AMBASSADORIAL DISFUNCTION

Kimberly Guilfoyle’s Greek Tragedy Is How Every Trump Story Ends

The best may be yet to come, but the worst certainly already happened.

Opinion

The knives had been out for Kimberly Guilfoyle for some time. Her appointment as ambassador to Greece last year was widely seen as a White House scheme to get her out of the country after her breakup with Donald Trump Jr. But now it seems she was running a scheme of her own: The Wall Street Journal broke the story of her begging Trump donor Eric Deters to pay off a $100,000 Amex bill at the time of her confirmation, alongside a blistering critique of her jet-setting lifestyle.

It’s not a good look just weeks before the midterms when the cost of living is a top-line voter concern. Guilfoyle’s shakedown dominated the news cycles and forced Trump’s ever-bruised hand into asking her to resign. He left his new press secretary to deliver the verdict on live TV during her first briefing—a performance, by the way, which left many assuming her pink slip isn’t far away either.

Trump then quickly tried to distance himself, telling reporters who had dared suggest Kimberly was basically a member of the family that she had “only dated his son a long while ago.” (That relationship with Don Jr. lasted through 2024, and she was his fiancée.)

But convincing voters this is an isolated incident is a hard sell; Deters called Guilfoyle’s dealings “pay to play,” which seems like common practice in an administration that is transactional from the top down.

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The notion of an entitled Trump appointee shaking down a donor and living high at taxpayer expense rubs people across the political spectrum the wrong way. Even worse from Trump’s point of view, it shines the spotlight brighter on himself and his family’s self-enrichment: Trump is $2.2 billion dollars richer than he was when he took office last year, and Don Jr.’s business dealings with Saudi Arabia or any number of crypto firms, meme coins, and corporate boards are front-page news. The First Lady got in on the fun too with a “Melania” book and a “Melania” documentary, widely panned but funded and boosted by Amazon. She also has a line of collectibles and a crypto coin.

Aside from Melania, this administration is particularly hard on its women: Kristi Noem, Pam Bondi, Tulsi Gabbard, and the Secretary of Labor whose husband was locked out of the building for allegedly sexually harassing workers. Yes, all made their misdeeds; they are not women I would go to bat for. But how many of Trump’s men can you name who’ve been treated in the same manner?

FBI Director Kash Patel has weathered multiple egregious scandals but still has his job, and Trump lets RFK Jr. “go wild on health,” despite, well, pick your poison. Pete Hegseth should also have been removed a long time ago for a variety of reasons, but the boys all keep their jobs—Hegseth’s including plans for a literal firing squad—while the girls get fired.

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Kimberly Guilfoyle’s Desperate Effort to Save Job Is Leaked

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Cutting Guilfoyle loose is not without risk. But she’s the sacrificial lamb because her grift is both audacious and easily understood. Everybody has credit cards, and most of us would love a little help paying down an overdue balance once in a while. But few of us have the opportunity to text a contact, “Honey, please, I need you to get this done for me today”—”this” being a six-figure payment—along with instructions to wire the money so it can’t be tracked. Still, an AMEX bill doesn’t have the mystery of insider trading or the grime of $50,000 in cash proffered in a takeout bag. What Guilfoyle did is corruption for dummies, an infraction that was a little too close to home.

“This is a clear example of something that’s done routinely,” explained Will Ragland, who tracks government corruption at the liberal think tank Center for American Progress. “She got caught, and they had to do something about it… They’re worried this will open a can of worms when a new Congress comes in to do oversight because this is one piece of a larger puzzle.”

And many of the people holding pieces of that puzzle are more than prepared to use them as insurance. Or as weapons. One hallmark of this administration is that it’s a snake pit—Trump wouldn’t have it any other way. Many of the insiders hate each other, and have for a long time. Faced with a losing hand in the midterms, they do what politicos do: they turn on each other. Guilfoyle has enemies dating back to when she was a prosecutor in San Francisco and married to the city’s then-mayor, Gavin Newsom. She also has press contacts she can use to paint a damning picture of her former colleagues if she chooses the ‘burn book’ route. Perhaps even the threat of it is enough.

That’s why Trump, even having shown her the door, will likely take pains to contain the fallout. “They will have to work hard to take care of her, keep her on a tight leash,” Ragland told the Daily Beast, noting that Guilfoyle was “also a significant fundraiser for all things Trump.”

In Trump world, everything is a transaction, and at the end of the golden brick road awaits a pardon should Guilfoyle need it—a powerful incentive to swallow her pride and accept Trump’s terms.

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Eleanor Clift

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