that could help disrupt cycles of incarceration.
Whether Diddy will be able to fulfill his October teaching commitments now rests in the hands of Judge Subramanian. The sentencing hearing is scheduled for Friday, October 3.
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