Kimberly Guilfoyle Faced Her Fair Share Of Controversy Long Before Don Jr. Entered The Picture

Ever since Donald Trump Jr. and Kimberly Guilfoyle have been engaged, most of the controversy surrounding the conservative couple has to do with Trump Jr.'s father, former President Donald Trump. But as it turns out, Guilfoyle has her own fair share of scandalous skeletons in the closet. 

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Decades before she would become a soon-to-be member of the Trump family, Guilfoyle was a respected California attorney who won several awards for her work in adult and juvenile cases. The most salacious of Guilfoyle's controversies didn't seem to arise until she began working with Fox News in 2006, where she would stay until 2018.

From alarming sexual harassment allegations to divisive comments as a co-host of "The Five," Guilfoyle has made headlines multiple times in her career, none of which had to do with her fiancé's family. Like, for example, when she opined in August 2014 that she wished Russian President Vladimir Putin or Israeli Prime Minister Benjamin Netanyahu would come take over the United States for a day or two. And no, the hot button hot takes didn't stop there.

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Kimberly Guilfoyle said she didn't think attractive women should vote

Two months after Kimberly Guilfoyle made her controversial remarks about Vladimir Putin and Benjamin Netanyahu, the Fox News personality got herself back in the hot seat with a highly divisive stance on who should (and who shouldn't) be allowed to vote or serve on juries. At the time, Guilfoyle and the rest of her "The Five" colleagues were discussing how younger people tend to be less conservative than older people.

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"When you're young like that, you think — same reason why young women on juries are not a good idea, they don't get it," Guilfoyle said. "They're not in that same life experience of paying the bills, doing the mortgage, kids, community, crime, education, healthcare. They're like healthy and hot and running around without a care in the world" (via The Hollywood Reporter).

When a fellow co-host pushed back on the idea that young, attractive women shouldn't be disqualified from serving on a jury, Guilfoyle said: "I didn't say they shouldn't be. I just thank and excuse them so they can go back on Tinder and Match.com." The UC Davis and University of San Francisco School of Law grad (and former underwear model) later said the public outcry about her comments was a targeted smear campaign spearheaded by progressive watchdog group Media Matters for America.

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She was also at the center of alarming sexual harassment allegations

Kimberly Guilfoyle's history of questionable conduct isn't limited to her brash on-air personality, either. A shocking 2020 exposé by the New Yorker revealed that Guilfoyle's abrupt departure from Fox News in July 2018 was catalyzed by allegations of Guilfoyle's inappropriate, sexual behavior with her colleagues. According to the The New Yorker, these accusations were summarized in a 42-page complaint written by Guilfoyle's assistant, which the anonymous employee then sent to Fox News' executive board.

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Because Fox News and the assistant settled outside of court to the tune of around $4 million, the specific letter is unavailable to the public. However, reporter Jane Mayer corroborated some of the accusations, including that the Fox News personality required her assistant to work at her apartment while Guilfoyle was almost or fully naked. The New Yorker also confirmed that Guilfoyle repeatedly showed colleagues photographs of genitalia, showed pornographic videos in her office, and engaged in so much explicit sexual talk that hair and makeup artists filed internal complaints.

While Guilfoyle and her supporters have denied wrongdoing, Fox News' multi-million-dollar payment to the assistant regarding these accusations is public record. And indeed, the whole situation conjures up similar images to Guilfoyle's future father-in-law's hush money trial for payments he allegedly made to keep former adult star Stormy Daniels quiet about their affair.

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