The Ups And Downs Of Kim Kardashian's Relationship With Donald Trump

Former President Donald Trump and Kim Kardashian were once friendly collaborators, but things turned frosty. Where did it all begin with the two reality TV moguls? On TV, of course. In 2010, Kim guest-starred on Trump's reality competition show "The Apprentice." Contestants built displays for Kim's perfume in Perfumania stores, and Kim surprised them as one of the judges.

Things were genial between Trump and Kim. When deliberating about the challenge's winner, Trump complimented Kim's perfume and her sister, Khloe Kardashian, who had been a contestant on "Celebrity Apprentice." He said, "And Khloe is terrific, she really is. She did great on the show and she's a terrific person, just like you are" (via YouTube). However, his kind words for Kim's sister were a stark contrast to what he had apparently said while she was on his show. According to sources for HuffPost, Trump was nasty about Khloe behind her back: "He said, 'Why don't we fire Khloe? She is a fat piglet. Why did we get the ugly Kardashian?'" 

When Kim was pregnant with her daughter North West in 2013, Trump body-shamed her too. In an interview on "Showbiz Tonight" from HLN, Trump said, "She's a nice person. I've known her over the years. She's really a nice person" (via Us Weekly). However, he also said, "She's gotten a little bit large. I would say this, I don't think you should dress like you weigh 120 pounds." Trump backpedaled when questioned about his statement.

Trump and Kardashian worked together on an important cause

Per CNN, Donald Trump also body-shamed Kim Kardashian on multiple occasions on "The Howard Stern Show." It's unsurprising, since his "Access Hollywood" leaked tape scandal showed the vulgar way he discusses women. Despite that, and despite Kardashian saying she'd vote Hillary Clinton in 2016, Kardashian and Trump worked together on prison reform.

In 2018, Kardashian joined him at the White House to discuss the issue and to ask him to pardon Alice Marie Johnson after 21 years behind bars. The then-63-year-old was given a life sentence for working with a drug ring and passing messages along. In a statement, Kardashian thanked Trump for meeting with her and said, "It is our hope that the President will grant clemency to Ms. Alice Johnson who is serving a life sentence for a first-time, non-violent drug offense. We are optimistic about Ms. Johnson's future and hopeful that she — and so many like her — will get a second chance at life" (via CNN). Trump pardoned Johnson one week later.

Later in 2018, the First Step Act became a law — a big deal for federal criminal justice reform. Kardashian returned to the White House in 2019 and gave a speech about hiring prisoners following their incarcerations. Trump and Kardashian shared kind words, with Kardashian saying, "And I just want to thank the president for really standing behind this issue, and seeing the compassion that he's had for criminal justice has been really remarkable" (via YouTube).

Trump later didn't help Kardashian

Kim Kardashian and Alice Marie Johnson both went to the White House in 2020 and advocated for three other prisoners to be pardoned. After his time in office, Donald Trump didn't help anymore. Jonathan Karl's book "Tired of Winning" outlines Trump's years following the 2020 election. Near the end of his term, Kardashian asked for additional prisoners to be pardoned. A source told Karl that Trump wanted something in return: "He would grant the commutations, he told Kardashian, if she leveraged her celebrity connections to get football stars who were friends of hers to come visit him at the White House." She attempted to do so, but no one would visit Trump at that point.

Later on, Trump refused to endorse another prisoner seeking clemency when Kardashian asked: "Hell no, the former president told her. He wouldn't do it. 'You voted for Biden and now you come asking me for a favor?' Trump told her." (Kardashian never disclosed her 2020 vote but shared a seemingly celebratory social media post about Joe Biden.) Trump reportedly hung up on Kardashian shortly after.

On "Jimmy Kimmel Live" in 2024, Kardashian admitted that Trump didn't seem to think highly of her. However, "I think he did amazing stuff with prison reform and let a lot of people out and signed an amazing bill, The First Step Act, and so that's what I'll focus on." Trump's opinion of Kanye West, Kardashian's ex-husband, reportedly took a turn too.