Earlier this week, The Onion ran a piece headlined “Sean Combs Asks for Quick Trial So He Can Get to Part Where Trump Pardons Him.”
It may be on to something.
Combs, who was charged last September, is currently on trial in the Southern District of New York on sex-trafficking and racketeering conspiracy charges. But starting after Donald Trump won the presidential election in November, close associates of the mogul got to work on cozying up to Trumpland.
During the presidential transition and in the opening months of Trump’s second administration, several longtime friends and allies of Combs, who’ve known the rapper for many years, began reaching out to some Trump transition and administration officials, as well as to others close to the president, two sources familiar with the matter and another person briefed on it tell Rolling Stone. (The sources spoke on the condition of anonymity due to the sensitivity of the situation and on the condition that Rolling Stone not name certain individuals involved with these secret talks.)
“He’s willing to do anything to get out of jail,” a source who has known Combs for a decade tells Rolling Stone. “He’s always been this way. He’s always going to do what he has to do to get out of a situation.”
“He doesn’t even like Donald Trump,” they add.
The sources describe the conversations as ongoing and preliminary, with one of the people familiar with the matter characterizing it as Diddy World “making connections with the Trump team.” (A spokesperson for Combs did not return Rolling Stone’s request for comment, nor did the White House.)
To those on both sides of these conversations, the point is obvious: People who’ve known the rapper-producer for years are ingratiating themselves to individuals who have the president’s ear — in the hopes that this lays the groundwork and sets up senior-level lines of communication if Team Combs needs to plead for a pardon or commutation. There’s no evidence that Trump is personally aware of any of these conversations, and the president has not publicly weighed in on Combs’ criminal charges or prosecution. But the small number of senior Trump officials who are aware of it have expressed deep reservations about commuting a possible Combs sentence, given the severity of the charges.
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One of Combs’ close associates has some experience with presidential pardons and commutations. Corey Jacobs, a senior adviser to Combs and a trusted friend from his teenage years, walked free from prison when then-President Barack Obama granted him clemency in December 2016. He had been serving a life sentence for drug charges.
Combs has his life on the line, too, and he’s desperate to be released from the notorious Metropolitan Detention Center in Brooklyn. He’s moved for a speedy trial, turned down a plea deal, and pleaded not guilty to the five federal counts against him. If convicted, the mogul faces 15 years to life in prison.
During the private outreach to members of Trump’s government and social orbit, Combs’ allies have tried to paint the rapper’s prosecution in decidedly Trumpian terms, playing to the Republican vision of the president as a martyr and perennial victim. In their telling, he and Trump are both successful businessmen and controversial celebrities who have been unfairly targeted by the feds and prosecutors in the Southern District of New York — and they have each had to deal with a barrage of sexual-assault allegations that each insists are false.
“The words ‘deep state’ came up once or twice,” says one of the sources familiar with the outreach.
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“This case is about Sean Combs’ private, personal sex life, which has nothing to do with his lawful businesses,” Combs’ attorney, Teny Geragos, said during the defense’s opening statements on Monday. “The government has no place here in this man’s private bedrooms.”
The Combs supporters have also reminded administration officials — including some who are involved in clemency considerations at the Trump White House — and their other MAGAworld contacts that the president and rapper and fellow mogul have known each other for many years, and that Trump has publicly vouched for Combs’ character. In a now-widely circulated 2012 clip from Trump’s NBC reality-TV show, Celebrity Apprentice, Trump refers to the recording artist and producer as his “friend.”
“I love Diddy,” Trump says in the Apprentice episode. “You know he’s a good friend of mine; he’s a good guy,” he adds, before asking contestant — and a former artist for Combs — Aubrey O’Day, a singer in Danity Kane: “Is he a good guy?”
“I don’t want to answer that question,” she responded, to which the future president said that he’s “going to stick up for him,” anyway. (For years, O’Day alluded to alleged Combs misconduct. “The answer to what happens if you don’t do what the executives want? I’m the full-blown fucking story of that.” On Instagram, O’Day hinted that she will testify at Combs’ trial in the coming weeks.)
Combs has similarly been an outward fan of Trump’s. Over the years, the real-estate magnate has been spotted at a number of Combs’ VIP parties and events in New York City, including the Bad Boy founder’s blowout birthday bashes. On Combs’ 2006 track “We Gon’ Make It,” Combs name-drops his fellow mogul. “I spend absurd money, private bird money/That Bill Gates, Donald Trump, Bloomberg money,” Combs raps.
In 2015, months after Trump launched his presidential campaign, Combs told The Washington Post, “Donald Trump is a friend of mine, and he works very hard.” Two months before Trump’s 2016 victory, the rapper said on MSNBC, “I think [Black communities] got a little bit shortchanged” during Obama’s presidency, though he added that Obama did “an excellent job.”
Some of the Trump administration officials who are aware of the outreach don’t seem to be taking it seriously. They say that even with Trump and Combs’ preexisting relationship, it would be an uphill battle — and a public-relations nightmare for the White House — for Combs to win clemency given the nature of the alleged crimes, including allegedly sex-trafficking two ex-girlfriends as recently as 2024, two of the sources familiar with the situation say.
However, Trump has proven himself time and time again to be highly transactional when it comes to using the American presidency to do favors for powerful, rich friends and fellow celebrities.
Sometimes, a Trump pardon or commutation can be made — or broken — for the absolute pettiest of reasons. In the final moments of his first presidency, Trump granted clemency to rapper Snoop Dogg’s close friend and Death Row Records figure Michael “Harry-O” Harris. As Rolling Stone revealed early last year, the efforts to secure clemency were almost blown up by a furious Trump when the outgoing president was led to believe that Snoop Dogg still hated him. (Trump relented after Harris allies scrambled to show Trump documentary footage demonstrating that Snoop no longer loathed him.)
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At the end of his first administration, in the shadow of the deadly Jan. 6 Capitol riot and at the height of the coronavirus crisis, Trump also granted clemency to rapper Lil Wayne, in part because he thought the rapper was nice to him and, by Trump’s estimation, a political supporter.
After Rolling Stone published a recent cover story on Lil Wayne — in which the rap artist makes several candid comments about his interaction with Trump — multiple former officials in the first Trump White House complained to this magazine that Lil Wayne seemed ungrateful, and that he had played Trump and his advisers, like Trump son-in-law Jared Kushner, into helping him.
