It’s been three weeks since Sean “Diddy” Combs—convicted of two counts of transportation to engage in prostitution—was sentenced to 50 months in a federal prison. In that time, reports that President Trump was planning to commute his sentence have surfaced and been denied. And this week, according to yet more reports, the Bad Boy Records founder, 55, awakened with a knife to his throat.
But Diddy’s time in Brooklyn’s Metropolitan Detention Center predates both of those moments by more than a year. Following his arrest September 2024, he was denied bail and ordered held at the federal prison. And despite his lawyers' best efforts, he remained at the facility—known for its inhumane conditions—for the duration of his trial. Here’s everything that’s unfolded for Diddy behind bars since he was taken into federal custody.
Diddy’s Arrest (Sept. 16, 2024)
In early September, anticipating an indictment, Diddy traveled to New York and checked in to a hotel. The move came in the wake of a series of disturbing allegations from sexual abuse from multiple women, including Cassie, whose lawsuit he settled a day after it was filed. On Sept. 16, he’s arrested, and the following day, after he pleads not guilty, a judge orders him held without bail, calling him a flight risk. A $50 million bond proposal does not sway the court.
Denied Bail Again (Sept. 18, 2024)
For the second time in a week, the court refuses Diddy’s bail request, citing concerns over witness tampering.
A Third Attempt at Bail (Nov. 27, 2024)
Diddy’s request for bail is denied for a third time, with a judge once again citing the risk of witness tampering. Prosecutors also accused Diddy of reaching out to witnesses from jail via family members, whom he asked to cultivate “narratives” that could influence the jury pool, and of using other inmates' phone access to make calls, and using three-way calls to contact people who weren’t on his approved contact list.
Computer Access (Dec. 12, 2024)
In spite of this, Diddy is granted access to a laptop with pre-loaded court documents for his review. He can use the computer between 8 a.m. and 3:30 p.m. each day.
The Verdict (July 2, 2025)
After a trial that runs for nearly two months, Diddy is found guilty of two counts of transportation for prostitution and acquitted of more serious racketeering and sex trafficking charges. His sentencing is scheduled for Oct. 3, and he’s denied bail again.
Another Attempt at Bail (Aug. 4, 2025)
Awaiting sentencing, Diddy again makes the case for bail, and is again denied, with the court reasoning that a $50 million bond doesn’t change the fact that Diddy is violent and liable to do whatever he will “behind closed doors.”
Free Game in Lock-Up (Sept. 26, 2025)
According to documents his legal team submitted to the court, Diddy dedicated part of his time behind bars to instruction. Free Game With Diddy, a six-week 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,” the paperwork says. Among the bullets on the syllabus: “Successful People Do What Unsuccessful People Won’t Do.”
Pardon Talk (Oct. 6, 2025)
The Monday after Diddy is sentenced, President Trump says the convicted mogul requested a pardon. “A lot of people have asked me for pardons,” the commander in chief says. “I call him Puff Daddy; [he] has asked me for a pardon.”
Or a Possible a Commutation (Oct. 20)
TMZ reports that Trump was “vacillating” on a commutation, which wouldn’t pardon Diddy but would free him “as early as this week.”
Impossible, Says the White House (Oct. 21)
Less than 12 hours later, the White House Communications Office denies the report. though TMZ stands by its story.
Stabbed? (Oct. 22)
According to a friend, one night in MDC, Diddy woke up to a knife pressed against his throat. The incident, which the friend thinks was a warning, had come up during at Diddy’s sentencing hearing, with Diddy’s lawyers saying he was a high-profile target inside.
