scorecardInside Donald Trump and Kanye West's unlikely friendship
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Inside Donald Trump and Kanye West's unlikely friendship

Debanjali Bose   

Inside Donald Trump and Kanye West's unlikely friendship
Calla Kessler/The Washington Post/Getty Images
  • On the Fourth of July, Kanye West announced he's running for president in 2020.
  • West has enjoyed an unlikely — and public — friendship with President Trump since before the latter entered the Oval Office.
  • West's relationship with Trump is much more cordial than his relationships with former presidents George W. Bush and Barack Obama.
  • The White House and Kanye West's representatives didn't immediately respond to Business Insider's request for comment for this article.

Rapper and newly minted billionaire Kanye West celebrated the Fourth of July by tweeting out his 2020 bid for president. Tesla CEO Elon Musk and his wife Kim Kardashian West each sent support tweets.

While the feasibility of this bid is up for debate, West has enjoyed a very public friendship with the current occupant of the White House over the years.

"One of the main reasons I wore the red hat as a protest to the segregation of votes in the Black community. Also, other than the fact that I like Trump hotels and the saxophones in the lobby," West told Forbes in July 2020.

In the same Forbes interview, West added that he was "taking the red hat off" and that Trump was losing his support because "it looks like one big mess," specifically alluding to reports of Trump hiding inside a bunker during the Black Lives Matter protests in May. Trump has maintained that he was inspecting the bunker. West limited his criticism of Trump to those few points.

Here's a look inside West and Donald Trump's camaraderie over the years.

In 2009, Kanye West interrupted Taylor Swift's MTV Video Music Awards acceptance speech. Donald Trump called the move "disgusting."

In 2009, Kanye West interrupted Taylor Swift
West and Swift at the 2009 VMAs.      Jason DeCrow/AP Photo

Swift beat Beyoncé to win an award for "You Belong With Me" in the Best Female Video category. Unhappy with the results, West went onstage and said "Yo Taylor, I'm really happy for you, I'll let you finish, but Beyoncé has one of the best videos of all time. One of the best videos of all time!" leaving Swift and the audience perplexed.

The next day, Trump spoke to TMZ and said, "He couldn't care less about Beyonce. It was grandstanding to get attention." He added that he wanted to "boycott" West to avoid a repeat of the incident.

The White House and West's representatives did not respond to Business Insider's request for comment on Trump's comments about the incident.

Trump's feelings towards West seemed to have changed by 2014 when, during an appearance on Mario Lopez's "Extra," he complimented West and Kim Kardashian on their upcoming wedding.

Trump
Kim Kardashian and Kanye West at the 2019 Met Gala.      Angela Weiss/AFP/Getty Images

West and Kardashian West got married in a lavish ceremony in Florence, Italy, in May 2014. While the couple kept the TV cameras out of the actual ceremony, a good chunk of the days leading up to the event were televised for "Keeping Up With The Kardashians."

In early May, Trump told actor and TV host Mario Lopez that he knew the couple "well" and thought they were both "very nice people." He said he "wished them the best of luck" and that he hoped "they do well."

A year later, West won the Video Vanguard Award during the 2015 MTV VMAs. He shared plans to run for president in 2020 during his 13-minute long acceptance speech. Trump called his speech and declaration "interesting."

A year later, West won the Video Vanguard Award during the 2015 MTV VMAs. He shared plans to run for president in 2020 during his 13-minute long acceptance speech. Trump called his speech and declaration "interesting."
Kanye West accepts the Video Vanguard Award onstage during the 2015 MTV Video Music Awards.      Jeff Kravitz/MTV1415/FilmMagic

During his August 2015 VMA acceptance speech, West said, "It's not about me. It's about ideas. New ideas. People with ideas. People who believe in truth. And yes, as you probably could've guessed by this moment, I have decided in 2020 to run for President."

This took place roughly two months after Trump had announced his bid for the Republican nomination for the 2016 Presidential election.

At the time, Rolling Stone's Lauren Kelly asked Trump about West's sweeping VMAs speech and announcement, to which he responded that "he's a nice guy" and that he hopes to run against him someday.

West says he did not vote in the 2016 presidential elections but if he had, he would have chosen Trump over Hillary Clinton.

West says he did not vote in the 2016 presidential elections but if he had, he would have chosen Trump over Hillary Clinton.
Hillary Clinton and Donald Trump.      AP

"I told y'all I didn't vote, right? But if I would've voted, I would've voted for Trump," West told concert goers in California in November 2016. The audience did not hold back from booing him.

Kanye's announcement was in stark contrast to his wife's political opinions.

