Co-Host of ‘The Five’ Accuses Kimberly Guilfoyle of NSFW Behavior – Was Guided by ‘Unrelenting Narcissism’

Everyone deserves a seventh chance. That’s why I and most of the conservative rank-and-file had reservations, but not necessarily hard questions when former Fox News host Kimberly Guilfoyle was appointed ambassador to Greece.

Yeah, she’d left Fox News years ago with a cloud over her head due to her workplace conduct. Sure, there were rumors out there that it was because of prurient misconduct, at that. (“All she talks about is d*** and money,” one source told veteran journalist Yashar Ali in 2018.)

Well, it’s money that finally got her chased out of her position as ambassador: A report in The Wall Street Journal last week indicated that she had texted with a Donald Trump donor before her confirmation hearing, begging him to wire $100,000 to pay off her American Express bill.

“Honey please I need you to get this done for me.”

How Kimberly Guilfoyle pressed a MAGA ally to transfer $100,000 to her Amex account. 🔗: https://t.co/NUTDNzex5Q https://t.co/G1OjMXRkQj

— The Wall Street Journal (@WSJ) October 8, 2026

“We didn’t like what we were reading,” President Trump told reporters after she was dismissed days after that article.

“She wasn’t a member of my family,” he added, noting that she was Donald Trump Jr.’s ex. “I guess she dated my son a long time ago.”

Ouch. We now return to the, ahem, prurient part of the equation, since one of her former co-workers is getting specific about what got her chased from Fox News.

In a piece first published in the U.K. Daily Mail on Thursday, Lisa “Kennedy” Montgomery — the former MTV host who became a Fox News contributor and a panelist on “The Five” — described her NSFW experience with her former co-worker in a piece titled “Kimberly Guilfoyle flaunted her nudes album to me… with each man’s Amex card next to his compromising photo.”

Keep on Daily Mail-ing, Daily Mail.

“Kimberly showed me and several of our friends pictures of his Amex black card — front and back,” Kennedy wrote in the piece. “The images were matched with a corresponding picture of the card holder’s private parts.”

“There were at least three sets of these credit card-penis pairings,” she added.

While Kennedy called Guilfoyle “insanely charming,” she also said she was a “status-chasing monster” driven by “unrelenting narcissism” — all with a fixation that explains why she was chased from the network over sexual harassment allegations.

“Kimberly talked about sex so cavalierly that she made Samantha from ‘Sex and the City’ seem like Greta Thunberg,” Kennedy said.

She also allegedly took advantage of men, including one she called “Lex Luthor” who was a “lovesick cash cow.”

This, again, doesn’t sound great when she apparently sent messages to a donor asking him to pay off her Amex bill with a message saying, “honey, please.” Just saying.

Guilfoyle, of course, has denied the claims.

“These allegations are false, and I intend to vigorously defend my name, my reputation, and my integrity,” Guilfoyle wrote in her farewell message.

“I have dedicated my professional life to fighting for justice, standing up for what is right, and defending the values that make America exceptional. I will not allow false accusations to define my decades of public service.”

Whether or not that’s the case is out of her hands, but at least — according to reports — she’s not going to let it get in the way of her favorite, erm, hobbies. From the New York Post’s Page Six:

A source tells Page Six that the former Fox News host — who just resigned as the US ambassador to Greece at the request of the White House amid allegations of improper and possibly illegal activity – is going to stay abroad and find the Aristotle to her Jackie.

Guilfoyle has denied all the allegations against her and vowed to “vigorously defend” herself.

“She is embarrassed to come back to the US. She’s ashamed,” says the insider, who tells us the plan is to find a “rich husband in Europe.”

Well, maybe that’s for the best. “She’s done in Trump world,” the source said. “Who will hire her? No one will go near her.”

She had her seventh chance and, from all appearances, blew it. They shouldn’t go near her, with cause.

And if the rich husband thing doesn’t work, there’s always turning Democrat.

I hear her most famous ex not named Donald Trump Jr., California Gov. Gavin Newsom, isn’t terribly discriminating in these matters. But then, like Trump Jr., he’s probably thankful he dodged this bullet.

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