A complete timeline of Trump's tumultuous relationship with Kim Kardashian and Kanye West

Donald Trump's presidency, so far, has been bizarre and newsworthy for numerous reasons.

Many of his antics can be explained, dismissed or ridiculed, but one of the strangest things about Trump's first four years in the White House is his continuing relationship with Kim Kardashian and Kanye West, possibly the most talked about celebrity couple on the planet.

Almost since the 2016 election, Kim and Kanye, despite seemingly having nothing in common with Trump, apart from fame and wealth, have been connected to possibly the most divisive and detested president in history.

Although Kanye and Kim's interests in the president do dramatically differ their allegiance is curious in that they have flirted with supporting him but aren't the type of MAGA celebrities that we've seen over the last four years.

Kardashian's dealings with Trump mostly consist of her prison reform initiative, but West's is a little more tumultuous and controversial.

We'll probably never gain a full and complete understanding of this most unlikely pairing but if we trace back the entire timeline then we might uncover something that can help us find some sort of logic, so here goes:

1995: Trump speaks out in support of OJ Simpson

To find the first interaction between the Trumps and the Kardashians we have to go back a long, long way to 1995 and the murder trial of OJ Simpson.

This headline-making televised trial was one of the biggest stories in the world at the time, and everyone had an opinion – including Donald Trump. The future president was a guest on the 9 November 1995 edition of The Howard Stern Show, where he explained why he thought Simpson was innocent and had been framed for the murder of Nicole Brown and Ron Goldman. Newsweek quotes:

Trump: Well, I know how much you like O.J. and I know how, how innocent you feel he is.

Howard Stern: [Laughing] Yeah.

Trump: And because, you know, don't forget, there wasn't that much blood found in the Jeep. There was only about 50 drops.

Stern: Yeah, that's not, that's not that much. That could...

Trump: Yeah, it's a pretty sad deal, I'll tell you.

Stern: That could have been planted somehow.

Trump: Yeah it could have been. Fifty different people could have planted it.

Stern: Yeah. Unbelievable.

Trump: I don't think the LAPD is that smart.

Robert Kardashian, Kim's father, was one of Simpson's lawyers (and friends) during the trial.

2006: Kim and Ivanka run in the same social circles

Before Kardashian was a major reality television star and Ivanka was a senior adviser to the president, they were both socialites in the same social circles featuring people such as Paris Hilton.

Although they might not have been exactly, they definitely ran into each other from time to time, including a party at the VIP Room nightclub in Saint-Tropez in 2006.

This story reemerged in 2018, when Kardashian was snapped by paparazzi having dinner at the home of Ivanka and Jared Kushner in Washington DC

In 2017, Hilton confirmed that she had known Donald Trump since she was 19, after he signed her for his modelling agency, but that she didn't vote for him.

Speaking to Entertainment Tonight, Paris Hilton said:

I never said that I voted for him. I was asked if I liked him. I’ve known him since I was a little girl. But I never said I would vote for him.

2015: Kim Kardashian endorses Hillary Clinton for president

This is something that isn't mentioned much anymore but way back in August 2015, Kim Kardashian actually endorsed Hillary Clinton for president way before the 2016 election.

Kardashian shared a selfie with the former Democratic nominee which also featured Kanye in the background. Despite this, West said not long after the 2016 election that he didn't vote but 'would've voted for Trump.'

2016: Kanye West includes a nude model of Trump in his 'Famous' music video

Released a few months before the presidential election, Kanye included a Trump waxwork in his controversial music video for the song 'Famous'.

The Trump model was among 12 other nude models in a giant bed. They included George W Bush, Anna Wintour, Rihanna, Chris Brown, Taylor Swift, Kanye West, Kim Kardashian, Ray J, Amber Rose, Caitlyn Jenner and Bill Cosby.

2016: Kanye West meets Trump in Trump Tower after the election

Not long after the result of 2016 election, West went to meet the president-elect in Trump Tower, where Trump told reporters that the pair spoke about 'life' for around 40 minutes. The two then posed for photographs outside of Trump's gold elevator with Turmp adding: "Just friends, just friends. He’s a good man."

In since-deleted tweets, West said that he spoke to Trump about multicultural issues including bullying, supporting teachers, modernising curriculums and violence in Chicago.

