The Republican presidential candidate, who has a history of making sexist and derogatory comments about women, was interviewed by HLN's Showbiz Tonight in 2013 about Kardashian's decision to register for baby shower gifts despite being worth millions.
"She's a nice person," he said of the Keeping Up With the Kardashians star, who appeared as a guest on Trump's reality show, The Apprentice, in 2010. "I've known her over the years. She's really a nice person."
But then he made an unprompted comment about her appearance.
"She's gotten a little bit large," he said of the star, who was expecting daughter North West at the time. "I would say this, I don't think you should dress like you weigh 120 pounds."
The reporter shot back asking, "Why not? She feels good about herself."
That prompted Trump to hastily reply, "I think that's great. If she feels good about herself, do it, Kim."
After reports surfaced last week that Kardashian was planning to vote for Trump in the presidential election in November, she took to her website on Saturday, September 24, to clarify and let everyone know that she's supporting Democratic candidate Hillary Clinton.
"I believe Hillary will best represent our country and is the most qualified for the job," Kardashian, 35, wrote. "This year, I'm not just voting for myself, but also for my children, and I took that into careful consideration when I made my decision."
During the first presidential debate on Monday, September 26, Clinton took aim at the real estate mogul for calling women "pigs, slobs and dogs," and referenced his treatment of former Miss Universe Alicia Machado, who he called "Miss Piggy" among other hurtful nicknames.
Rather than back down, Trump — who owned the Miss Universe pageant until last year — doubled down on his criticism the morning after the debate, telling Fox & Friends that she was "the worst" Miss Universe ever. "She gained a massive amount of weight, and it was a real problem," he added.
Machado, 39, said in an interview on the Today show on Wednesday, September 28, that his insults contributed to her eating disorder.
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