In an interview with CNN host Anderson Cooper, former Playboy model Karen McDougal talked at length about an affair she claimed to have conducted with President Donald Trump beginning in 2006. One of the most notable details in the conversation was her statement that Trump compared her to his eldest daughter, Ivanka.
“He said I was beautiful like her and, you know, ‘you’re a smart girl.’ There wasn’t a lot of comparing, but there was some. I heard a lot about her,” McDougal told Cooper.
Most fathers are more than happy to sing the praises of their daughters’ brains and beauty, but Trump’s regard for Ivanka seems to be far beyond the norm — especially in comparison to his youngest daughter, Tiffany.
While McDougal seems to think that Trump’s comments about Ivanka were not that out of line, the president has a long history of strange actions and remarks about Ivanka.
During a 2011 interview with InTouch magazine about an affair that she claims to have conducted with Trump in 2006, porn actress Stormy Daniels said that Trump compared her to Ivanka as well. “He told me once that I was someone to be reckoned with, beautiful, smart, just like his daughter,” she said.
In an October 2016 news story, the Associated Press reported that eight former crew members of “The Apprentice” said Trump frequently made remarks about having sex with show contestants and also allegedly compared a camera operator’s attractiveness to Ivanka. The New York Times reported in May of 2016 that a former Miss Universe winner claimed Trump had asked her if his daughter was “hot,” when Ivanka was 16 years old.
But it isn’t just others saying that Trump has made remarks about his daughter’s sex appeal. He has made similar comments during publicly broadcast radio and television interviews. Trump has even used the same phrasing to describe another porn star whose appearance he admired.
During a February 12, 2007 appearance on radio host Howard Stern’s show, Trump heaped praises on Anna Nicole Smith, the late adult film actress.
“When she came to New York, I saw Anna Nicole Smith the first day or week that she was in New York. She was 6 feet tall. She had the best body. She had the best face. She had the best hair I’ve ever seen,” he said.
Trump’s accolades for Smith echoed words he used to admire Ivanka, then 22, during a January 7, 2004 conversation with Stern.
“You know who’s one of the great beauties of the world, according to everybody? And I helped create her, Ivanka,” Trump boasted.
He continued: “My daughter, Ivanka. She’s 6 feet tall, she’s got the best body. She made a lot money as a model—a tremendous amount.”
During a March 6, 2006 joint appearance on the daytime TV talk show “The View,” Trump joked about dating Ivanka, when asked what he would think if he saw that she had posed for Playboy.
“It would be really disappointing — not really — but it would depend on what’s inside the magazine,” he said.
“I don’t think Ivanka would do that, although she does have a very nice figure. I’ve said if Ivanka weren’t my daughter, perhaps I’d be dating her.”
The next year, Trump brought up this remark during an October 10, 2007 conversation with Stern. He claimed that he was simply just trying to be amusing. “I’m kidding. I’m kidding around, I’m having fun,” he said, saying that media organizations loved taking him out of context.
Later in the interview, however, Trump brought up Ivanka on his own initiative when Stern asked him who he would be dating if he were single.
“There aren’t too many of them. I’ll tell you, I know you and I have discussed this over the years,” Trump replied. “The most beautiful women aren’t the major celebrities because you know you can name like, you know, somebody told me Charlize Theron.”
“To be honest, I think Ivanka is much better looking than her,” Trump said, after Stern told him he thought the actress was “hot.”
Later in the interview, Trump again mentioned Ivanka unprompted when Stern asked him to name someone famous who had a “10” attractiveness rating.
“Umm, Ivanka,” the future president replied. Paris Hilton was the only other woman Trump could think of in addition.
During an appearance almost exactly one year earlier, on October 10, 2006, Trump discussed Ivanka’s breasts after Stern asked him if his daughter had gotten breast augmentation surgery.
“No, she didn't. I mean I would know if she did. The answer is no. Why? Did she look a little more fat?” he replied. “She’s actually always been very voluptuous,” Trump added.
During the 2016 Republican National Convention, Trump’s critics took aim at his embrace of Ivanka after she introduced him as the final speaker:
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