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When Kimberly Guilfoyle’s two-year engagement to Donald Trump Jr imploded late last year, it presented the new president with a tricky problem.
Forget affairs of state and signing radical executive orders. He had to decide how best to minimize the fallout from his son’s very public dumping of the Maga-loyalist and former Fox News presenter for a much younger Palm Beach socialite and model.
Then in December, Trump Sr unveiled what appeared to be a masterstroke with the shock announcement that 55-year-old Guilfoyle was his pick for US Ambassador to Greece.
It was the perfect solution.
Reward Guilfoyle for her rabid devotion to the Trump cause with a shiny new job in one of Europe’s most popular capitals, while at the same time moving her thousands of miles and several time zones away from her ex, Don Jr, and his new girlfriend Bettina Anderson, 38, in Florida.
And indeed, everyone was pleased.
‘I am so proud of Kimberly,’ Don Jr, 47, gushed after the news broke.
Guilfoyle, meanwhile, no doubt envisaging her glamorous new life as a top diplomat in Athens – and perhaps, as a newly-single woman, encounters with eligible Greek tycoons – added: ‘I’m honored to accept President Trump’s nomination.’
Kimberly Guilfoyle, 55, is heading off to her new life in Athens as the US Ambassador to Greece. But experts have told the Mail that the role may not be the luxurious, romantic lifestyle she imagines, as it comes with a major downside.
But insiders have now told the Daily Mail that this seemingly happy conclusion comes with major caveats.
The ambassadorship is not quite as cushy or glamorous as it seems, and is accompanied by the unique risk of international scandal.
Insiders warn that Guilfoyle can expect a lifestyle that’s a lot less luxurious than what she was used to with Don Jr during their 6-year relationship. And it will require the ‘Margarita Girl’ – as one former Fox News colleague dubbed her because of her apparent love of the cocktail – to be on her best behavior and to keep her guard up at all times.
As the Daily Mail reported last year, it’s claimed that Guilfoyle’s party-loving persona and penchant for form-hugging and revealing fashion, were part of the reason that Don Jr called time on the liaison.
‘She will always be on duty, she’s always news, she’s always a photo opportunity to the Greek press. She will be under continuous review,’ a former private secretary to a senior member of the British Royal Family with experience of diplomatic missions told the Daily Mail.
Despite her successful career as a public attorney in San Francisco and LA before her TV role and political activism intervened, Guilfoyle isn’t known for her diplomacy.
In fact, plain speaking and outrageous comments are part of Brand Kimberly. And she certainly hasn’t endeared herself to the Greeks in the past.
In 2015, when she was a co-host on Fox News’s The Five and Greece was still reeling from the fallout of the catastrophic 2008 economic crash from which it had to be bailed out three times by the IMF, she dismissed the Greek people as ‘freeloaders’ and accused them of ‘retiring too early’.
‘It doesn’t matter if you made great yogurt. I don’t care,’ she quipped.
Kimberly will be mistress of Jefferson House, a stately villa in the exclusive Kolonaki neighborhood of Athens, complete with a tennis court and swimming pool, but it doesn’t compare to the 11,000-square-foot luxury mansion she shared with Don Jr in Jupiter, Florida.
‘It’s a big old house, in the middle of Athens about a block from the Embassy. It’s early 1900s and it takes a lot of maintenance,’ former US Ambassador to Greece, Thomas Miller, told the Mail.
But it seems there will be an exciting party scene on her doorstep, from exclusive bars and clubs frequented by European elites to more relaxed tourist hotspots, where Kimberly can let her hair down.
No doubt she’ll overcome that faux pas but sources have warned that Guilfoyle will quickly realize the role comes with other downsides.
Yes, she will be mistress of Jefferson House, a stately villa in the exclusive Kolonaki neighborhood of Athens, complete with a tennis court and swimming pool, but it doesn’t compare to the 11,000-square-foot luxury mansion she shared with Don Jr in Jupiter, Florida.
‘It’s a big old house, in the middle of Athens about a block from the Embassy. It’s early 1900s and it takes a lot of maintenance,’ former US Ambassador to Greece, Thomas Miller, told the Daily Mail.
And, as ambassador, you’re not allowed to bring any home comforts such as your own furniture, Miller reveals.
However, Miller adds that, in a break from tradition, he’s ‘heard secondhand that she might want to bring some of her own staff out with her and no one that I’m aware of has ever done that.’
Putting aside the excessive scrutiny she’ll be subjected to, the attention of the paparazzi and the drawbacks of her new lodgings, what else can fun-loving Kimberly Guilfoyle expect from her Athens sojourn?
