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They both got their start as New York City-based moguls, and they both hosted popular 2000s reality shows in which they tormented ambitious strivers looking to climb the ladder of success.
So it should come as no surprise that Diddy and Donald Trump have known one another for quite some time.
But are the bonds from an old friendship enough to score a presidential pardon for the disgraced rapper?
We may soon find out.
Diddy performs onstage during the 2023 MTV Video Music Awards at Prudential Center on September 12, 2023 in Newark, New Jersey. (Photo by Noam Galai/Getty Images for MTV)
As you’ve no doubt heard by now, Diddy is currently in jail awaiting trial on sex trafficking and rape charges.
He was in court for a hearing last month, and witnesses say the months behind bars have taken an obvious toll.
Onlookers described Diddy as “bloated” and “grey-haired,” a shell of the exuberant entrepreneur who first made a name for himself way back in the early ’90s.
Diddy is due back in court for the start of his trial on May 5. And insiders say he’s hoping that his old pal the Donald will render the outcome moot by issuing a presidential pardon.
Sean ‘Diddy’ Combs attends the 2022 BET Awards at Microsoft Theater on June 26, 2022 in Los Angeles, California. (Photo by Amy Sussman/Getty Images)
“Donald was always invited to Diddy’s legendary parties,” journalist Rob Shuter told Radar Online this week. “They’ve known each other forever. Diddy admired Trump’s swagger – the bravado, the flash. He built part of his brand around that energy,” he continued, adding:
“Diddy thinks Donald owes him one. He’s counting on their history to keep him out of an orange jumpsuit.”
It might sound like a long shot — and it is — but the fact remains that Donald and Diddy go way back.
Diddy has sung Donald’s praises on numerous occasions, and Trump memorably described the rapper as “a good friend of mine” on an episode of The Apprentice.
U.S. President Donald Trump gestures while speaking during an executive order signing event in the Oval Office of the White House on March 31, 2025 in Washington, DC. (Photo by Andrew Harnik/Getty Images)
“I have to say, I am a very strict and focused businesswoman because working for Diddy for six years trained me to have to be perfect,” Aubrey O’Day — who competed on both men’s reality shows — told Trump.
“Working for Diddy?” Trump asked. “I love Diddy. … You know he is a good friend of mine. He’s a good guy. Is he a good guy?”
When O’Day declined to answer, Trump remarked:
“Oh well, I think he’s a good guy, I’m going to stick up for him.”
“He’s an idiot, a terrible judge of character, and a liar,” one X user wrote in response to the resurfaced clip
“Birds of a feather,” another added.
Trump might be willing to stick up for Diddy, but will he go so far as to issue him a presidential pardon? Hopefully Puff’s not holding his breath, as that seems exceedingly unlikely.
Diddy Preparing to ‘Beg’ Donald Trump For Presidential Pardon: Report was originally published on The Hollywood Gossip.
They both got their start as New York City-based moguls, and they both hosted popular 2000s reality shows in which they tormented ambitious strivers looking to climb the ladder of success.
So it should come as no surprise that Diddy and Donald Trump have known one another for quite some time.
But are the bonds from an old friendship enough to score a presidential pardon for the disgraced rapper?
We may soon find out.
Diddy performs onstage during the 2023 MTV Video Music Awards at Prudential Center on September 12, 2023 in Newark, New Jersey. (Photo by Noam Galai/Getty Images for MTV)
Diddy’s downfall
As you’ve no doubt heard by now, Diddy is currently in jail awaiting trial on sex trafficking and rape charges.
He was in court for a hearing last month, and witnesses say the months behind bars have taken an obvious toll.
Onlookers described Diddy as “bloated” and “grey-haired,” a shell of the exuberant entrepreneur who first made a name for himself way back in the early ’90s.
Diddy is due back in court for the start of his trial on May 5. And insiders say he’s hoping that his old pal the Donald will render the outcome moot by issuing a presidential pardon.
Sean ‘Diddy’ Combs attends the 2022 BET Awards at Microsoft Theater on June 26, 2022 in Los Angeles, California. (Photo by Amy Sussman/Getty Images)
“Donald was always invited to Diddy’s legendary parties,” journalist Rob Shuter told Radar Online this week. “They’ve known each other forever. Diddy admired Trump’s swagger – the bravado, the flash. He built part of his brand around that energy,” he continued, adding:
“Diddy thinks Donald owes him one. He’s counting on their history to keep him out of an orange jumpsuit.”
It might sound like a long shot — and it is — but the fact remains that Donald and Diddy go way back.
Donald and Diddy’s long history of mutual admiration
Diddy has sung Donald’s praises on numerous occasions, and Trump memorably described the rapper as “a good friend of mine” on an episode of The Apprentice.
U.S. President Donald Trump gestures while speaking during an executive order signing event in the Oval Office of the White House on March 31, 2025 in Washington, DC. (Photo by Andrew Harnik/Getty Images)
“I have to say, I am a very strict and focused businesswoman because working for Diddy for six years trained me to have to be perfect,” Aubrey O’Day — who competed on both men’s reality shows — told Trump.
“Working for Diddy?” Trump asked. “I love Diddy. … You know he is a good friend of mine. He’s a good guy. Is he a good guy?”
When O’Day declined to answer, Trump remarked:
“Oh well, I think he’s a good guy, I’m going to stick up for him.”
“He’s an idiot, a terrible judge of character, and a liar,” one X user wrote in response to the resurfaced clip
“Birds of a feather,” another added.
Trump might be willing to stick up for Diddy, but will he go so far as to issue him a presidential pardon? Hopefully Puff’s not holding his breath, as that seems exceedingly unlikely.
Diddy Preparing to ‘Beg’ Donald Trump For Presidential Pardon: Report was originally published on The Hollywood Gossip.