5 Times Kimberly Guilfoyle Took Her Support Of Donald Trump Too Far

Former Fox News personality Kimberly Guilfoyle has certainly faced her fair share of controversy long before she became a member of former president Donald Trump's innermost circle. But some of her more eyebrow-raising moments undoubtedly happened after she became an employee (and — later — a future daughter-in-law) of the ex-POTUS.

Guilfoyle left her post as an on-air personality for Fox News in the summer of 2018 and immediately began working for a super PAC to help raise funds for Trump's political campaign. At the time, Donald Trump Jr. and Kimberly Guilfoyle's relationship timeline had already begun. So, too, did Guilfoyle's outspoken support of the former president, resulting in a laundry list of cringey, awkward, or downright inappropriate behavior.

From offering up lap dances on the heels of a sexual harassment scandal to using Donald Trump's re-election as motivation to marry his oldest son, here are five times Guilfoyle took her support of Donald Trump too far.

The height of the COVID-19 pandemic coincided with the 2020 presidential election, which meant both then-presidential hopeful Joe Biden and then-President Donald Trump had additional obstacles when it came to navigating the campaign trail. But for the latter candidate, he had yet another challenge to face on the road: Kimberly Guilfoyle.

According to November 2020 reports by Politico, Guilfoyle's outlandish behavior at political fundraisers shocked constituents (and, unfortunately for Trump, potential donors). Not only did Guilfoyle reportedly talk about her sex life frequently, but she even offered inappropriate rewards to whoever donated the most money to Trump's campaign, including lap dances and hot tub parties with the former TV personality.

Of course, offering constituents lap dances and hot tub soaks would be bad enough on its own. But the inappropriate comments were made even worse by the fact that Guilfoyle was coming off the heels of a sexual harassment scandal that led to her departure from Fox News. "According to a dozen well-informed sources familiar with her complaints, [an] assistant alleged that Guilfoyle, her direct supervisor, subjected her frequently to degrading, abusive, and sexually inappropriate behavior," the New Yorker reported. While Guilfoyle denied any wrongdoing in relation to that scandal, her offers to provide sexual favors to donors certainly wasn't good timing on her part.

Donald Trump Jr. and Kimberly Guilfoyle began dating shortly after Trump split from Vanessa Trump, his ex-wife and mother of his five children. Trump Jr. and Guilfoyle became a campaign trail power couple, appearing at rallies and on television as a united front in support of former President Donald Trump. This "united front" was put under particularly intense fire during a tumultuous interview on ABC's "The View."

Most of the conversation involved Trump Jr. butting heads with the talk show's panel of hosts, but occasionally, Guilfoyle would interject with a comment or two. For example, when Abby Huntsman asked Guilfoyle when she and her boyfriend were planning on getting hitched, the attorney said, "Oh my god ... If he can get the president re-elected!" (via People).

Don Jr., for his part, responded in kind. "I like to joke on the campaign trail," he explained at one point. "You know, my biggest sacrifice for America is having to travel with Kimberly. I can't say that on this take without getting destroyed." Guilfoyle and Trump Jr.'s conversation took place about a year before the couple got engaged in December 2020, even though Donald Trump lost his bid for re-election.

Kimberly Guilfoyle might be a loyal supporter of former President Donald Trump, but that doesn't mean she's doing it for free. Guilfoyle came under fire after the House select committee in charge of investigating the Capitol riot on January 6, 2021, discovered a conservative pro-Trump organization called Turning Point Action paid Guilfoyle $60,000 to make a three-minute speech at a rally immediately following the insurrection.

Guilfoyle was paid to introduce her fiancé Donald Trump Jr. at an event called "Stop the Steal." The House committee believed Guilfoyle's hefty payment was proof that the Trump family was financially benefiting from pushing false narratives about the "stolen" election in November 2020. Ironically, Guilfoyle's payment also harkens back to rumors about how the Trump family really felt about Guilfoyle early on.

Stephanie Grisham, "I'll Take Your Questions Now" author and former aide to Melania Trump, said that the ex-FLOTUS was wary of people who tried to make money off supporting her husband. "She didn't like people profiting off of her husband or her family," Grisham said in an interview with MSNBC (via Yahoo! Money). "Guilfoyle demanded, I believe, $60,000 just to introduce the president the day of the rally; it was things like that that bothered her."

In other instances, Kimberly Guilfoyle's support of her future father-in-law Donald Trump crossed the line in the form of unusual decor in her home with Trump's son, Donald Trump Jr. The oddest addition to their Floridian mansion? A Christmas tree that the couple keeps on display in their home year-round that they've nicknamed the "patriot tree," per reporting by Page Six.

Guilfoyle and Trump Jr.'s "patriot tree" features red, white, and blue baubles and pro-Trump ornaments like miniature MAGA hats, "Let's Go Brandon" knick-knacks, and other conservative American imagery. The tree itself has faux snow-covered boughs, allowing the colorful, tongue-in-cheek ornaments to really pop.

As if having a year-round tree dedicated to your political beliefs wasn't enough, Trump Jr. and Guilfoyle placed the tree in front of a massive graffiti-style painting of the ex-POTUS, which features Donald Sr. looking up through his brow in front of an American flag. "Trump 2024" and "In Trump We Trust" are written on either side of his likeness.

Of all the awkward Kimberly Guilfoyle moments that were captured by millions, her half-screamed speech at the Republican National Convention is perhaps the hardest to watch — or hear, for that matter. Still in the midst of the COVID-19 pandemic, Guilfoyle presented her speech to an empty gymnasium, keeping eye contact with the cameras to address audiences watching from their quarantine bubbles.

Guilfoyle's constant hollering, paired with an eerie lack of background audience noise, made for a dystopian blip of American history that comics and critics pounced on moments after her speech was finished. Late night talk show hosts used Guilfoyle's speech as ample fodder for jokes, including CBS' "Late Show" host Stephen Colbert, who called Guilfoyle "a vengeful banshee who will haunt your dreams" (via AP News).

"This is the first time in my life I had to turn down the volume on C-SPAN," Colbert riffed. Speaking to his wife, he continued, "I'm glad we already have kids because I think I was sterilized by that." Indeed, Guilfoyle's cringey speech might have been a particularly awkward moment of the 2020 election cycle. But as this list shows, it certainly wasn't the last Guilfoyle moment to give us major secondhand embarrassment, and we don't doubt there will be more moments like that in the future.