2018: Kim Kardashian meets Trump in the White House

On 30 May 2018 Kardashian visited Trump, as well as Jared Kushner in the Oval Office, to campaign for prison reform and lobby for the release of a low-level drug felon named Alice Marie Johnson, who at that point had served more than 20 years in jail. In a statement at the time, Kardashian said:

I would like to thank president Trump for his time this afternoon. It is our hope that the President will grant clemency to Ms Alice Marie Johnson who is serving a life sentence for a first-time, non-violent drug offence. We are optimistic about Ms Johnson's future and hopeful that she – and so many like her – will get a second chance at life.

Shortly after this, Trump granted Johnson, who was 62 at the time, clemency and she was released from prison after two decades behind bars. Trump later pardoned her from any crime that she had been accused of. This is possibly one of the few things that president Trump has done that liberals can agree was a good thing.

2018: Kanye goes to visit Trump at the White House and has a very awkward meeting

Around 2018, West seriously started to lean into his support for and admiration of Trump. In a number of Twitter outbursts West lavished Trump with praise and the president retweeted the rapper, thanking him for his support. This was before his wife had visited the president who he called "a player" when he was asked if he was concerned about Kardashian meeting him, given his reported history with women.

By October of 2018 West was invited to the White House to talk about a variety of topics including urban revitalisation, prison reform and record highs of African American unemployment. Not all of that was discussed as West dominated the conversation, rambling about how the MAGA hat made him feel like Superman and presenting Trump with a design of a hydrogen plane which he dubbed the iPlane-1. For once, Trump was lost for words.

This led to Trump supporters holding West in high regard and Donald Trump Jr even praising the rapper's last album Jesus is Godwhich was one of the only favourable reviews the record received. Not long after all this, West said that he was "distancing myself from politics and completely focusing on being creative." This clearly didn't last long.

2019: Kim Kardashian speaks at the White House on criminal reform

In June 2019, Kardashian was invited back to the White House to speak about a ride-sharing programme that would help former prisoners get transportation to and from work and to job interviews. When introducing her to the crowd Trump said "I guess she's pretty popular."

2020: Kanye West announces that he is running for president

This is where things start to get a little uncomfortable. In July this year, without so much of a hint, West announced out of the blue that he was planning to run for president, despite it being far too late for him to get onto many of the ballots across the country.

Just a few weeks after announcing his candidacy, West gave a rally speech in Charleston, South Carolina, which doubled as a fashion event for his Yezzy line. During the controversial event, the rapper left people speechless after he suggested that slavery abortionist Harriet Tubman "never actually freed any slaves."

Trump said that he was watching West's campaign and that it could be a 'great trial run' ahead of a more serious bid in 2024. He had also gained support from Elon Musk however disturbing reports soon started to emerge from the campaign. On 12 August Forbes published an in-depth article on the relationship between West, who has bipolar disorder, and Jared Kushner, explaining that the two were in regular contact with each other, with friends of the rapper calling the conversations for Kushner's side 'reverse psychology.' Another friend is quoted as saying:

When you have people around him who have the best intentions and don’t need anything from him, you can steer him when he’s in that space into a positive place. When you have people around him who see him as an opportunity, they create a very, very bad scenario.

The New York Times also reported that Republicans were aiding West's campaign in either genuine sincerity and admiration or the hope that he could act a spoiler and take votes away from Joe Biden and the Democrats. At the time of writing, West managed to make the ballot for around 12 states, so he is unlikely to cause any major disruption at the election but is possibly the strangest chapter in West's relationship with the president.

2020: David Letterman grills Kardashian for not speaking out against Trump

Kardashian is a guest on David Letterman's newest season of My Next Guest Needs No Introduction for Netflix, which was released in October.

During the interview, Letterman grilled Kardashian for not being critical of Trump. Although Letterman could see what Kardashian had achieved with Trump, he admitted that it didn't make him feel any better about the president. While she didn't say anything negative about Trump she did reveal that she had been contacted by others warning her about the backlash she might receive:

Trust me, everyone called me and said, 'Don't you dare step foot in that White House or your reputation is done.

Letterman added:

It's a positive force that diminishes what I consider to be unacceptable behavior by the president.

Kardashian didn't say anything about Trump's 'unacceptable behaviour' but did add that she was "extremely grateful" for the work that she had done with them.

And for now, that is it for the tumultuous relationship between Trump, Kim and Kanye but its only the tip of the iceberg at least from the Kardashian side. For instance, Khloe Kardashian was a contestant on the Celebrity Apprentice and Caitlyn Jenner was even reportedly at Trump's inauguration.

Whether Trump is reelected on 3 November or not will remain to be seen but we feel that this probably isn't the last time that this collection of people's paths will cross...

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