When Kimberly Guilfoyle’s shock nomination as Ambassador to Greece was announced this week, the rush to congratulate her was led, as might seem appropriate, by her fiancé Donald Trump Jr.
‘I am so proud of Kimberly,’ he gushed on social media. ‘She will be an amazing leader for America First.’
Yet if Mr Trump, son of President-elect Donald, is suitably delighted, might he also be a touch relieved to hear that his girlfriend of the past six years is scheduled to spend the foreseeable future in a foreign capital several time zones distant?
Trump and Guilfoyle’s relationship is no longer what it was, certainly not since this week’s very public displays of ‘moving on’.
First Don Jr, 46, was photographed taking a glamorous Palm Beach socialite Bettina Anderson to celebrate her birthday at a restaurant. He reportedly then ‘hard-launched’ his new girlfriend at dinner at his father’s Mar-a-Lago club on Wednesday night.
After months of speculation about the state of their relationship – not to mention the Mail’s pictures of Don Jr smooching the new woman in September – even twice-married Guilfoyle must surely concede it’s over. A formal announcement is awaited.
A 55-year-old Maga-loyalist and former Fox News panelist famous for big hair and tight clothing, Guilfoyle claims to have been ‘blindsided’ by Don Jr’s new romance.
Others say the relationship has been in crisis for some considerable time.
When Kimberly Guilfoyle’s shock nomination as Ambassador to Greece was announced this week, the rush to congratulate her was led, as might seem appropriate, by her fiancé Donald Trump Jr.
Yet if Mr Trump, son of President-elect Donald, is suitably delighted, might he also be a touch relieved to hear that his girlfriend of the past six years is scheduled to spend the foreseeable future in a foreign capital several time zones distant? (Guilfoyle is pictured at NYFW in 2019).
First Don Jr, 46, was photographed taking a glamorous Palm Beach socialite Bettina Anderson (left) to celebrate her birthday at a restaurant. He reportedly then ‘hard-launched’ his new girlfriend at his father’s Mar-a-Lago club on Wednesday night.
There were already signs of tension back in March, say insiders, when Guilfoyle invited hundreds of guests to her 55th birthday party at their home in Jupiter, Florida. Don Jr, it’s been claimed, was nowhere to be seen for parts of the evening, apparently retreating to his bedroom.
Others suggest Don Jr has found himself increasingly embarrassed by Guilfoyle’s little-left-to-the-imagination wardrobe, colorful public displays and her taste for a party lifestyle that might sit awkwardly with a Trump family increasingly mindful of its presidential legacy.
According to one former colleague at Fox News, the lawyer-turned-activist was known as ‘the Margarita girl’ thanks to her love of the popular cocktail and party lifestyle associated with it.
While there is no suggestion that Guilfoyle routinely drinks to excess, alcohol is certainly a touchstone for the Trumps.
Don Jr, having drunk his way through college earlier in life, is known to take his sobriety very seriously. His sister, Ivanka, avoids alcohol.
Their father, Donald, is famously a teetotaler – a reaction to the alcoholism which claimed the life of his older brother, Fred Jr, at the age of just 42.
Many will recall a scene first broadcast in a 2010 Larry King show in which Trump is shown instructing his son, Barron, then aged four, to avoid drugs, alcohol, cigarettes – and tattoos!
There’s no sign that she’s inked, but Guilfoyle is certainly sociable.
One highly placed Trump source told the Mail that life as an ambassador – meeting, greeting and hosting functions – would suit her well.
Yet Guilfoyle’s flamboyance might not entirely suit the Trumps.
According to People magazine, a source close to the family believes Don Jr’s new lover, 38-year-old Bettina, will be a ‘better fit’.
‘Don Jr has always wanted to look good in his father’s eyes,’ said the source.
‘Someone like Bettina, who is and has been a model, and is in Waspy circles of Palm Beach is something that would impress him.’
Another source reportedly confirmed that Don Jr dislikes Guilfoyle’s wardrobe: ‘The tight dresses need to go, and she has been told that.’
Others suggest their problems might extend beyond short skirts and party etiquette.
For Guilfoyle’s undoubted drive and ability, insiders suggest that her approach to relationships might seem overwhelming – and that her younger partner occasionally found this ‘suffocating’.
‘Don Jr came to find her a little controlling,’ said one source. ‘She started taking over – his arrangements and so on.
‘She even described herself as his Mamacita – little Mama – which gives you an idea. At first, he might have liked the fact that someone was taking care of him. But it didn’t last.
‘She’s also amazingly ambitious. Don Jr is a smart guy and very right wing, but he’s not so bothered about power. He needs some freedom.
‘He wants to spend his time hunting and fishing. But for Kimberly, it’s about power, power, power!
‘Kimberly said early on that she would try to be exactly the girl that Don wanted and seemed happy to tell people that she was the next Mrs Trump even when they’d just started dating.
‘She even went hunting with him – in full make-up, of course. But the idea that she was really into all that outdoorsy stuff faded.’
A 55-year-old Maga-loyalist and former Fox News panelist famous for big hair and tight clothing, Guilfoyle claims to have been ‘blindsided’ by Don Jr’s new romance.
‘She even described herself as his Mamacita, little Mama, which gives you an idea. At first, he might have liked the fact that someone was taking care of him. But it didn’t last,’ sources revealed. (Guilfoyle is pictured with rapper Lil Pump’).
