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Donald Trump loves demonstrating his presidential power and inserting himself into celebrity drama. So despite the fact that Sean “Diddy” Combs is facing many horrific allegations and his federal racketeering and sex-trafficking trial is ongoing, there’s long been speculation that Trump will issue a pardon. And now, Trump has said he’s open to helping out Diddy, whom he once called a “good friend.”
So, will Trump pardon Diddy ? Can he even do that? What’s the history of their friendship? How is 50 Cent involved in all this? Here’s a guide, which we’ll keep updated, to the role Trump might play in the Diddy legal saga.
Can Trump pardon Diddy?
Yes. Article II, Section 2, of the Constitution gives the president the power to “grant Reprieves and Pardons for Offences against the United States, except in Cases of Impeachment.” Federal prosecutors in the Southern District of New York have charged Combs with five criminal counts, as NBC News summarized:
[Diddy faces] one count of racketeering conspiracy, which carries a maximum sentence of life in prison; two counts of sex trafficking by force, fraud or coercion, which carries a maximum sentence of life in prison and a mandatory minimum sentence of 15 years in prison; and two counts transportation to engage in prostitution, which carries a maximum sentence of 10 years in prison.
Combs has pleaded not guilty to all charges.
Diddy is also facing dozens of civil suits, but those are separate from the federal criminal trial and Trump can’t issue a pardon in those cases.
Did Trump say he would pardon Diddy?
Trump said he’d consider it, though he claims no one has asked him to do so.
A reporter asked Trump if he would pardon Diddy during a May 30 news conference in the Oval Office. Trump responded:
Nobody’s asked but I know people are thinking about it. I know they’re thinking about it. 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, although it’s certainly getting a lot of coverage.
I haven’t seen him, I haven’t spoken to him in years. He used to really like me a lot, but I think when I ran for politics he sort of, that relationship busted up from what I read. I don’t know. He didn’t tell me that, but I’d read some nasty statements in the paper all of a sudden.
… So, I don’t know. I would certainly look at the facts. if I think somebody was mistreated, whether they like me or don’t like me it wouldn’t have any impact.
Why would Trump even consider pardoning Diddy?
Diddy’s close associates have been cozying up to the Trump administration in the hopes of securing a pardon, according to a May 16 Rolling Stone report:
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.
It does not sound like Combs associates have made much progress on this front. The report notes that the small number of top Trump officials who have been privy to these efforts “have expressed deep reservations” about a pardon, and there’s “no evidence that Trump is personally aware of any of theses conversations.”
On the other hand, it does seem like something Trump would do. The president has been on a pardoning spree in recent weeks, sparing a MAGA-aligned sheriff convicted of bribery, a donor’s son found guilty of tax crimes, and a pair of reality-TV stars convicted of tax evasion (not to mention 1,500 January 6 rioters). In a recent interview, former Death Row Records CEO Suge Knight, who is in prison for voluntary manslaughter, suggested that Diddy will be fine because “if he gets convicted, Trump’s going to pardon him.” And an Onion headline joked, “Sean Combs Asks for Quick Trial So He Can Get to Part Where Trump Pardons Him.”
What is 50 Cent’s role in all this?
The rapper is a longtime Diddy foe, and he’s currently co-producing a Netflix docuseries about the abuse allegations against Diddy. In a series of Instagram posts, 50 Cent suggested he’s going to try to convince Trump not to issue a pardon.
“He said some really bad things about Trump, it’s not ok. Im gonna reach out so he knows how I feel about this guy,” 50 Cent said in the first post on June 1, which has now been deleted.
In another deleted post he wrote, “Donald doesn’t take well to disrespect, and doesn’t forget who chooses to go against him. while working tirelessly to make America great again there is no room for distraction. He would consider pardoning anyone who was being mistreated not Puffy Daddy.”
Later 50 Cent clarified that he isn’t looking to “nuke” Diddy’s pardon chances, he just wants to “make sure Trump is aware.”
On June 2, 50 Cent followed up by posting two old clips of Diddy insulting Trump.
Are Trump and Diddy friends?
Yes, they were friends for many years, though as the president noted while talking to reporters in the Oval Office, it seems Combs soured on Trump once he entered politics.
