Kimberly Guilfoyle: From the Trump Family Circle to an On-Air Dismissal

From former fiancée of Donald Trump Jr. to Washington's ambassador to Greece, Kimberly Guilfoyle's rise was linked to her closeness to the US president's family and presence in its political circles. But press reports about her conduct and potential conflicts of interest reversed her trajectory, after the White House announced on air that the president had asked her to resign.

Gilfoyle's story began attracting attention with her relationship with the eldest son of US President Donald Trump, where the two owned a $9.7 million home in Florida, appeared together at the president's election rallies, and exchanged emotional posts via social media.

Gilfoyle wrote in an "Instagram" post for Valentine's Day on February 14, 2022: "I fall more in love with my fiancé every day. Donald Trump Jr., you are my best friend, my rock, and the man I will spend the rest of my life with."

Trump Jr. wrote in 2024: "Thank you for always standing by my side, no matter what the haters throw at us. Love you."

Today, however, Trump Jr. has married a high-society lady and fashion model from Florida. In return, Gilfoyle lost her job after a series of press reports published by the "Wall Street Journal" revealed embarrassing incidents.

Suspicious Incidents
These incidents included Gilfoyle asking a Republican donor to pay off $100,000 of her "American Express" credit card dues, shortly before her confirmation hearing in the Senate in July 2025. The president had nominated her for the position of Ambassador to Greece shortly after she broke off her engagement to his son two years prior.

Gilfoyle's rise, at age 57, and subsequent fall were not surprising within the White House, where many saw her as a "showy personality who loves parties," whose actions raise doubts about her judgment, according to the "New York Times."

But her supporters said that behind the glamorous appearance lies a serious character. Gilfoyle worked as a former host on the "Fox News" network, and also served as a public prosecutor in San Francisco and Los Angeles. She was previously married to Gavin Newsom, who later became Governor of California and one of Trump's most prominent critics in the Democratic Party.

In any case, Gilfoyle was among those close to Trump, holding a prominent status within his family and political team. The newspaper stated that the speed of the president's dismissal of her showed his willingness to abandon anyone who becomes a burden or source of embarrassment. But it also left her without much reason to continue loyalty to the president and his family, at a time when Trump's political power is waning.

In announcing her resignation, Gilfoyle denounced what she described as "false accusations," saying she would vigorously defend her reputation. As for Trump, he did not offer anything during his remarks to journalists outside the White House suggesting he would keep her within his inner circle.

He said: "She was not part of my family. I think she dated my son a long time ago."

An Unusual Choice
Gilfoyle had arrived in Greece less than a year ago, in a choice that was "highly unusual" from the start.

According to the "New York Times," Donald Trump Jr. was the one who enabled her to get the position, albeit indirectly. In December 2024, he was seen holding hands with society lady and fashion model Bettina Anderson as they left a restaurant in Palm Beach. The next day, President-elect Trump announced the selection of Gilfoyle as US Ambassador to Greece.

The timing of the announcement suggested the president wanted to remove her from the country at an embarrassing time for his son, who married Anderson this year. Gilfoyle's allies denied this was the reason, but Greeks wondered at the time whether they would simply receive the woman abandoned by the president's son.

A Center of Attention in Greece
In Athens, Gilfoyle became the talk of the town upon her arrival on a private jet owned by a Greek-American businessman. She wore a semi-transparent black evening dress during a dinner held during Thanksgiving week, joked with the Greek president while presenting her credentials saying she was looking for a new husband, and continued staying out until the early hours of the morning in the capital's nightclubs.

Gilfoyle said in an interview with the "New York Times" last year, referring to her arrival at a nightclub to attend a show starting at 01:30 AM for her boyfriend, Konstantinos Argyros, one of Greece's most famous pop singers: "I wasn't late, I arrived just before three."

Celebrity photographers chased Gilfoyle wherever she went, but Greeks said at the time that she was working as hard as she was enjoying her time.

Given the nature of her position and what they perceived as her access to the White House, they considered her one of the most influential figures in the country. Conversely, the page of her statements on "Fox News" during the Greek debt crisis in 2015, when she described Greeks as "freeloaders," was largely turned over.

Early in her mission, Gilfoyle announced two important commercial agreements, namely the development of a port near Athens with American support, and natural gas exploration off the island of Corfu. Work on both projects had begun long before her arrival in Athens, but Greek officials said she engaged with the plans months earlier and wanted to announce them during her tenure.

Adonis Georgiadis, the Greek Minister of Health and deputy leader of the ruling conservative party, was among those impressed by her performance. He said: "When her appointment was first announced, people asked: Who is this?" But he added that if she succeeds in achieving results, "who cares if she wears a transparent dress?"

Rapid Fall
The journey of her downfall began last month, after the "Wall Street Journal" published a report dealing with Gilfoyle and potential conflicts of interest related to energy deals in the Balkan region.

Gilfoyle resigned on Tuesday, but denied the accusations against her, saying she would defend herself "vigorously," according to the "Associated Press."

Gilfoyle said in a post on the "X" platform that the accusations were "false," affirming her determination to defend her name, reputation, and integrity. She added that she would not allow "false accusations" to tarnish her career, which she described as spanning decades of public service.

It remains unclear what Gilfoyle will do now. She previously worked as a legal analyst for CNN and ABC networks in New York, before her career at "Fox News" ended in 2018. Two people familiar with the circumstances of her departure then said she was forced to leave due to questions regarding inappropriate behavior in the workplace.

The "New Yorker" magazine reported two years later that Gilfoyle was forced to leave the network following sexual harassment allegations made by an assistant.

The magazine reported that the assistant received a settlement worth more than $4 million. Gilfoyle denied the accusations through her lawyer at the time, and refused to comment on them during her interview with the "New York Times" last year.