Inside Diddy's Deep State Entanglements: A Full Political Timeline

A detailed timeline of all of Sean "Diddy" Combs' political affiliations and endorsements from the last two decades

Jun 02, 2025

We’re four weeks into the federal trial of U.S. vs. Sean Combs, and the internet lit up after Donald Trump was asked if he’d consider pardoning Diddy.

50 Cent said “not so fast.”

He reminded his audience of all the times Diddy talked shit about Trump and said he was going to reach out to Trump and snitch to make sure a pardon is never on the table.

50 Cent isn’t wrong. There’s several times that Diddy was caught on camera trashing Trump, like the time he said “white men like Trump need to be banished.” But after digging through Diddy’s political history, one thing is clear: Trump wasn’t lying.
There was a time when Diddy liked him—at least, enough to be friendly.

So what changed?

When news of Diddy's arrest broke, writer Shane Cashman cleverly summed it up with his tweet: "Vote or Die Rapper Has Been Arrested," reminding everyone of Sean “Diddy” Combs’ long-standing role as Hollywood’s leading political mascot.

Since his federal indictment, photos of Diddy alongside famous politicians throughout the years have been used in a game of online tug-of war, both sides trying to use his downfall to their advantage.

Conservatives started digging up old photos of Diddy cozying up to Hillary Clinton and Barack Obama, framing him as a pawn of the liberal elite. Meanwhile, liberals posted snapshots of Diddy all dressed up at elite New York events next to Donald and Melania Trump.

Last fall, Marjorie Taylor Green shared a clip of Puff Daddy interviewing Barack Obama in 2004 on X with the caption: “Since P Diddy is trending, heres a video of Obama thanking “Puff Daddy.” Don’t share this video Barack and Michelle Obama will be very upset.”

The Jimmy Kimmel Live! staff clapped back at conservative talking heads and aired a rare clip from a 2005 episode of the Celebrity Apprentice where Trump calls Diddy a “good guy.”

Even Kamala Harris couldn’t escape a Diddy association. A 2020 tweet thanking Diddy for his support during the pandemic resurfaced and went viral. She wasn’t free from the jokes that followed either, some calling her his “baby oil plug.”

The only person who managed to escape a Diddy snapshot was Joe Biden.

I always assumed Diddy was a diehard Democrat but after seeing all this conflicting information online, his political stance became just as muddy to me as his secret stash of baby oil.

I couldn't help but wonder if the Johnson and Johnson baby oil was linked to the Johnson and Johnson vaccine but instead of losing myself down this rabbit hole, I spend a week exploring Diddy’s political history to see if there’s any depth behind these affiliations.

Is Diddy a deep state pawn or was his career-long political agenda financially motivated? Let’s see.

Timeline of Diddy’s Political Connections

Puff Daddy Shaking Hands with Donald Trump, 1997

In 1997, when Diddy still went by the name “Puff Daddy,” he was photographed brushing shoulders with Donald Trump and other influential businessmen at high-profile events in New York.

"I spend absurd money, private bird money / That Bill Gates, Donald Trump, Bloomberg money (you know what it is,” Diddy rapped in his 2006 song “We Gon’ Make It,” boasting about having the same amount of wealth as Trump.

Puff Daddy Launches Vote or Die! Campaign, 2004

I always knew Puff Daddy was the official poster boy for “Vote or Die!,” but until now, I wasn’t aware that he launched this campaign himself through his organization, Citizen Change, founded to empower and educate young voters.

With the Bush vs. Kerry presidential election around the corner, he set out on a mission to get more young voters out to the polls, styling other famous pop icons in matching bold-faced t-shirts to help blow up the cause.

Coordinating the marketing strategies behind the scenes was Democrat Alexis McGill, the current CEO of Planned Parenthood, who served as the Executive Director of Citizen Change at the time.

While Puff Daddy never endorsed a candidate publicly during this campaign, a conservative organization filed a complaint against him in November 2005, claiming that he violated election law by promoting Kerry and opposing Bush. The group said public record backs its claim that Combs and Citizen Change “undertook a campaign to defeat Mr. Bush and elect the Democratic nominee.”

The complaint cited "Vote or Die!" rallies sponsored by Citizen Change in which actor Leonardo DiCaprio urged the crowd to back Kerry.

Even though Kerry ended up losing the election, given McGill’s major role at the organization and the support the campaign received from left-leaning television networks, it’s no wonder that a conservative organization suspected the campaign was funded by the left.

When it came to Democratic votes, the youth vote was the only demographic who gave John Kerry the win. John Kerry got 54 percent, compared to Bush's 44 percent. (In 2000, Al Gore got 48 percent, Bush 46 percent.)

