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Donald Trump Jr’s phantom engagement leaves Americans baffled

If a power couple splits, but everybody ignores it, did it ever really happen? That’s the question being posed, today, in Donald Trump’s orbit.

‘Choice between safety and chaos’: Kimberly Guilfoyle’s Trump re-election pitch

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If a long-term power couple splits in MAGA-world, but everybody involved ignores it, did it ever really happen?

This, we must ask, upon hearing the simultaneously tragic and happy news that former TV host Kimberly Guilfoyle – who is still, as far as we know, engaged to Donald Trump’s eldest son Donald Jr – has been picked to be the next US ambassador to Greece.

The news came, today, in an announcement that coincided so very curiously with the revelation that Donald Jr had been holding hands and otherwise hobnobbing, in public and in conspicuously affectionate fashion, with a Florida socialite who is very much not his fiancee of almost four years.

That socialite, Bettina Anderson, has previously been seen hanging around Mr Trump’s Florida resort, Mar-a-Lago – generally quite an efficient way to meet members of the Trump family, if one is so inclined.

Look, whatever the Trump clan’s charms, and I’m assured they exist by a great many people, fidelity is not among them. Don Jr’s daddy cheated on all three of his wives. Don Jr was less than faithful to his first wife, Vanessa, whom he divorced in 2018.

Don Jr and Kimberly Guilfoyle at a Trump press conference in 2023. The pair have, at least officially, been engaged since 2020. Picture: Chandan Khanna/AFP
Don Jr and Kimberly Guilfoyle at a Trump press conference in 2023. The pair have, at least officially, been engaged since 2020. Picture: Chandan Khanna/AFP

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So, the appointment. Plausible explanations for it run thin rather quickly.

Ms Guilfoyle has no apparent connection to Greece. She’s a Californian whose parents were from Ireland and Puerto Rico. And she has no diplomatic experience; her career trajectory was prosecutor, to TV personality, to Trump political surrogate (there’s a bit of overlap between those last two), to her new gig as a soon-to-be ambassador.

Don’t get me wrong: it’s a very nice job. In Ms Guilfoyle’s place, I believe I would develop a keen and immediate interest in examining the beaches of Paros. For diplomatic purposes. And in the scenario of my current marriage collapsing, I probably would accept a high-paying job in Athens as fair compensation.

It’s also not an appointment that can do much damage. This isn’t like putting an Assad and Putin apologist in charge of America’s intelligence agencies, or a TV talking head in charge of the three-million strong US military, or an anti-vaxxer in charge of the health system. That would be preposterous! Who would even conceive of such nonsense?

(Oh. Right.)

Ms Guilfoyle will presumably head off to Greece, have a lovely time, and come back in four years with an enviable tan and the two countries’ bilateral relationship essentially unchanged.

Ms Guilfoyle speaking at this year’s Republican National Convention. Picture: Andrew Caballero-Reynolds/AFP
Ms Guilfoyle speaking at this year’s Republican National Convention. Picture: Andrew Caballero-Reynolds/AFP

We have two problems here, though. One, Ms Guilfoyle has none of the qualifications or expertise required to be a senior diplomat. She spent several years saying nice things about the President-elect on TV, and campaigning for him, and that’s about it. Her former legal career, as a Californian prosecutor, may have qualified her for some sort of role in the Justice Department. Maybe. This ain’t that.

She’s certainly qualified to go on holiday to Greece, and to stay in far nicer hotels than the rest of us. (The qualification here is money. She has a lot of it. That is a common theme in Trump-world.)

In fairness this lack of a relevant resume is not, in itself, an unusual departure from Mr Trump’s normal hiring criteria. Being telegenic is right up there with loyalty and annoying the proper folks on the left as his top desired traits, while knowledge of the field tends to be down near the bottom, along with any sort of flair for independent thought.

Two, you cannot escape the sense that Ms Guilfoyle is being thrown a mid-level but quite comfortable job in the new Trump administration to get her out of the proverbial picture, and avoid any awkwardness as Don Jr moves on with his new girlfriend.

That is what turns this otherwise private matter into public business.

Is there any universe, in which Ms Guilfoyle didn’t date Mr Trump’s son, where he would have picked her to be an ambassador? Not to mention the fact that her destination may as well have been chosen by chucking darts at a map.

From right to left: Donald Trump Jr, Kimberly Guilfoyle, Tiffany Trump and her husband Michael Boulos, all on stage during Mr Trump’s election night victory speech. Picture: Jim Watson/AFP
From right to left: Donald Trump Jr, Kimberly Guilfoyle, Tiffany Trump and her husband Michael Boulos, all on stage during Mr Trump’s election night victory speech. Picture: Jim Watson/AFP

The statements from Mr Trump, Don Jr and Ms Guilfoyle today were bizarre. Bizarre! All three of them spoke as though the engagement between Don Jr and Ms Guilfoyle, dating back to the end of 2020, never existed.

