‘You Mentioned…Diddy Was a Good Friend of Yours: Donald Trump Suggests He Would Pardon Diddy Saying He ‘Would Look at The Facts’ In His Old Friend’s Case
Donald Trump has never been shy about flexing his pardon power to help old friends and allies out of sticky legal situations. The list of people in Trump’s circle who are facing or could face federal charges is long, but there’s always room for more. On May 30, he teased the possibility of adding Sean “Diddy” Combs to the list, but only if he decides that Diddy is being “mistreated” by the justice system.
Presidential pardons are often controversial, but Trump’s comment still came as a surprise when he was asked about Diddy in a news conference.
“Back when you hosted ‘The Apprentice,’ you mentioned once in 2012 that Diddy was a good friend of yours. … He has since found himself in some very serious legal trouble. Would you ever consider pardoning him?” a reporter asked the president.
“Nobody’s asked. But I know people are thinking about it,” Trump replied from behind his Oval Office desk. “I think some people have been very close to asking.”
“First of all, I’d look at what’s happening … and I haven’t been watching it too closely,” Trump said about the trial, which started in May. He continued, “I would certainly look at the facts. I think if somebody was mistreated, whether they like me or don’t like me, it wouldn’t have any impact on me.”
Trump was referencing the “bust-up” of his friendship with Diddy, which he believed fell apart when he “ran for politics,” citing Diddy’s “nasty comments” about him in the media. “But it’s not a popularity contest,” he stated, before confirming that he’d consider granting clemency to the rap mogul.
Though the president said the two haven’t seen or spoken to each other in years, they once ran in the same circles in the Hamptons and New York City. “He used to really like me a lot,” Trump remarked. Trump was known to occasionally pop into Diddy’s lavish parties in the late ’90s and 2000s. The duo was together at the 2005 Art for Life Gala honoring Diddy at Trump’s Mar-a-Lago private club in Palm Beach, Florida. In 2008, they were photographed with first lady Melania Trump at a United Nations event. And when Diddy celebrated his 33rd birthday in the Moroccan city of Marrakech, Ivana Trump was one of 300 guests he flew over for the festivities.
It wasn’t just Diddy that Trump was close with back in the day. Celebrities, hip-hop stars, and business moguls like Trump all traveled in the same scene. Russell Simmons once enthused to New York magazine that “Donald has the best plane I ever seen.”
“These guys have done more for respect than anything,” Trump responded in the interview, referring to Russell and late hip-hop industry giant Andre Harrell. “Russell knows the market, he sees the future, and that’s the ultimate businessperson,” he gushed.
Combs was arrested in September 2024 and faces federal charges of racketeering and sex trafficking, which carry a possible sentence of life in prison. Just on May 29, his ex-personal assistant of eight years took the stand to describe several harrowing sexual assaults between 2009 and 2017, including at his 40th birthday party, where he poured her three vodka shots before attacking her and sticking his hand up her dress, according to The Hollywood Reporter.
In such a high-profile case and with such serious allegations, pardoning Combs would be a highly controversial move, even for Trump, although, given his previous pardons, perhaps not out of the question. Trump issued a blanket pardon for everyone who participated in the Jan. 6, 2021, Capitol riot. He also pardoned family: Charles Kushner, the father of Trump’s son-in-law Jared Kushner, was forgiven for tax evasion, illegal campaign contributions, and witness tampering.
And just this month, he pardoned rapper NBA YoungBoy on gun-related charges and reality TV couple Todd and Julie Chrisley, who were convicted of $30 million bank fraud.