Former Inmates Reveal Sean ‘Diddy’ Combs’ Most Daunting Prison Challenge

Sean 'Diddy' Combs' Biggest Challenge in Prison, According to Former Inmates
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Sean ‘Diddy’ Combs’ life behind bars will markedly contrast with his previous lifestyle. Here’s a glimpse of what awaits him during his incarceration.

Published on November 22, 2025

As a renowned producer and entrepreneur, Combs led a fast-paced life outside of prison. Now, his daily routine will slow significantly. His day will start at 6 a.m. and conclude at 11 p.m. Though he is reportedly taking on the role of a chaplain’s assistant, he will need to find ways to occupy his remaining free time, which former inmates say can become monotonous.

Former inmates say Sean ‘Diddy’ Combs will struggle with boredom in prison

Outside prison, Combs was a producer and entrepreneur. He lived a busy life. Naturally, his days in prison will be a bit slower-paced. Combs’ day will begin at 6 a.m. and end at 11 p.m. He is reportedly working as a chaplain’s assistant, but he will need to fill his free hours. Former inmates say that this can grow tedious.

“Days are structured, but not meaningful,” Tyler King, a former inmate at Fort Dix and creator of the prison reform program A Voice From Prison, told Us Weekly. “There are classes, books, and limited programming, but not the rehabilitative environment the public imagines.”

Bill Baroni, a law professor who spent time in prison, said the biggest challenge he faced behind bars was “how slow time goes.” King noted that it’s essential to find a hobby to pass the time.

“Time is spent staring at TVs, pacing or staying glued to contraband phones,” he said. “Working out and reading are lifelines.”

Combs is reportedly spending time walking and talking to God. He also plans to teach a class on entrepreneurship.

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