It seems there will be an exciting party scene on her doorstep, from exclusive bars and clubs frequented by European elites to more relaxed tourist hotspots.
‘There’s a well-established Athens social scene and she will be expected to participate in it fully and to entertain regularly,’ the ex-Royal private secretary said.
The role also means Kimberly will be living thousands of miles away from her former fiance, Don Jr after their relationship and two year engagement crumbled last year.
And it means Don Jr will be free to relax in Florida in the company of his new girlfriend, younger model and socialite Bettina Anderson, 38 (pictured).
Kimberly will have the chance to make plenty of new friends in her role. Former ambassador Miller says she’s expected to arrive in early summer, just as the party season is kicking off but before it gets too hot, and will find herself ‘the most popular person in Greece’.
One Greek socialite told the Daily Mail that there are a few hotspots where the Athens glitterati gather, such as the rooftop of the Hotel Grande Bretagne, with its sweeping view across the capital to the Acropolis and its Michelin-starred restaurant, frequented by actors and celebrities.
And Kimberly won’t be short of friends. Miller says she’s expected to arrive early summer, just as the party season is kicking off but before it gets too hot, and will find herself ‘the most popular person in Greece’.
But that popularity is a double-edged sword, he warns. ‘You’ve got to be careful. Everyone wants to be your friend, but she has to beware.’
This may be a challenge for the ‘Margarita girl’ and mother of one who likes to let her hair down whenever the opportunity arises.
While there is no suggestion that Guilfoyle routinely drinks to excess, ‘any diplomat who can’t hold their liquor is a liability,’ the ex-private secretary cautions.
And of course, not everyone she meets will wish the best for her, they add: ‘There will be people out there to see if she’s just there because of her connections and her pouting lips.’
But the new role is not all bad news for twice-divorced Kimberly – before her political conversion she was married to Gavin Newson, now the Democratic Governor of California, between 2001-2006, and then to businessman Eric Villency, until 2009.
Greece may also prove a happy hunting ground when it comes to finding herself a new Prince Charming. She has a few royal, options, like Prince Constantine Alexios, 26, (pictured with former girlfriend Brooks Nader) who is considered one of the most eligible men on the planet.
Or his younger brother, the dashing Prince Achileas, 24, though admittedly they may be more transitional boy-toy material than long-term prospects for Kimberly.
In the wake of her recent heartbreak over Don Jr, Greece may prove a happy hunting ground when it comes to finding herself a new Prince Charming. Indeed, if she’s so inclined, she has a few, quite literally royal, options.
The monarchy in Greece was abolished in 1974, but members of the Greek royal family are still held in high regard socially and have close connections to other European royals, not least the British Royal Family.
The late Queen Elizabeth II’s husband was, after all, born Prince Philip of Greece and Denmark.
Several Greek princes are currently on the market.
Take Prince Constantine Alexios, 26, who is considered one of the most eligible men on the planet. Or his younger brother, the dashing Prince Achileas, 24. Admittedly they may be more transitional boy-toy material than long-term prospects for Kimberly, but she’s a striking looking woman with her mane of dark hair and beguiling smile, so we shouldn’t rule out her catching a regal eye.
However, Guilfoyle may prefer to cast her eye over the next best thing to royalty in Greece – and with far more financial potential: shipping magnates.
Despite the nation’s economic travails, there are currently an estimated 12 shipping billionaires in Greece, more than at any other time in history.
‘She could snag herself the next Aristotle [Onassis],’ jokes the ex-Royal private secretary.
Given President Trump’s aggressive stance on Nato and his fury with European nations that he says fail to pay their way on defense, Guilfoyle will have her work cut out.
Or Guilfoyle’s head may be turned by one of the many top military officers she’ll be meeting and greeting on her official visits to the multiple bases dotted around the country.
‘There’s a very important naval base in Crete, [and] there’s a number of Nato facilities in Northern Greece,’ said former ambassador Miller, ‘I’d expect her to go to those.’
Given President Trump’s aggressive stance on Nato and his fury with European nations that he says fail to pay their way on defense, Guilfoyle will have her work cut out – and her diplomatic skills truly tested – keeping relations civil.
As she embarks on life as a rookie ambassador, Kimberly can certainly expect ups and downs but, assuming she survives the potential pitfalls of her three-year term unscathed, there is one very definite perk she can look forward to.
‘If you have an ambassadorship under your belt, that can take you a long way in the corporate or finance world,’ the former private secretary said.
Or she could perhaps even take a run at the presidency. Watch this space!
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