Diddy was disappointed at the media’s coverage of the campaign outcome who he believed weren’t applauding his efforts enough. Newscasters pointed out that the hip-hop mogul’s movement only increased young voter turnout by 4.6 million votes.

"Is it a conspiracy?" Diddy asked. “That increase should have been applauded, you know what I mean? We got knocked down so much for being irresponsible, for people trying to say that this generation is irresponsible, that this generation doesn't care, that this generation isn't interested in things that are serious. Then, something like this happens -- 4 million or so more votes, like bam! -- and what are folks saying? Young black and Latino kids are voting for the first time, and what are folks saying? I'm not being defensive. I know the truth.”

"I'm just calling it as it is,” he said.

Alexis McGill was a speaker at the 2024 Democratic National Convention.

Diddy Brings Vote or Die! Movement to 2004 DNC

“We’re spreading a simple, urgent message: vote or die! Yes, it’s that serious. They used to joke around about us about saying we were disenfranchised, saying we’re too lazy to vote. On November 3rd, they won’t be laughing no more. The youth of America will have the last laugh!” - Diddy at the 2004 DNC

Donald and Melania Trump with Diddy at a Vote or Die! Art Exhibit, 2004

In 2004, Trump was a registered Democrat. He didn’t change his party affiliation to Republican until 2009. He went independent in 2011 and returned to the Republican Party in 2012.

Puff Daddy Interviews Barack Obama and Hillary Clinton, 2004

Does it get any more quintessentially 2000s than this? A young Puff Daddy, decked out in his iconic “Vote or Die” tee, holding an MTV News mic as he interviews a then-unknown Illinois senator named Barack Obama—four years before he would become president. It’s the ultimate snapshot of a time when celebs used their influence to drive political engagement, a strategy Obama openly supported in this interview, telling Puff Daddy how important his voice is for young people in America.

“You’re a motivating force for young people all across the country,” Obama tells him.

“Your music moves people. You’re a trendsetter,” he says. But part of what we want to do is to make sure that we’re setting a trend in terms of political participation.”

Diddy paid Hillary Clinton a strong compliment during her MTV News interview for Vote or Die!

“You’re one of the few politicians that young people relate to,” Diddy told Clinton.

Clinton stresses the importance of voting to avoid a future filled with homelessness, unemployment and violence, a fitting description of modern times.

Below is a photo of Diddy hugging Clinton at the 2004 DNC.

Trump Says “I Love Diddy in Celebrity Apprentice Clip, 2005

The 2005 Celebrity Apprentice clip that resurfaced on Jimmy Kimmel Live! shows a scene where a young red-headed Aubrey O’Day is pitching herself to Donald Trump. She tells him that working for Diddy for six years made her a perfectionist.

Trump asks her if Diddy is a good guy but before letting her answer, answers the question himself and says, “I think he’s a good guy. I’m going to stick up for him.”

Now a decade later later, Aubrey O’Day has become known as one of the first celebrities who took a public stance against Diddy, calling him out for his abusive behavior and showing her support to other victims.

Diddy Endorses Barack Obama, 2008

Diddy and Bill Clinton Together at Haiti Relief Benefit, 2010

President Clinton flew to Miami for the “SOS Saving Ourselves- Help for Haiti” fundraiser, brought to you by Procter & Gamble and Pepsi, hosted by Diddy, Pharrell and Queen Latifah. (Pharrell was also a model for Diddy’s Vote or Die! campaign)

“To add to the already stellar lineup, President Clinton lends his time and inspiration, as he will arrive directly from supporting the relief efforts in Haiti with The Clinton Foundation Haiti Fund.”

Diddy Calls Trump a “Friend” in 2015

Diddy didn’t always hate Donald Trump. In an interview with The Washington Post in October 2015, he called him a “friend.”

"Donald Trump is a friend of mine, and he works very hard," he said.

Diddy Criticizes Barack Obama and Hillary Clinton, 2016

During a 2016 appearance on MSNBC, Diddy criticized Barack Obama for not doing enough for the black community. Diddy stresses the importance of the black vote and said he believes the black vote is what got Obama elected in the first place.

“We put President Obama in the White House, and when I look back I just wanted more done for my people,” he said.

“I think it’s time to turn up the heat. The black vote is going to decide who the next president is of the United States.”

He also criticized Hillary Clinton and told the black community to “hold their votes” until Clinton addresses their community directly.

“Hillary Clinton, you know, I hope she starts to talk directly to the black community. It really makes me feel, you know, almost hurt that our issues are not addressed and we’re such a big part of the voting block,” he said.

