Kimberly Guilfoyle’s career has taken another dramatic turn after President Donald Trump’s administration pushed her out as US ambassador to Greece.
While allegations surrounding her conduct in office have dominated headlines, fresh claims from a former Fox News colleague have also revived scrutiny of Guilfoyle’s personal life and behavior during her time in television.
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Lisa “Kennedy” Montgomery, a former MTV VJ and Fox News contributor, has alleged that Guilfoyle openly discussed her sexual relationships with colleagues and showed them explicit photographs. The claims appeared in an article published by the Daily Mail on Thursday, October 15.
Kennedy said the pair initially connected over their “shared disdain” for California Governor Gavin Newsom, Guilfoyle’s former husband.
However, she claimed their relationship became increasingly uncomfortable as she learned more about Guilfoyle’s behavior away from the cameras.
According to Kennedy, Guilfoyle once discussed a man she called “Lex Luthor,” whom she allegedly described as a “lovesick cash cow.”
“Kimberly showed me and several of our friends pictures of his Amex black card – front and back,” the former MTV VJ wrote. “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.”
Kennedy also claimed that Guilfoyle acquired cryptic nicknames within the network, including “Seabiscuit” and “USO,” as a result of her alleged sexual escapades.
“In fact, Kimberly talked about sex so cavalierly that she made Samantha from Sex and the City seem like Greta Thunberg,” she quipped.
Kennedy characterized Guilfoyle as both “insanely charming” and a “status-chasing monster,” accusing her of displaying “unrelenting narcissism.”
These are allegations made by a former colleague, rather than independently established findings. Guilfoyle and her lawyer did not immediately respond to the New York Post’s request for comment on the latest claims.
From Fox News star to political controversy
Guilfoyle, a former prosecutor who built a national profile as a television personality, worked at Fox News from 2006 until 2018.
She later became a prominent supporter of Trump and joined his 2020 presidential campaign, eventually developing a high-profile relationship with his eldest son, Donald Trump Jr. The pair became engaged but separated in 2024.
Her departure from Fox News was itself controversial. She left the network in 2018 amid reports of a sexual harassment investigation.
In 2020, The New Yorker published an investigation alleging that Guilfoyle engaged in “graphic sexual talk” and “often shared lewd images,” including “photographs of male genitalia.”
Guilfoyle denied wrongdoing at the time, telling the publication: “I have never engaged in any workplace misconduct of any kind,”
Her appointment as ambassador to Greece represented a significant shift from media and campaign work into diplomacy. Trump nominated her in December 2024, and the Senate confirmed her in September 2025.
During her tenure, she promoted US commercial interests, including energy cooperation, but her posting ultimately became overshadowed by allegations about her conduct and relationships with politically connected figures.
The White House asked Guilfoyle to resign in October 2026 after reports alleged that she sought financial favors from a political donor.
The Wall Street Journal reported that she asked Republican donor and former congressional candidate Eric Deters for $100,000 to pay her American Express bill ahead of her confirmation hearing, allegedly offering access to administration officials in return.
Guilfoyle denied wrongdoing and announced that she would leave the role. Trump had publicly expressed dissatisfaction with the situation before the White House confirmed that she had been asked to step down.
The State Department’s Office of Inspector General also launched an investigation into her conduct, according to reporting by CBS News and The Washington Post.
The new claims about her time at Fox News add another chapter to a public career marked by media success, political influence and recurring controversy.
However, the allegations about her private life should be distinguished from the separate questions surrounding her official conduct as ambassador. Neither set of claims, by itself, establishes wrongdoing without further evidence or findings.