What Awaits Sean Combs After He’s Released From Prison

When Cassie Ventura filed her 2023 lawsuit accusing Sean Combs of sex trafficking and assault, Rolling Stone’s senior entertainment investigative reporter Cheyenne Roundtree began tracing the music mogul’s rise to power and allegations that had long circulated only in whispered warnings. Her reporting appeared in Rolling Stone’s May 2024 feature Bad Boy for Life: Sean Combs’ History of Violence , and in the HBO documentary The Fall of Diddy , for which she received a consulting producer credit. She later covered Combs’s criminal trial and partial conviction from start to finish. Now, in her debut book, Bad Boy for Life: The Rise and Fall of Sean Combs , due out Sept. 29 via Henry Holt , Roundtree offers a sweeping account of the label executive’s flashy ascent and staggering fall from grace .

In an exclusive excerpt, Roundtree takes readers inside Combs’ efforts to control his image from behind bars and how his “look-alike son” Christian Combs has been acting as his “proxy” at events such as the February 2025 funeral for Voletta Wallace , the mother of The Notorious B.I.G. , not always to the desired effect.

Roundtree writes that while Combs’ downfall triggered initial shock waves, it stopped short of generating a wider reckoning for the executives, producers, and gatekeepers who “enabled bad behavior to maintain the status quo.” The final chapter takes stock of the #MeToo movement, what may await Combs when he’s eventually released (the Bureau of Prisons currently predicts he’ll go home on Feb. 5, 2028), and how celebrity often functions as a form of social currency, buying the rich and famous a measure of leniency unavailable to the countless fans who helped make Combs a star.

Sean John Combs, as of this writing, is inmate number 37452-054 and counting down the days of his sentence at Fort Dix, a low-security federal prison in New Jersey. Combs spends his time working in the chapel library and participating in the prison’s residential drug abuse program. His team managed to pull serious strings to bypass the lengthy waitlist and typical time requirements to secure him a spot in the intensive five-hundred-hour course that can last between nine and twelve months. In addition to treatment, the program is highly sought after for another reason: Upon completion, inmates can reduce their sentences by up to a year. Editor’s picks The 250 Greatest Albums of the 21st Century So Far The 100 Best TV Episodes of All Time The 500 Greatest Albums of All Time 100 Best Movies of the 21st Century

Combs’ efforts to shorten his time behind bars have not been limited to prison programs. His appellate legal team has been aggressively searching for any and every legal avenue that would overturn the judge’s sentence, nullify the jury’s guilty verdict, or even discredit the very criminal law that Combs was prosecuted under. At the same time, some of his associates continued working behind the scenes to butter up well-connected figures in Washington, DC, hoping to earn the sympathies of Combs’ former associate President Donald Trump. “I was very friendly with him.