Diddy Sits Down With Obama, 2017

Just a year after he criticized Obama on MSNBC, Diddy shared a photo of himself sitting in a room with the former president to his Facebook with the caption:

“This week was a great week. Shout out to the king Barack Obama!!! #BlackExcellence.”

The post is still live, here.

Kamala’s Tweet Thanking Diddy, April 2020

“Thank you Diddy for hosting this town hall last night. There’s a lot at stake for our communities right now and it’s critical we bring to the forefront how coronavirus is perpetuating racial inequality and health disparties,” Kamala Harris tweeted April 10, 2020.

Diddy Endorses Joe Biden, October 2020

Diddy received a lot of criticism for criticizing Hillary Clinton and telling black voters to “hold their votes.” But his tune changed completely in late October 2020, when he sat down with Charlamagne the God on Black News, just weeks before the election to fully endorse Joe Biden.

“The NUMBER ONE priority is to get Trump out of office. HE HAS TO GO. We can’t allow this man to continue to try and DIVIDE US,” he said vocalizing his sudden hatred for Trump publicly.

The 35-minute interview served one obvious purpose: to sway viewers to vote for Biden using fear-mongering tactics. Diddy warned his community that a dangerous race war could erupt if Trump is reelected.

“The number one people who should be scared to death of this man is white people. If this man is elected, we’re not standing by no more and getting killed. We aren’t scared of anybody standing up and standing by. We’re on the verge of a race war,” he said.

“White men like Trump need to be banished,”

-Sean Combs, October 2020

Diddy Launches His Own Political Party “Our Black Party”

Diddy used this interview to launch his own political party, “Our Black Party” to help further the black agenda.

“The No. 1 goal is to unify behind a Black agenda,” he told Charlamagne The God.

Our Black Party’s 2020 primary goal was solely to get President Trump out of office.

Donald Trump Jr’s Connection to the Late Kim Porter, 2018

On a April 2024 episode of Akademiks' podcast, Donald Trump Jr. revealed a personal anecdote involving the late Kim Porter, the longtime on-again, off-again partner of Diddy, who passed away unexpectedly in 2018. Porter, a model and mother of three of Diddy's children, was a fixture in the same social circles as Trump Jr.’s ex-wife, Vanessa Haydon. Both women modeled in New York during the 90s and became friends.

Porter’s sudden death at 47, reportedly due to pneumonia, left many in shock. When Porter’s death was ruled “natural,” Trump Jr. remembers Haydon being skeptical.

“When that happened, she called me….something is up with that she said,” Jr. recalls.

“Maybe it’s natural, but not a lot of people die at 47 of pneumonia,” he said before pointing out that Porter was also in good shape.

Trump Jr. said Porter would confide in Haydon about her relationship with Diddy and he remembers there being a lot of “weird shit.”

“She was really afraid of him,” Jr. said. “She was sort of always in fear of something happening.”

When the conversation turned to Diddy’s relationship with Cassie, Jr. was quick to clarify that he wasn’t trying to spread rumors but simply recounting what his ex-wife (who knew Porter well) had shared with him.

In this episode, Jr. also acknowledges that his father’s relationship with Diddy has changed throughout the years.

“I know him and your father must have had relationships,” Akademiks says referring to Donald Trump and Diddy.

“They did for a long time and then he went full leftist because maybe of some of the stuff he’s been doing. That whole thing’s crazy,” Jr. replies.

Diddy Returns The Key to the City of New York, 2024

After the disturbing video of Diddy assaulting his ex-girlfriend Cassie surfaced last spring, New York Mayor Eric Adams wrote Sean “Diddy” Combs a formal letter asking for him to turn in the “The Key to the City of New York.”

Jesse Waters’ Opinion on Diddy’s Role In Politics

Fox News Anchor Jesse Waters weighed in on Diddy’s role in American politics.

“Democrats used his charisma, star power and street cred in the Black community every single election. For Diddy, this was a business opportunity. He was blessed by the professional class and commercialized. He was in the back pocket of the powerful and that made him powerful with a free pass. He was so loved that New York City Mayor Eric Adams handed him the key to the city. ... Diddy didn't just have the key to the city. He had the key to the country. He endorsed the Democrats, politicked for them and got souls to the polls, as they say, but there was more to it than that. He was a political enforcer.” —Jesse Waters, 2024

After an afternoon of sifting through Diddy’s political history, one fact is indisputable: his public allegiance to the Democrats never faltered, no matter how many times he was photographed with Trump in a pinstripe suit.