Will Donald Trump Pardon Diddy? Bet On It Now

Sean “Diddy” Combs was sentenced on October 3, 2025, to four years and two months (50 months) in federal prison for two counts of transporting individuals for prostitution under the Mann Act, after being acquitted of more serious racketeering and sex-trafficking charges.

The case stemmed from allegations that he arranged and transported women, including ex-girlfriend Cassie Ventura, across state lines for sexual purposes. He has roughly one year credited for time already served and could be released in late 2027 with good behavior.

Diddy has since filed an appeal challenging the conviction, but his attorneys are seeking a much faster way of securing his release – a presidential pardon.

While a Diddy pardon may seem like a long shot, Trump has proven in the past that he can be moved to compassion.

Will Trump Pardon Diddy?

On October 17, 2025, President Donald Trump commuted the seven-year federal prison sentence of former Representative George Santos for wire fraud and identity theft, resulting in his immediate release after serving less than three months. Trump’s order also erased Santos’s restitution and probation requirements, calling him “horribly mistreated.”

While the Santos case has nothing to do with Combs, the pardon shows that there is potential for Trump to use his presidential powers, even for folks with whom he’s not aligned well.

Here’s the thing, though. Trump does know Diddy.

Trump and Combs have a long history rooted in New York’s elite social and business circles dating back to the late 1990s. Trump attended Diddy’s 29th birthday party in 1998, calling him “legendary.”

They were frequently seen together at exclusive events in the late 1990s and early 2000s, with Trump often speaking fondly of Diddy, calling him a “good guy” and a friend during appearances on “The Celebrity Apprentice.”

However, their relationship reportedly cooled after Trump entered politics, with Diddy making critical remarks about him. Will Trump now come to Diddy’s rescue? Entertainment sportsbooks have weighed in with prop bets on the outcome.

Will Donald Trump Sr. Pardon Sean “Diddy” Combs

• Yes +5000

Examining the odds offered in the latest entertainment prop bets reveals that there’s not much chance of Diddy’s sentence being commuted by the president. A +5000 moneyline converts to a 2% chance of success for Combs.

“There is zero truth to the TMZ report, which we would’ve gladly explained had they reached out before running their fake news… The President, not anonymous sources, is the final decider on pardons and commutations.”

White House Spokesperson

The assumption of a “no” outcome is so extreme that oddsmakers refuse to accept wagers on its potential.

When Will Sean “Diddy” Combs Be Released?

• On or Before November 7th, 2027 -120
• After November 7th, 2027 -120

Online sportsbooks are offering an over/under bet with a line set for November 7, 2027. The odds offer an equal probability that his release will occur before or after that given day.

BetUS Sportsbook (BetUS Review) | NBC News