It started out so well for her.
Kimberly Guilfoyle, the U.S. ambassador to Greece until she was effectively fired on live television on Tuesday when the new White House press secretary said that President Trump had asked for her resignation, was at one point engaged to Donald Trump Jr., the president’s eldest son. The couple owned a $9.7 million home in Florida, appeared at Trump rallies together and sent each other adoring posts on Instagram.
“Falling in love with my fiancé more and more every day,” Ms. Guilfoyle posted on Instagram on Valentine’s Day 2022. “@donaldjtrumpjr, you’re my best friend, my support system and my forever guy.”
“Thanks for always being there no matter what the haters are throwing our way,” he posted in 2024. “I love you.”
Today, the junior Mr. Trump is married to a Florida socialite and model. And Ms. Guilfoyle, who was nominated as ambassador to Greece by the president soon after her engagement to his son was broken off two years ago, is out of a job after a series of damning reports in The Wall Street Journal, including that she asked a Republican donor to pay off $100,000 on her American Express credit card just before her Senate confirmation hearing in July 2025.
The rise and fall of Ms. Guilfoyle, 57, was not a surprise at the White House, where many saw her as a flamboyant party girl with questionable judgment.
Her supporters said she was in fact a substantive person underneath the glitz. Ms. Guilfoyle, a former Fox News host and a former prosecutor in San Francisco and Los Angeles, was once married to Gavin Newsom, who would go on to become governor of California and one of the Democratic Party’s most outspoken critics of Mr. Trump.
Either way, Ms. Guilfoyle was a Trump insider with a prominent role in the family and its political operation. The president’s swiftness in firing her showed his willingness to cut off anyone who becomes a liability and an embarrassment. But it also left her with little reason to remain loyal to the president and his family at a time when Mr. Trump’s political authority is ebbing.
In announcing her resignation, she decried what she called false accusations and said she would vigorously defend her reputation. Speaking to reporters outside the White House, Mr. Trump did little to suggest he would continue to keep her close.
“She wasn’t a member of my family,” he said. “She, I guess, dated my son a long time ago.”
Ms. Guilfoyle, who arrived in Greece less than a year ago, was a highly unusual choice for the role to begin with.
In a sense, it was Don Jr. who got her the job, indirectly. In December 2024 he and the socialite and model, Bettina Anderson, were seen holding hands as they left a Palm Beach restaurant. The next day, President-elect Trump announced that Ms. Guilfoyle was his pick to be ambassador to Greece.
The timing suggested the president wanted her out of the country at an awkward time for Don Jr., who married Ms. Anderson this year. Ms. Guilfoyle’s allies said that was not the case, although Greeks at the time wondered if they were simply getting the woman who had been jilted by the president’s son.
In Athens, Ms. Guilfoyle became a sensation as soon as she arrived, on the private jet of a multimillionaire Greek American businessman. She wore a partly sheer black evening dress to a Thanksgiving week dinner, joked with the Greek president when she presented her credentials that she was working on finding a new husband and stayed out until the small hours of the morning at Athens nightclubs.
“Oh, I wasn’t late, it was like before 3,” Ms. Guilfoyle said in an interview with The New York Times last year, referring to how she had turned up at a nightclub for the 1:30 a.m. premiere show of her friend, one of the country’s most famous pop singers, Konstantinos Argiros.
Paparazzi followed her everywhere, but Greeks at the time said Ms. Guilfoyle worked as hard as she played. By the nature of her position and what they saw as her access to the White House, they viewed her as one of the most important people in the country. Mostly forgotten were her words on Fox during the Greek financial crisis in 2015, when she called Greeks “freeloaders” who should be punished like a dog that “pees on the rug.”
Early on, Ms. Guilfoyle announced two important business deals, the development of a U.S.-backed port near Athens and the exploration for natural gas off the island of Corfu. Both were in the works long before she arrived in Athens, but Greek officials said she had jumped into the plans months earlier and wanted them announced on her watch.
Adonis Georgiadis, Greece’s health minister and a vice president of the governing conservative party, was among those impressed. “When she was first named, the people were, ‘What’s that?’” he said. But if she delivers, he said, “who cares if she has a see-through dress?”
Her downfall began last month, after The Journal reported about Ms. Guilfoyle and her potential conflicts of interest over energy deals in the Balkans.
It is unclear what Ms. Guilfoyle will do now. Once a legal analyst for CNN and ABC in New York, her career at Fox ended in 2018, when two people familiar with her exit told The Times on the condition of anonymity that she had been forced to leave over questions about inappropriate workplace behavior.
The New Yorker reported two years later that Ms. Guilfoyle had been forced out because of sexual harassment allegations brought by a female assistant, including that she had showed the assistant photographs of genitalia of men with whom Ms. Guilfoyle had had sexual relations.
The magazine reported that the assistant had received a settlement of more than $4 million. Ms. Guilfoyle denied the allegations through her lawyer at the time, and declined to comment in the Times interview last year.
She was immensely proud of her ambassadorship. At the end of the interview, she pointed out a framed document near the entrance to her official residence, Jefferson House, that listed all the American ambassadors to Greece since 1948. Every one until Ms. Guilfoyle was a man.
“Here I am,” she said, pointing to her name. “I almost cried.”
Edward Wong contributed reporting.
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