Donald Trump on Lindsay Lohan in 2004: ‘Deeply Troubled’ Women Are the ‘Best in Bed’

UPDATE: A representative for Lindsay Lohan gave a statement to CNN on Friday, October 14, about the past comments. “Right now, Lindsay is choosing to focus on the positive things happening in her life and has decided to disregard the comments made about her by Presidential nominee Donald Trump,” the statement read. “She is focusing on helping children around the world in need and that’s where her passion is.”

ORIGINAL STORY: Donald Trump spoke crudely not just about his eldest daughter, Ivanka Trump, on The Howard Stern Show. Back in 2004, the GOP presidential candidate, 70, gave his two cents about Lindsay Lohan, who is four years younger than Ivanka.

“What do you think of Lindsay Lohan?” Trump asked Stern, 62, during the interview, which was unearthed by CNN.

“I think she’s hot,” Stern replied.

Donald Trump Lindsay Lohan
Donald Trump and Lindsay Lohan RHONA WISE/AFP/Getty Images; Danny Martindale/

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Trump agreed, but admitted he wasn’t keen on the former child star’s freckles. “There’s something there, right? But you have to like freckles. I’ve seen a, you know, close up of her chest and a lot of freckles. Are you into freckles?” he said. “I’m not into freckles, but the red hair thing I like.”

The interview happened during the height of Lohan’s success with her blockbuster smash Mean Girls. “Can you imagine the sex with this troubled teen?” Stern asked during their chat. Trump replied, “She’s probably deeply troubled and therefore great in bed. How come the deeply troubled women — you know, deeply, deeply troubled — they’re always the best in bed?”

Despite Stern calling Lohan “troubled” in 2004, the actress’ first stint in rehab was at the Wonderland Treatment Center in L.A. in January 2007.

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The mogul has never held back with Stern. In a February 2007 chat (also spotlighted by CNN), he slammed his longtime enemy Rosie O’Donnell. (Their feud began in December 2006 when O’Donnell, 54, lashed out at him during The View.)

“Is there nothing she could do to get back in your good graces? If she came in and blew you?” Stern asked Trump about the comedian.

Rosie O’Donnell and Anna Nicole Smith
Rosie O’Donnell and Anna Nicole Smith Walter McBride/; Vince Bucci/Getty Images

“No, I’d pay a lot of money for that not to happen,” Trump said. “That’s one of the most unattractive people. She took great offense at the fact I said she better be careful or I, or one of my friends, would go and pick up her wife [Kelli Carpenter].”

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Trump and O’Donnell have yet to call a truce. Last month, during the first presidential debate, Trump defended calling her a slob and loser in the past. “I said very tough things to her,” he said. “And I think everybody would agree that she deserves it, and nobody feels sorry for her.”

In 2007, Trump poked fun at the late Anna Nicole Smith too — four days after she had died at age 39 of an overdose. “It looks like she had the lips pumped,” he told Stern at the time. “For all of your many women listening why do women have their lips pumped? It is the most disgusting thing to look at these big fat pumped-up tires.”

Listen to Trump’s interview about Lohan in the video above.

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