Has there been a problem with Guilfoyle’s spending habits, also?
One Republican insider reports that – always meticulously presented – Guilfoyle had been laying out money for hair and makeup artists at their home in Jupiter.
But that, whenever Don Jr appeared, the beauticians she’d hired were ordered to pretend they were Guilfoyle’s friends and therefore working for free.
A lawyer by training, Guilfoyle first rose to prominence as a public prosecutor in San Francisco and Los Angeles.
From 2001-6, despite her later switch to the Republican cause, she was married to Democratic politician Gavin Newsom, now governor of California.
In 2011, she joined Fox’s primetime panel show ‘The Five’. Washington Post has reported that she was assigned ‘the leg chair’ on the end of the row because it would allow the audience a full view of her lower half.
It is said that Fox chairman Roger Ailes saw an image of the set-up and commented ‘there’s Kimberley, doing her job’.
She became a loyal supporter of Trump after he declared his 2016 candidacy, and apparently caught the notice of Don Jr, who told the Post in 2018: ‘When everyone else said that Hillary was unstoppable, Kimberly stood firmly with my father.’
Guilfoyle was successful at Fox but her reputation started to crumble in the summer of 2016 when she rallied women to defend Ailes’s reputation after he was accused of sexual harassment.
Guilfoyle was introduced to Don Jr by mutual friends at a Manhattan party. Her 17-year-old son, Ronan, went to the same school as Don Jr’s daughter Kai, also 17, and the two parents grew close.
In May 2018, Guilfoyle and Don Jr announced publicly that they were a couple.
She has always maintained it was her choice to leave Fox claiming that she wanted to be more involved in the first Trump campaign, but the New Yorker reported in 2020 that there were much more serious allegations at play.
It is thought Fox had to pay an assistant more than $4m dollars after she ‘alleged that Guilfoyle, her direct supervisor, subjected her frequently to degrading, abusive, and sexually inappropriate behavior.’
The assistant claimed, ‘she was frequently required to work at Guilfoyle’s New York apartment while the Fox host displayed herself naked and [that] she was shown photographs of the genitalia of men with whom Guilfoyle had had sexual relations’ and she once had to ‘massage her bare thighs’.
Guilfoyle has denied the allegations.
After she left Fox, she threw herself into Trump’s campaign and quickly became a darling of the Republican party. She attended conservative events and rallies and gave impassioned speeches praising Trump.
With her political star continuing to climb, she appeared as a surrogate for Trump at events across the country, making a name for herself as someone prepared to defend him at all costs.
Guilfoyle was appointed chair of the finance committee for the Trump Victory Committee in 2020 and gave a notorious speech at the Republican National Convention which was variously described as ‘impassioned’ or ‘unhinged’.
She was on similar shouty form at this year’s Republican Convention in Milwaukee.
Guilfoyle and Don Jr got engaged on December 31, 2020, although they didn’t share the news with the public until 2022.
Meanwhile, they bought two houses together, one in the Hamptons, which they later sold, and one in Florida which they made their main home.
However, in September 2024, photos emerged of Don Jr canoodling with another woman over brunch in Palm Beach – the woman being Bettina Anderson.
One source familiar with the family told the Mail this week: ‘There is no more Kimberly and Don – at least not romantically. Their engagement hasn’t officially been called off yet. They were waiting until after the inauguration to announce.’
Speaking after Don Jr’s affair was exposed, one source told the Mail: ‘Kimberly either didn’t know about Bettina – or didn’t want to know. Did she hear whispers that Don Jr was fooling around with someone else? Probably.
‘She’s no fool but it’s easy to deceive yourself when you’re so committed to someone and believe he’s committed to you.’
Guilfoyle has not been seen on Don Jr’s arm since November 14 when she posted pictures from a party at Mar-a-Lago.
Guilfoyle was introduced to Don Jr by mutual friends at a Manhattan party. Her 17-year-old son, Ronan, went to the same school as Don Jr’s daughter Kai, also 17, and the two parents grew close.
She became a loyal supporter of Trump after he declared his 2016 candidacy, and apparently caught the notice of Don Jr, who told the Washington Post in 2018: ‘When everyone else said that Hillary was unstoppable, Kimberly stood firmly with my father.’
Despite – or perhaps because of – the disappointing end to her relationship with Don Jr, senior Republicans have been rallying to Guilfoyle.
As one pointed out, Guilfoyle will certainly ‘know where the bodies are buried’.
A source close to the Trump transition team contacted the Mail to say the nomination could be a chance, ‘to show her talents on the world stage. It’s tremendous for her, tremendous for the country and tremendous for Greece.’
A leading Trump insider told the Mail that Guilfoyle was genuinely happy to have been proposed as Ambassador to Greece – although she is yet to be confirmed in the role by the Senate.
‘She’s pleased because she’s a very sociable woman and this would suit her lifestyle, with plenty of hosting and socializing,’ said the insider.
‘President Trump has always been very keen on her. Was this her life-plan? Clearly not. But she’s a strong and intelligent woman and she’s excited for the new role.’
Besides, as Guilfoyle told The Post in 2018 – explaining her remarkable transformation from Democratic wife to Republican loyalist – she’s adaptable.
‘I am always changing and doing stuff,’ she said. ‘Grass doesn’t grow too long under my feet.
‘I’m on the move.’