Published on: October 21, 2025, 08:10h.
Updated on: October 21, 2025, 08:11h.
- Reports suggest Trump is contemplating a commutation of Diddy’s federal prison term.
- Betting markets are seeing increased interest in the possibility of Diddy’s release.
This month, Diddy was handed a four-year and two-month prison sentence, along with a $500,000 fine, after being convicted a month earlier on two counts related to the transportation for prostitution. New developments indicate that President Donald Trump may be considering a commutation of the sentence, potentially allowing the hip hop icon to regain his freedom shortly.
The entertainment news outlet TMZ reported that a “high-ranking White House official” has indicated Trump is inclined toward commuting Diddy’s sentence. However, a number of staffers within the White House have advised the president against intervening in this particular case.
“Trump will proceed as he sees fit,” the insider told TMZ, adding that the commutation could happen as soon as this week, potentially allowing Diddy to be released by the weekend.
Sean Combs, also known as Diddy, Puff Daddy, and P. Diddy, was found guilty by a jury for transporting former girlfriend Cassie Ventura, another past acquaintance, and several male sex workers for prostitution. He was acquitted of the more severe charges of racketeering conspiracy and sex trafficking.
Historical Ties Between Trump and Diddy
At 55, Diddy has maintained a cordial relationship with the former billionaire president over the years.
I was once a writer for MTV’s “Total Request Live,” where Diddy frequently made not-so-scheduled appearances. Trump also graced the show, interacting with Diddy at least once. Both New York power players, Trump was a star on his “Apprentice” series while Diddy was one of the most renowned hip hop artists and entrepreneurs globally, sharing friendly exchanges, laughter, handshakes, and photo opportunities backstage.
Historically, Diddy has supported Democratic candidates, advocating for Barack Obama and Joe Biden. He even established the “Our Black Party,” a grassroots initiative aimed at promoting Black candidates.
In 2012, Trump referred to Combs as a “good friend” and noted their harmonious relationship. However, both acknowledged that their interactions changed significantly when Trump entered the political arena.
The online betting market Kalshi suggests Diddy has a 23% probability of being granted a pardon or commutation, a significant increase of 14% within the last 24 hours. A comparable market, Polymarket, estimates Diddy’s chances at an implied 18%.
Recently, Trump commuted the sentence of the defamed Republican figure, George Santos.
Anticipated Appeal
Should Trump choose not to commute Diddy’s sentence, Combs will continue with the appeal process for his conviction and sentencing. A notice submitted in the Southern District of New York this week informs the court of an impending appeal.
The notice did not outline the specific reasons for Combs’ appeal, but his legal team has previously argued that the transportation charges should not apply in this situation.
Diddy has been in custody since September 2024.