“Today, I am very pleased to announce the appointment of Kimberly Guilfoyle as the United States ambassador to Greece,” Mr Trump wrote on his social media platform, Truth Social.

“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 to represent the United States and safeguard its interests abroad.

“Kimberly is perfectly suited to foster strong bilateral relations with Greece, advancing our interests on issues ranging from defence co-operation to trade and economic innovation.

“Congratulations Kimberly!”

Yes, congratulations, woman who almost became my daughter-in-law. I’ve given you the same basic treatment, in this statement, as the rando I chose to be deputy treasury secretary.

Donald Trump. Picture: Allison Robbert/AFP
Donald Trump. Picture: Allison Robbert/AFP

Next we have the statement from Don Jr.

“I am so proud of Kimberly,” he said.

“She loves America and she always has wanted to serve the country as an ambassador. She will be an amazing leader for America First.”

OK, bit more of a personal touch there. Is she still your fiancee though, mate?

“I’m honoured to accept President Trump’s nomination to serve as the next ambassador to Greece and I look forward to earning the support of the US Senate,” Ms Guilfoyle herself said on social media.

“President Trump’s historic victory is bringing hope and optimism to the American people and to freedom-loving allies across the world.

“It was the democratic values born in Greece that helped shape the founding of America. And now we have an opportunity to honour that history by bringing about better days here at home and abroad.

“As ambassador, I look forward to delivering on the Trump agenda, supporting our Greek allies, and ushering in a new era of peace and prosperity.”

Yes, good, fine, I’m sure the Greek people will be thrilled. Is anybody going to mention the phantom engagement? Or shall its name never be spoken again? If we don’t talk about it, can we just go on with life pretending it never happened at all?

Ms Guilfoyle and Don Jr back in 2020, before their engagement. Picture: Jim Watson/AFP
Ms Guilfoyle and Don Jr back in 2020, before their engagement. Picture: Jim Watson/AFP

The subtext, here, is that Don Jr has become the most politically engaged of Mr Trump’s children. (I say children; he’s a 46-year-old man. And yet the label fits.)

We all endured a gazillion thinkpieces throughout 2016, and for a few years afterwards, about Ivanka Trump, and how she was the heir-apparent to her father’s political empire.

After all, she was the one who got prime speaking gigs at the major Republican political events, and a frustratingly nebulous role as some sort of White House adviser, and she was the one whose husband got to enrich himself the most during Mr Trump’s first term, using his gig as a negotiator in the Middle East to get cozy with the Saudis and so forth.

That narrative was all wrong, though. Ivanka never got her father’s brand of politics, and she could never have inherited it. In fact she actively resisted it.

She was a media darling because of the delusion, which persisted for years, that she could moderate Mr Trump, and tug him back towards his roots as a pro-choice Democrat, which is what the Trumps basically were before the Obama years.

Don Jr, meanwhile, was quietly working away in the background, building his credibility as the true heir to Trumpism. He’s confrontational. He’s all-in on the culture wars. He publishes freewheeling bro-casts, and posts tweets nakedly trolling the left, and indulges in all the best conspiracy theories. On an almost primal level, he understands his father’s political appeal.

Which is why a poll this week found Don Jr was tied with the soon-to-be vice president, J.D. Vance, as the leading candidate for the next Republican presidential nomination.

Donald Trump on stage, during the campaign, with his children Tiffany, Eric and Don Jr (also Tiffany’s husband, who is not very relevant). Picture: Charly Triballeau/AFP
Donald Trump on stage, during the campaign, with his children Tiffany, Eric and Don Jr (also Tiffany’s husband, who is not very relevant). Picture: Charly Triballeau/AFP

This man is not a sideshow anymore. He is someone who, far-fetched as it seems, could have a plausible shot at winning the presidency. So if he’s fobbing off his fiancee by getting daddy to give her a glitzy taxpayer-funded job overseas, that isn’t just entertainment rag gossip; it becomes a genuine data point in judging the character of the guy.

Ms Guilfoyle herself said it best, perhaps, during her deeply strange Republican National Convention speech in 2020. Her words now reek of an unsettling prescience: “THE BEST. IS YET. TO COME!!!”

She was right, albeit prematurely, regarding Mr Trump. She might be right about Don Jr, too. And she was most certainly right about her own fortunes. Given the choice between life as a Trump groupie, haunting the halls of Mar-a-Lago, or as someone who spends her weekends exploring the Greek islands, she’s done OK, in the end.

Twitter: @SamClench

Originally published as Donald Trump Jr’s phantom engagement leaves Americans baffled

Read related topics:Donald Trump

Original URL: https://www.dailytelegraph.com.au/lifestyle/relationships/donald-trump-jrs-phantom-engagement-leaves-americans-baffled/news-story/55548031f75a38b4f9d6018222758527