Sept. 2, 2005 - West declares, "George Bush doesn't care about Black people" in historic moment during A Concert for Hurricane Relief.
Following Hurricane Katrina in New Orleans, La., NBC hosted an hour-long, star-studded benefit concert titled A Concert for Hurricane Relief. The rapper stood side-by-side with comedian and actor Mike Myers when he veered off script and spoke from the heart about the disproportionate tragedies facing the Black community in the wake of the storm. "George Bush doesn't care about Black people," West said candidly, ultimately cutting his time on-screen short.
In 2010, former President Bush described West's outburst in an interview with Matt Lauer "one of the most disgusting moments in my presidency."
August 5, 2015 - The Wests takes a selfie with Senator Hillary Clinton during her 2016 presidential campaign fundraiser.
But first, lemme take a selfie! Kim Kardashian utilized her social media influence to endorse Sen. Hillary Clinton as the Democratic presidential candidate by snapping a picture with Clinton and West at one of her fundraisers.
Aug. 30, 2015 - He first announces his 2020 presidential run at the 2015 MTV VMAs.
When Taylor Swift presented the coveted Michael Jackson Video Vanguard Award to West at the 2015 MTV Video Music Awards, who famously interrupted her acceptance speech at the same awards show just six years prior, he took the stage for yet another viral moment. "And yes, as you probably could have guessed by this moment, I have decided, in 2020, to run for president," West declared at the end of his speech. Thus, #Kanye2020 was born.
And what did Trump have to say about his potential opponent? "He’s actually a different kind of person than people think. He’s a nice guy. I hope to run against him someday," he declared in an exclusive interview with Rolling Stone on Sept. 2, three days after West made the announcement.
Sept. 24, 2015 - West gives Vanity Fair an exclusive interview about his 2020 presidential run.
Following his on-stage stint at the MTV VMAs, the "Famous" rapper told Vanity Fair in an interview that he was "definitely" running for president in 2020 -- and he prefers "not to run against someone." "I would be like 'I want to work with you.' As soon as I heard [Ben] Carson speak, I tried for three weeks to get on the phone with him. I was like this is the most brilliant guy. And I think all the people running right now have something that each of the others needs," he said at the time.
When responding to fans' positive reactions to his announcement, the rapper said he thinks about what his time in office will look like while he's at the club. "I sit in clubs and I’m like, Wow, I’ve got five years before I go and run for office and I’ve got a lot of research to do, I’ve got a lot of growing up to do," he said.
November 17, 2016 -- He tells concertgoers that he didn't vote in the 2016 election but would've picked Trump during Saint Pablo Tour stop.
While performing at San Jose's SAP Center during his 2016 Saint Pablo Tour run, The Life of Pablo artist turned his iconic floating stage into a political platform. "I told y'all I didn't vote, right? But I didn't tell you.... But if I would've voted, I would've voted for Trump," he told the audience, who engaged in a mixed chorus of applause and booing.
He later specifically addressed Black people in his speech, saying, "Stop focusing on racism. This world is racist, okay?! Let's stop being distracted to focus on that as much. It's just a f---ing fact. We are in a racist country. Period!... And not one or the other candidate was going to instantly be able to change that because of they views."
West also outlined his views regarding education reform, women's rights, gay marriage, housing and immigration as well as his future campaign strategy in between songs.
December 13, 2016 - Trump meets with West at the rapper's request at Trump Tower in New York City.
After being hospitalized in LA from exhaustion and sleep deprivation, West met up with the president at Trump Tower in NYC. The two shared an awkward embrace in front of reporters asking the rapper if he still planned on running for president in 2020 and if he planned on performing at Trump's upcoming inauguration at the time. "I just want to take a picture right now," he replied with a grin. Trump told the surrounding press they've been friends for life and were simply discussing life that morning.
April 25, 2018 - West sporadically sounds off about Trump, Clinton and former President Barack Obama in political Twitter thread.
West and Trump don't just share their love for Twitter -- they also have "dragon energy" in common. According to a series of tweets from the "Lift Yourself" musician, West explained to his nearly 30 million Twitter followers that they can't convince him not to love Trump because he loves Clinton at the same time. "You don't have to agree with trump but the mob can't make me not love him. We are both dragon energy. He is my brother," West wrote at the time, introducing fans to his "free thought" ideology. "I love everyone. I don't agree with everything anyone does. That's what makes us individuals. And we have the right to independent thought.... I love Hilary too."
