Kimberly Guilfoyle has another “ex” to add to her long list.
The Maga stalwart – former ambitious San Francisco attorney, former first wife to then San Francisco mayor Gavin Newsom, bitter rival of Kamala Harris, Fox News star, influential Republican Party fundraiser and ex-fiancée to Donald Trump Jr – is closing another chapter on her resume. She is now also no longer Donald Trump’s ambassador to Greece.
The 57 year-old has never spent long out of the headlines: from her “scream speech” at the 2020 Republican convention in a trademark red dress, to glamorous parties and deal-making in Athens, to a “honey” text message that may have been the last straw that triggered her dismissal.
An embattled Trump has finally cast her adrift, confirming on Tuesday the earlier announcement by his new press secretary that Guilfoyle had been asked to resign, and dismissing her as someone who “I guess, dated my son a long time ago” (Guilfoyle and Don Jr broke off their engagement just two years ago).
Guilfoyle is defiant. In a long social media post she said the ambassador job had been the “honour of my life” and addressed “the recent allegations against me”, without identifying which she was referring to.
“I will not allow false accusations to define my decades of public service,” she said. “These allegations are false, and I intend to vigorously defend my name, my reputation, and my integrity.”
Trump was brief when asked why Guilfoyle was gone. “I didn’t like what I read,” he said.
‘The American dream’
Guilfoyle is possibly best-known for her address to the 2020 Republican convention, which became known as the “scream speech” as it was delivered at top volume to a room that the Covid pandemic had left as an empty void.
Dressed in clinging Nancy Reagan-red, the then-chairwoman of the Trump Victory Finance Committee proclaimed: “My mother, Mercedes, was a special education teacher from Aguadilla, Puerto Rico. My father, also an immigrant, came to this nation in pursuit of the American dream. Now, I consider it my duty to fight to protect that dream.”
In a twist of fate, another star-in-a-red-dress from that 2020 convention, Natalie Harp, who herself has recently weathered controversy, would likely have handed Trump the printouts that just ended Guildfoyle’s career.
Guilfoyle reprised her famous 2020 Republican National Convention appearance in 2024 (Photo: J Scott Applewhite/AP)Guilfoyle’s story is one of hard-won success, punctuated by big setbacks. She was just 11 when her mother died of leukemia. She paid her tuition at law school by modelling, and rose to prominence as a young lawyer in San Francisco – a contemporary of Kamala Harris – winning international attention when she prosecuted the bizarre case of a woman mauled to death by a dog.
In 2001 she married rising Democrat star Newsom, and they were briefly the political power couple of the state (their honeymoon was, ironically, to Greece). But her jump to television – Court TV, CNN, ABC, then Fox News – reoriented her career to New York. They divorced in 2006.
Her 12 years as co-host of Fox afternoon panel show The Five came to an abrupt end in 2018, amid serious allegations of inappropriate workplace behaviour, which she publicly denied.
‘You feel like you have a calling’
Guilfoyle seamlessly segued to become one of Maga’s shining stars, making speeches and running fund-raising for Trump Victory, his main campaign organisation.
Her shift into politics had been under way for a while. While at Fox she began dating Don Jr and was briefly in the mix to become White House press secretary, telling one newspaper: “I’ve never been someone who’s motivated by financial interests… if you’re passionate about it and you feel like you have a calling for anything in life.”
Don Jr proposed on New Year’s Eve 2020 and they bought a home together in Florida. They exchanged loving messages on social media: “Falling in love with my fiancé more and more every day,” Guilfoyle posted on Instagram on Valentine’s Day 2022. “Thanks for always being there no matter what the haters are throwing our way,” he said in 2024.
But in December 2024 the Daily Mail published photos confirming rumours that Don Jr had broken off the engagement and was dating socialite Bettina Anderson, whom he married in May this year.
Mere hours after the photos hit the headlines, the President made an announcement on Truth Social: “Today, I am very pleased to announce the appointment of Kimberly Guilfoyle as the United States Ambassador to Greece,” the then President-elect said.
“For many years, Kimberly has been a close friend and ally. Her extensive experience and leadership in law, media, and politics along with her sharp intellect make her supremely qualified.”
A spokesman for Trump told The New York Times that suggestions that Guilfoyle’s nomination was related to her relationship with Don Jr were “very sexist”.
Parties and power
After a long wait for a Senate confirmation, that eventually arrived in September last year, Guilfoyle hit Athens with a bang.
She reportedly arrived on the private jet of a multimillionaire Greek American businessman.
Wielding her impeccable access to the heart of the White House, she was suddenly everywhere. Everyone wanted to meet her, and she successfully pushed – as she promised in her confirmation hearing – deals aimed at weaning Europe off reliance on Russian oil (and opening doors for American interests).
Guilfoyle made waves as the US ambassador in Athens (Photo: Mark Schiefelbein/AFP)Thanks to her millions of Instagram followers, glamorous selfies and trips to fashion shows, nightclubs and art galas, she was also catnip to the local media, trailed by the paparazzi, beloved by the gossip shows – she even featured on the cover of Vogue Greece.
The opposition’s complaints about “transactional diplomacy” made little impact.
Downfall
Rumours swirled about her, and eventually surfaced in the media.
The Wall Street Journal was on her tail over her close association with Greek energy tycoons, asking questions about whether her approach was one appropriate to the post of ambassador, including claims she was accepting gifts of trips on their private jets. The embassy said she had “faithfully followed [government] ethics and gift reporting guidelines”.
The Daily Mail gleefully tracked her lavish lifestyle, parties and expenses, at one point alleging an incident where she demoted a security officer for not supplying fresh ice cubes late at night.
The final blow came late last week, when the WSJ reported the claims of US businessman Eric Deters. Deters alleged that Guilfoyle had offered access to Trump administration officials for money, and just days before her Senate confirmation hearing had asked him to pay a $100,000 (£753,500) American Express bill.
In a blitz of media interviews Deters repeated the allegations, offering what appeared to be text messages from Guilfoyle to substantiate them.
“Honey please, I need you to get this done for me today,” she had allegedly written, adding a prayer emoji, according to multiple US media organisations to whom Deter showed the messages.
Deter claimed that Guilfoyle promised him access to Trump administration officials as a “quid pro quo”.
He said he refused to pay her credit card bill, as he “didn’t have that money at the time”.
Guilfoyle’s lawyers denied that she had done anything wrong, disputed the authenticity of the messages, and said the money she was seeking from Deter was proper payment for public appearances and speaking engagements that predated her ambassadorial nomination.
“I have dedicated my professional life to fighting for justice, standing up for what is right, and defending the values that make America exceptional,” Guilfoyle said, in her resignation tweet.
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