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Sean ‘Diddy’ Combs teaches entrepreneurship to inmates while awaiting sentencing

todaySeptember 28, 2025 38

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Sean ‘Diddy’ Combs has spent part of the past year teaching fellow inmates business management and entrepreneurship.

The rapper and producer, 55, convicted in July on two felony prostitution charges, faces sentencing on 3 October in Manhattan, and it has now emerged he spent time behind bars teaching a self-devised course titled “Free Game With Diddy.”

It has emerged in documents submitted to the court ahead of his sentencing, with Combs’ lawyers saying they have provided Judge Arun Subramanian with material they argue demonstrates the rapper’s positive influence while in custody.

They provided a course description, inmate testimonials and an evaluation from a unit counsellor that rated the programme “excellent”, according to Rolling Stone.

The publication said in a letter to the judge, Combs’ attorneys wrote: “Notably, the evaluation acknowledges Mr Combs as a tutor, gives him the highest possible ratings and concludes with ‘excellent class, keep up the great work.’

“Furthermore, as stated in our sentencing memorandum, this course has had a substantial impact on fellow inmates.”

The six-week programme is described as an “educational program designed to equip participants with essential skills in business management, entrepreneurship, and personal development”.

Course notes state: “The course offers exclusive insights into the journey of Sean ‘Diddy’ Combs, tracing his rise from humble beginnings to becoming a globally recognized icon and influential business mogul.”

Class outlines included sessions such as Just Do It, focused on setting goals and making plans, and Time Waits for No Man, about deadlines.

Another module, The Marathon 26.2, listed topics including “Nothing happens overnight,” “The price of success” and “Heavy is the head”. A bonus class, Can’t Stop Won’t Stop, was summarised with: “Don’t stop” and “Never give up.”

Assignments required students to write essays drawing lessons from Combs’ career.

Testimonials submitted to the court were positive.

One inmate wrote: “Because of this class I have a purpose, something to look forward to every day.” Another said: “He has showed us that it is the little adjustments to our everyday lives that add up to a big change.”

A third noted: “In a place of segregation (I) have seen Mr Combs bring unity to all races and ethnics groups no matter the background.”

The materials come as Combs’ defence team seeks a lenient sentence.

Prosecutors are expected to submit their own recommendation before the hearing.

BANG Showbiz

Written by: IOL News

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