West's equivalent support for both 2016 presidential candidates stems from the fact that he doesn't align with either political party. "I'm not even political. I'm not a democrat or a republican," he wrote on Twitter. The Grammy award-winning singer also criticized Obama for not improving the conditions of their shared hometown of Chicago. Out of all the parties name-checked in the Twitter thread, Trump chimed in and wrote, "Thank you Kanye, very cool!" regarding the praise he received.
April 27, 2018 - West drops "Ye vs. the People" track featuring T.I. that defends Trump and backs himself up as a potential presidential candidate.
West hit the booth with T.I. to drop the politically charged song "Ye vs. the People" that outlines right in the first verse how he sees the presidential sequence going: "I know Obama was heaven-sent/ But ever since Trump won, it proved that I could be president." The back-and-forth between both rappers debate that all Black people don't have to identify as Democrats, West flipped the negative perception of "Make America Great America" on its head, and more over the Four Tops' "7 Rooms of Gloom" sample. "Ye vs. the People" debuted at No. 85 on the Billboard Hot 100 chart on May 8, 2018.
May 1, 2018 - West declares slavery "sounds like a choice" in controversial clip during TMZ newsroom outbreak.
West stopped by TMZ's office to share his unfiltered political opinions yet again with founder Harvey Levin and co-executive producer Charles Latibeaudiere. He said he "felt a freedom" wearing the red Make America Great Again hat in a since-deleted Twitter selfie with Universal Music Group CEO Lucian Grainge and 300 Entertainment CEO/co-founder Lyor Cohen. "I just love Trump, that's my boy!" West said.
While speaking as a representative of the larger Black community, the rapper made a controversial note about slavery. "When you hear about slavery for 400 years... for 400 years? That sounds like a choice," he told Levin and Latibeaudiere while chuckling during the "TMZ Live" interview.
September 30, 2018 -- West drops another MAGA hat selfie on Twitter.
"Make America Great Again had a negative perception/ I took it, wore it, rocked it, gave it a new direction/ Added empathy, care and love and affection/ And y'all simply questionin' my methods," West rapped on "Ye vs. the People." But he showed his listeners exactly what he meant with his MAGA hat selfie that represented "good and American becoming whole again."
Oct. 11, 2018 - West and Trump meet again, but this time, at the White House.
Their bromance keeps brewing in the highest places. West sat down with Trump in the Oval Office to discuss his wife's previous visit when she asked Trump to grant first-time nonviolent drug offender Alice Johnson clemency, his Yeezy partnership with Adidas, the murder rate in his Chicago hometown and how to improve local crime prevention, the 13th amendment, and the superpowers his MAGA hat gives him.
"You know, they tried to scare me to not wear this hat -- my own friends. But this hat, it gives me -- it gives me power, in a way," West told the president. "It was something about when I put this hat on, it made me feel like Superman. You made a Superman. That was my -- that’s my favorite superhero. And you made a Superman cape."
Bringing things full circle, West also addressed his 2005 remarks about former President Bush not caring about Black people, blaming how he was feeling and how he was programmed "to think from a victimized mentality. A welfare mentality."
April 15, 2020 - West reveals if and who he's voting for during the 2020 election in his GQ cover story.
While gracing the May cover of GQ and showing off his vision of the future, the Jesus Is King singer declared he would vote during this election while making fans guess whose name he would check on the ballot. "I'm definitely voting this time. And we know who I'm voting on," he said in the interview. "And I'm not going to be told by the people around me and the people that have their agenda that my career is going to be over. Because guess what: I'm still here! Jesus Is King was No. 1! I was told my career would end if I wasn't with her. What kind of campaign is that, anyway? That's like if Obama's campaign was 'I'm with black.' What's the point of being a celebrity if you can't have an opinion? Everybody make their own opinion! You know?"
July 4, 2020 - He officially announces he's running for president in the 2020 race via Twitter.
Fans might have thought West would be checking Trump's name on the ballot, but the "I Love Kanye" singer announced on the 4th of July this year that he plans on having his name on the 2020 presidential ticket -- without announcing which party he plans to run for. "We must now realize the promise of America by trusting God, unifying our vision and building our future. I am running for president of the United States! #2020VISION," the rapper-turned-political candidate wrote on Twitter.
Tesla/SpaceX CEO and his orange-wearing buddy Elon Musk is more than onboard with West's campaign, replying, "You have my full support!"