Sean Combs Mentored Inmates in Jail, Teaching Them to Think Like a Mogul

Sean “Diddy” Combs spent part of his recent time in jail teaching fellow inmates about business, entrepreneurship, and personal development. The initiative, known as “Free Game With Diddy,” became a unique educational program inside the facility.

Court documents submitted this week included the course description, student testimonials, and a positive evaluation from the jail’s Unit Counselor. These materials were sent to Judge Arun Subramanian as Combs’ legal team seeks the most lenient sentence after his conviction on two felony prostitution charges this summer.

The documents highlighted the effectiveness of the program. As noted in the evaluation: “Mr. Combs received the highest possible ratings and the class was described as ‘excellent class, keep up the great work.’” Lawyers also stressed that the course had a meaningful impact on participants’ daily lives.

Free Game With Diddy

Instagram | @rap | In a unique jail program, Diddy taught business and personal development to fellow inmates.

The six-week course “Free Game With Diddy” intends to provide fundamental knowledge in entrepreneurship, company management, and personal development. Combs drew heavily from his personal journey, offering firsthand insights into becoming a globally recognized figure in the music and business world.

The course promises a rare perspective on overcoming obstacles, navigating corporate challenges, and building a successful enterprise. Participants explored strategies that have defined Combs’ career while reflecting on lessons applicable to their own lives.

Course Structure and Key Topics

The program included several thematic sessions, each emphasizing practical and motivational principles:

Successful People Do What Unsuccessful People Won’t Do focused on self-discipline, hard work, and managing one’s ego. The sub-topics included “Never be embarrassed — No ego,” “Out Work the Competition,” and “Ego — the conscious self/extreme.”

Another session, Just Do It, emphasized short-term goal setting and action planning, addressing questions like “How much?” and “How long?” In Time Waits for No Man, Combs stressed the importance of meeting deadlines and valuing time, including the lesson: “You can make money but you can’t make time.”

The class The Marathon 26.2 explored long-term success, teaching students about patience, responsibility, and the cost of achievement. Sub-topics included “Nothing happens overnight,” “Trust the process,” and “Heavy is the head.” Combs also delivered a bonus session, Can’t Stop Won’t Stop, which reinforced persistence with the simple instruction: “Don’t stop” and “Never give up.”

Real-World Insights and Self-Reflection

Students were asked to complete assignments, including essays reflecting on Combs’ career and their own strategies for long-term goals. While the course heavily featured Combs’ personal experiences, it encouraged participants to draw practical lessons for themselves.

Despite Combs’ controversial history, the program’s focus remained on actionable business skills. It highlighted the challenges of leadership, strategic thinking, and self-management, giving inmates a structured framework for professional growth.

Student Experiences

Testimonials emphasized the course’s impact. One inmate said, “Because of this class I have a purpose, something to look forward to every day.” Another highlighted Combs’ lessons on realistic goals and the importance of setting aside pride: “He has shown that small adjustments in daily life lead to major changes over time.”

Students also praised Combs’ ability to foster unity within the facility. “Even behind bars and with limited resources, I have witnessed this man bring together people from all backgrounds,” one participant shared. These reflections suggest the course contributed not only to practical skills but also to morale and collaboration.

Context and Considerations

Instagram | @hot97 | The “Free Game With Diddy” program offers motivational teaching and practical skill development to rehabilitate inmates.

While the program has received strong reviews, it exists alongside Combs’ legal and personal controversies. Previous incidents, including allegations of abuse, remain part of his public record. However, the course itself focused strictly on business, leadership, and personal discipline.

Combs’ lawyers included the program as part of their sentencing submission, arguing that it reflects positive contributions even during incarceration. The initiative demonstrates that he invested effort in educating others, despite the challenges of confinement.

Educational Impact Behind Bars

“Free Game With Diddy” represents a unique approach to rehabilitation and skill development within correctional settings. The program combined motivational teaching with practical applications, giving inmates tools for future endeavors.

By focusing on structured business lessons, Combs provided an alternative to typical jail programming. Inmates gained insights into entrepreneurship, time management, goal setting, and accountability—skills transferable both inside and outside the correctional system.

The submission of “Free Game With Diddy” to the court highlights its potential influence on Combs’ sentencing, demonstrating the value of positive engagement and rehabilitation efforts in legal considerations.

The initiative also underscores the role of mentorship and leadership behind bars. By sharing lessons from a successful career, Combs helped participants develop strategic thinking, discipline, and persistence, showing that actionable knowledge can inspire meaningful change.