I got my selfie!!! I really loved hearing her speak & hearing her goals for our country! #HillaryForPresident

A post shared by Kim Kardashian West (@kimkardashian) on Aug 6, 2015 at 8:40pm PDT

 

In September 2016, Kardashian West announced she would be voting for Hillary Clinton.

She had previously shared that a conversation with Caitlyn Jenner — who is a Republican and supported Trump in the 2016 election — had left her undecided on who to vote for. She said Jenner had encouraged her to research which candidate aligned more closely with her political beliefs. 

The couple posed for a selfie with Clinton in August 2016.

West visited Trump Tower for a meeting with the president-elect in December 2016.

West visited Trump Tower for a meeting with the president-elect in December 2016.
West and Trump at Trump Tower in New York City in 2016.      AP Photo/Seth Wenig

West arrived in Trump Tower at a little after 9 a.m. and told reporters they discussed "life."

Per a New York Times report on the visit, Hope Hicks, former White House director of Communications and current Counselor to the President, said that the meeting had been requested by West.

Kanye tweeted that he met Trump to discuss "multicultural issues." His tweets about the meeting were later deleted in 2017.

In April 2018, West sent out a series of tweets expressing admiration for Trump, including that he was his "brother" and they both have "dragon energy."

In April 2018, West sent out a series of tweets expressing admiration for Trump, including that he was his "brother" and they both have "dragon energy."
John Legend, Chrissy Teigen, Kanye West, and Kim Kardashian.      Jeff Kravitz/MTV1415/FilmMagic

"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. 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," one of his tweets read.

Trump responded to his tweet saying, "Thank you, Kanye, very cool."

Fellow musicians John Legend and Chance the Rapper also got involved, with each offering their take.

Legend reached out to West directly, urging him to reconsider "aligning [himself] with Trump." Kanye posted a screenshot of their text exchange on Twitter.

Legend's wife Chrissy Teigen jokingly tweeted "are we still doing dinner Friday or no lol" at Kim Kardashian West. Teigen's Instagram stories from the weekend suggested that they were, indeed, still on for dinner.

Chance the Rapper initially came to West's defense, tweeting "Black people don't have to be democrats." He later apologized.

West solidified his position in the pro-Trump camp by visiting the White House later in 2018 and wearing the president's signature red "Make America Great Again" hat.

West solidified his position in the pro-Trump camp by visiting the White House later in 2018 and wearing the president
West and Trump in the Oval Office in 2018.      Getty Images

West paid a visit to the Oval Office in October 2018.

Surrounded by supporters and a throng of cameras, Trump and West talked about welfare, prison reform, and mental health, among other things. West said that putting on the red MAGA hat made him feel like Superman.

West also gave a signature 10-minute long monologue, at the end of which Trump said, "That was quite something."

The meeting was spoofed in a Saturday Night Live sketch.

Although he says he skipped voting in the 2016 elections, West said he would make his way to the polling booth this year and heavily alluded to President Trump as being the candidate with his support.

Although he says he skipped voting in the 2016 elections, West said he would make his way to the polling booth this year and heavily alluded to President Trump as being the candidate with his support.
West and Trump during their White House meeting.      Kevin Lamarque/Reuters

"We know who I am voting on," West said in a GQ interview from April 2020. "I will not be told who I'm gonna vote on because of my color," he added.

On the Fourth of July, West announced in a tweet that he was running for president in 2020.

On the Fourth of July, West announced in a tweet that he was running for president in 2020.
Kanye West.      Dimitrios Kambouris / Getty Images

Kardashian West and Tesla CEO Elon Musk tweeted their support.

In his tweet, West said, "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," followed by the American flag emoji.

Business Insider's Connor Perrett pointed out that the deadline to register as an independent candidate has passed in six states and the deadline is approaching in seven other states.

West told Forbes magazine's Randall Lane that he's running as an independent because Trump is in office. If he wasn't, he would have run as a Republican. He also said he doesn't support Trump anymore and that "I am taking the red hat off, with this interview."

West has enjoyed a more friendly relationship with Trump than with the last two presidents — President George W. Bush and President Barack Obama.

West has enjoyed a more friendly relationship with Trump than with the last two presidents — President George W. Bush and President Barack Obama.
Barak Obama and George Bush.      Associated Press/Pablo Martinez Monsivais

During a 2005 NBC program meant to aid relief efforts for Hurricane Katrina, a category 5 storm that has had a devastating impact on New Orleans, West said, "George Bush does not care about Black people."

Years later, while looking back at his term, President Bush said hearing West's comments was an "all-time low" for him.

President Obama once called West a "jackass," referring to his very public confrontation with Taylor Swift during the 2009 VMAs.

West included President Obama in the lyrics of his 2010 cult-classic song "Power": "They say, I was the abomination of Obama's nation. Well, that's a pretty bad way to start the conversation."

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