Diddy Leans on Prison Classroom in Leniency Bid as Sentencing Nears

Sean Combs, the rapper and business executive known as Diddy, is leveraging a prison classroom program as part of a sentencing submission. In the court filing, his lawyers say he has been running a six-week entrepreneurship course at the Metropolitan Detention Center in Brooklyn, called Free Game with Diddy, designed to give fellow inmates foundational knowledge in business management and insights into Combs' rise to a global business leader.

According to the filing, the class was taught in a MDC classroom with a chalkboard and whiteboard as part of the Adult Continuing Education program. It notes that participants developed skills intended to help them thrive in competitive environments and that Diddy did not receive payment for teaching. The filing highlights eight inmates who took the course and wrote letters describing it as lifesaving and praising Diddy's influence, including Arturo Santiago, Douglas Welch, Wellington Eustate, Didier Rios Galinda, Charles Scruggs, Recaldo Fray, Corey Batchelor and Raymond Castillo. Santiago is accused of killing a man inside the MDC while already serving time for gun and drug offenses; Welch is described as an accused pimp. The letters portray Diddy as bringing purpose and discipline to the unit and as forming friendships with inmates during his 14 months at the MDC.

On the course's objectives, the filing says Free Game with Diddy is a six-week program designed to equip participants with essential skills in business management, entrepreneurship and personal development, including exclusive insights into Combs' journey from humble beginnings to a globally recognized icon. The summary notes that the eight letters describe progress in health, discipline and goal setting, and that the participants learned practical tools to launch and manage new businesses, with emphasis on resilience, decision making, accountability and adaptability, all framed by Diddy's storytelling.

Prosecutors have charged Diddy with two counts of transportation to engage in prostitution, but the jury cleared him of the more serious counts of sex trafficking and racketeering. He still faces up to 10 years in prison on the transportation counts. The sentencing is scheduled for Oct. 3, with prosecutors expected to file their sentencing submission on the following Monday. Before the arrest last year, Diddy built a fortune estimated at about $400 million from ventures such as the Sean John fashion label and marketing contracts with Ciroc vodka, as well as launching the careers of stars including Mary J. Blige. The defense filing emphasizes the prison program and inmate testimonials as evidence of his positive influence and argues for a sentence of time served.

Court records indicate the program ran on a first-come, first-served basis and used a chalkboard and whiteboard for instruction. Participants reportedly wrote essays showing how they could apply the class material to their long-term goals. The course outline includes motivational lines and practical steps such as setting a short-term goal and planning how to achieve it. The notes also say eight inmates wrote to praise the course, including individuals charged with serious offenses, and describe Diddy as providing motivation and support and helping others in the unit. The filing states that Diddy has developed friendships with Santiago, Eustate and Castillo and helps others who are less fortunate at the facility, a detail prosecutors are expected to weigh as sentencing arguments unfold.