As would seem fitting, Kimberly Guilfoyle’s fiancé Donald Trump Jr. spearheaded the rush to congratulate her upon the announcement of her unexpected selection as Ambassador to Greece this week.
‘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 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, definitely not since this week’s extremely public displays of ‘moving on’.
First Don Jr, 46, was photoed 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 conjecture about the condition of their relationship – not to mention the Mail’s images of Don Jr smooching the new woman in September – even twice-married Guilfoyle must indeed realise it’s over. A formal announcement is awaited.
A 55-year-old Maga-loyalist and former Fox News panellist noted for big hair and tight clothes, Guilfoyle claims to have been ‘blindsided’ by Don Jr’s new romance.
Some claim that the relationship has been in crisis for a long time.
Insiders claim that when Guilfoyle invited hundreds of people to her 55th birthday celebration at their Jupiter, Florida, home in March, tensions were already evident. There have been allegations that Don Jr. disappeared for a portion of the evening, seemingly withdrawing to his bedroom.
Others suggest Don Jr has found himself increasingly embarrassed by Guilfoyle’s little-left-to-the-imagination wardrobe, colourful public displays and her preference for a party lifestyle that might sit awkwardly with the Trump family increasingly mindful of its presidential legacy.
According to one former coworker at Fox News, the lawyer-turned-activist was known as ‘the Margarita girl’ thanks to her fondness of the popular cocktail and party lifestyle associated with it.
Although there is no indication that Guilfoyle regularly consumes excessive amounts of alcohol, the Trumps are undoubtedly sensitive to it.
Don Jr. is well-known for taking his sobriety very seriously because he drank his way through college. Ivanka, his sister, abstains from drinking.
As a result of his older brother Fred Jr.’s death from alcoholism at the age of 42, their father Donald is well-known for being a teetotaller.
Many will remember 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 definitely sociable.
A high-ranking Trump official told the Mail that she would be perfectly suited to the life of an ambassador, which includes meeting, greeting, and hosting events.
However, the Trumps might not be totally comfortable with Guilfoyle’s flamboyance.
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 speculate that their issues may go beyond party etiquette and short skirts.
For Guilfoyle’s undeniable drive and ability, insiders suggest that her approach to relationships might appear overwhelming – and that her younger partner sometimes 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.’
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 employed were instructed 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.
In 2011, she joined Fox’s primetime panel show ‘The Five’. Washington Post has reported that she was assigned ‘the leg chair’ at 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 dedicated supporter of Trump after he announced his 2016 candidacy. She 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.’
Despite her success at Fox, Guilfoyle’s image began to deteriorate in the summer of 2016 when she mobilised women to protect Ailes’s reputation following his sexual harassment allegations.
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, who was also 17, and the two parents grew close.
Guilfoyle and Don Jr. made their relationship public in May 2018.
Although she has consistently insisted that she left Fox because she wanted to be more active in the initial Trump campaign, the New Yorker revealed in 2020 that there were far more serious accusations involved.
It is believed Fox had to pay an assistant more than 4 million dollars after she ‘alleged that Guilfoyle, her direct supervisor, subjected her frequently to degrading, abusive, and sexually inappropriate behaviour.’
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’.
The accusations have been refuted by Guilfoyle.
She pushed herself into Trump’s campaign after leaving Fox, and the Republican party soon embraced her. She passionately praised Trump in talks at conservative gatherings and rallies.
With her political career on the rise, she acted as Trump’s spokesperson at rallies nationwide, establishing a reputation as someone who would stop at nothing to support him.
Guilfoyle was appointed chair of the finance committee for the Trump Victory Committee in 2020 and gave an infamous address at the Republican National Convention which was variously described as ‘impassioned’ or ‘unhinged’.
She was in similar shouty form at this year’s Republican Convention in Milwaukee.
On December 31, 2020, Guilfoyle and Don Jr. became engaged, although they didn’t tell anyone until 2022.
In the meantime, they purchased two homes together: one in Florida that they made their primary residence and another in the Hamptons which they eventually sold.
However, pictures of Don Jr. canoodling with Bettina Anderson, a woman, during brunch in Palm Beach surfaced in September 2024.
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 revealed, 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.’
Since posting photos from a Mar-a-Lago party on November 14, Guilfoyle has not been spotted on Don Jr.’s arm.
Senior Republicans have been supporting Guilfoyle despite—or maybe because of—the unfortunate conclusion to her relationship with Don Jr.
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.’
Bettina Anderson, therefore, started an affair with someone who was in a well-known and committed relationship. Not good news for the future, not forgetting that the person in that relationship is the cheater. Bettina needs to remember that if they cheat once, they’ll do it again, and cheaters don’t leave for someone better, they leave because it’s their tiny ego that needs stroking and presumably something else that is tiny too.
Don Jr was not committed to the relationship, but then he’s not married to Kimberly so can do what he wants.
If they do it with you, they’ll do it to you. Bettina had best sleep with one eye open. It’s a disgraceful way to start a relationship.
Don Jr obviously pursued Kimberly because of her ‘little left to the imagination’ wardrobe, but will he claim that’s why he left her or the fact that he has a roving eye and being faithful is challenging for him? If he doesn’t want to be with Kimberly, don’t destroy her reputation, it’s not an appealing quality.
THE MONTHLY MOSQUITO 