Its unclear if Trump and Diddy were bosom buddies, or just “friends” in the sense that they were two reality-TV celebrities who ran in the same circles in the late ’90s and early ’00s. But we do know that they publicly discussed their friendship on several occasions, praised each other’s business skills, and were photographed together at many events.
A 1999 Vibe piece written by Nancy Jo Sales about Trump’s relationship with the hip-hop community noted that he was the first to show up to Diddy’s birthday party, and that then-17-year-old Ivanka was impressed that her dad knew such a cool celebrity. “I think Puff Daddy is a great guy,” Trump said.
During a 2012 episode of The Celebrity Apprentice, Trump told contestant Aubry O’Day, who had worked for Diddy, that he was a friend.
“I love Diddy. You know he’s a good friend of mine, he’s a good guy,” Trump said. He then asked O’Day, “Is he a good guy?” and she said she didn’t want to answer. (Years later, the singer accused Diddy of “grooming” and said she was kicked out of the girl group he created, Danity Kane, for not doing “what was expected” of her — “not talent wise but in other areas.”)
“I think he’s a good guy, I’m going to stick up for him,” Trump said.
Diddy referred to Trump in his 2006 hit “We Gon’ Make It,” rapping, “I spend absurd money, private bird money / That Bill Gates, Donald Trump, Bloomberg money (you know what it is).”
In 2015, months after Trump launched his presidential campaign, Diddy told the Washington Post, “Donald Trump is a friend of mine, and he works very hard.”
So is Diddy a Trump campaign supporter?
If he was, he isn’t anymore. A month before the 2016 election, Combs was still calling Trump a friend, but he wouldn’t commit to voting for him in an interview with the New York Post:
“I always liked Donald’s style,” says Combs. “I do have a tie he gifted me. I wear it.
“As far as voting for him, that has yet to be seen.”
When asked what he thought about the Trump presidency in 2017, Diddy told the Daily Beast:
“I think that to be honest, we don’t really give a f*** about Trump, because [black people are] in the same f*****-up position. So that’s not what we’re on. The tomfoolery that’s going on in D.C., that’s just regular everyday business to black folks. That’s not surprising,” he said.
By 2020, Diddy had fully turned against Trump. In an interview with Charlamagne tha God, he said, “White men like Trump need to be banished. That way of thinking is real dangerous.”
He then endorsed Joe Biden, saying, “When you look at it, we don’t have no choice. Say what you want about Biden, I can’t say I love the pick either. But we’ve got to get him in office, and then we’ve got to hold him accountable.”
The Feds raided Diddy’s mansions in March 2024 and he was indicted in September 2024, so no one was interested in his take on the 2024 presidential election (though Trump and his supporters made several attempts to smear Kamala Harris by falsely linking her to the allegations against Diddy).
What’s happened in the Diddy trial so far?
Jury selection began on May 5, and opening arguments started on May 12.
The first witness to testify was singer Casandra “Cassie” Ventura, Diddy’s ex-girlfriend, who accused him of years of physical, emotional, and sexual abuse. She said Diddy routinely forced her an others to participate in “freak offs,” multi-day marathons of sex and drug use that he orchestrated. The defense has acknowledged that Diddy’s relationship with Ventura was plagued by drug abuse and domestic violence, but claimed that consensual relationships are being misconstrued as sex trafficking.
Jurors have heard from several other people who say they witnessed and were subjected to Combs’s alleged abuse and violent behavior, including Danity Kane member Dawn Richard, Cassie’s friends and family members, and several former Diddy employees. Rapper Kid Cudi testified that Diddy broke into his home after discovering he was dating Cassie, and said he suspected that Diddy was behind the firebombing of his car. A former assistant using the pseudonym “Mia” accused Diddy of raping and assaulting her. Cassie’s friend Bryana Bongolan testified that the mogul once dangled her over the railing of an 17th-floor apartment balcony and told her “I could kill you.”
Click here for Vulture’s full coverage of the Diddy trial.
When will the Diddy trial end?
The defense is expected to make its case in mid-June. Judge Arun Subramanian said the trial should wrap up by July 4. So Trump has at least a few more weeks to “look at what’s happening” and decide whether he should intervene if Diddy is convicted.
