It’s one of the weirdest "friendships" in pop culture history. One day they're hitting the Hamptons together, and the next, there are calls for "banishment." If you’re trying to figure out what did diddy say about trump, you have to look at a timeline that spans decades, moving from genuine admiration to public political warfare, and finally, to the desperate plea for a pardon that’s currently dominating the 2026 news cycle.
Honestly, it wasn't always this messy. Back in the 90s and early 2000s, Sean "Diddy" Combs and Donald Trump were basically two peas in a pod—moguls who loved the spotlight, expensive suits, and being seen at the hottest parties. But as the political climate shifted, so did the rhetoric.
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The Early Years: "I Love Diddy"
Before the rallies and the indictments, there was just the glitz. Trump and Diddy were frequently photographed together at fashion shows, charity galas, and launch parties. Trump didn't just tolerate Diddy; he openly praised him.
In a now-infamous 2012 clip from The Celebrity Apprentice, Trump went to bat for the Bad Boy mogul. When contestant Aubrey O'Day—who had her own complicated history with Diddy in the group Danity Kane—tried to dodge a question about him, Trump didn't hold back. "I love Diddy," Trump said. "You know he’s a good friend of mine, he’s a good guy." He even doubled down, saying he was going to "stick up for him" because he viewed him as a peer in the world of high-stakes business.
Diddy, for his part, was equally complimentary during this era. He saw Trump as a blueprint for success. They were both masters of branding. They both put their names on everything from buildings to vodka. At the time, Diddy’s comments about Trump were mostly centered on business respect.
The 2016 Shift: From Friends to "Fear"
Everything changed when Trump traded the boardroom for the campaign trail. While Diddy didn't immediately go on the attack, his tone became noticeably more cautious. By late 2016, Diddy was using his platform to push the "Vote or Die" narrative again, but this time with a sharp edge toward the Republican candidate.
He told Rev. Al Sharpton in an MSNBC interview that the next president needed to focus on the "marginalized." He wasn't calling Trump a "good guy" anymore. Instead, he was questioning whether the billionaire he used to party with actually understood the needs of the Black community.
2020: The "Banishment" Comments
If the relationship was strained in 2016, it completely imploded by 2020. This is where the most viral quotes about what did diddy say about trump come from. During a conversation with Charlamagne Tha God on Revolt TV, Diddy didn't mince words.
"White men like Trump need to be banished. That way of thinking is real dangerous. This man literally threatened the lives of us and our families about going to vote."
He didn't stop there. He launched "Our Black Party" and officially endorsed Joe Biden. He told his followers that the "number one priority" was to get Trump out of office, claiming the country was on the "verge of a race war" because of Trump’s rhetoric. It was a 180-degree turn from the 2012 "good friend" days.
The Current 2026 Legal Drama: The Pardon Request
Fast forward to today. Diddy is currently serving a four-year sentence following his 2025 conviction on prostitution-related charges. In a move that shocked many—given his previous "banishment" comments—Diddy has reached out to the now-President Trump for clemency.
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Just this month, in January 2026, reports surfaced that Diddy sent a formal letter to the Oval Office asking for a pardon. Trump’s reaction? It’s complicated. In a recent interview with The New York Times, Trump confirmed he received the letter but isn't exactly rushing to sign it.
Trump told reporters, "He asked me for a pardon… through a letter." But he also pointed out that their relationship "soured" after Diddy’s public attacks. He even told Newsmax that while he once thought Diddy was "sort of half-innocent," the "nasty statements" Diddy made during the 2020 election make a pardon "more difficult."
Why This Matters Right Now
The reason everyone is Googling this is because it highlights the transactional nature of celebrity and politics. Diddy’s legal team is trying to leverage a decades-old friendship to bypass a prison sentence, while Trump is weighing his personal feelings against the political optics of pardoning a figure as controversial as Sean Combs.
If you’re following this story, here is what you need to keep an eye on:
- The Newsmax Interview: Trump’s comments here suggest that loyalty is his primary currency. Since Diddy "broke" that loyalty in 2020, his chances of a pardon look slim.
- The Legal Precedent: Legal experts are watching to see if Trump will use his pardon power for someone who was once a personal friend, even if they became a political enemy.
- Public Perception: For Diddy, the flip-flop from "banish him" to "please save me" has hurt his remaining credibility with his former political allies.
What to do next
To stay ahead of this evolving story, you should regularly check the Federal Bureau of Prisons locator to see if there are any changes in Diddy’s status, which would be the first sign of a granted petition. Additionally, keep an eye on official White House press releases regarding "Executive Grant of Clemency," as these are usually posted in batches during holiday weekends or at the end of a term. If you’re interested in the legal side, following the PACER (Public Access to Court Electronic Records) updates for the Southern District of New York will give you the most accurate info on his current appeals process.