Show of hands: how many of you are surprised that Kimberly Guilfoyle imploded and wound up getting herself fired from her ambassadorship?
I didn’t think so.
Guilfoyle has had “ticking time bomb” written all over her surgically enhanced face for at least the past five or six years. This U.S. Ambassador to Greece gig was never going to turn out well. It was all just a matter of what would bring her down.
Did I have “Reached out to a wealthy donor to make a $100,000 payment on her American Express Card in exchange for access to Donald Trump’s inner circle” on my 2026 bingo card? No. But it makes perfect sense that it would prove her undoing because it demonstrates she lives way above her means.
Trust me, it isn’t the corruption part that proved intolerable to the president. That’s pretty much a given for anyone on the administration staff. It’s that she doesn’t have enough money to pay off a bill many of us see as extravagant.
A quick primer on the criminality tolerance scale in Washington these days:
Sexually abusing children is totally cool.
Attacking cops and destroying the Capitol gets you a pardon.
Lacking $100K? That’s a bridge too far.
This is especially true if you also happen to be a woman. Let’s recall the fates that befell Kristi Noem, Pam Bondi and Tulsi Gabbard. What did they all have in common? Ding! Ding! Ding! That’s right. None of them are men. If Guilfoyle was named, say, Pete Hegseth or Kash Patel, she’d have skated through unscathed.
It's the fact she's female that cemented her fate.
The only things respected these days at the White House are testosterone and money, and not necessarily in that order. Just ask Pentagon Pete. If Guilfoyle made a major screw-up, it was the fact she asked Eric Deters for only $100,000 because it showed she was playing in the minor leagues. She should have hit him up for at least a million.
In Trump World, when it comes to fraud and depravity, the only rule is go big or go home. And home Kimberly went.
It’s outrageous wealth and self-enrichment that drives every single Republican. They see no other reason to seek public office, having learned at the feet of a man who has transformed the presidency into a multibillion-dollar ATM and daily enhances his personal coffers by several million more.
Just how wealthy is Trump’s inner circle? An August analysis by The Washington Post found that 57 Trump administration officials were worth at least $100 million. That includes 17 ambassadors and 40 other senior executive-branch officials. Eight of the 23 Cabinet members were also said to quality at that level.
That same August analysis found more than four times as many officials worth in excess of $100 million in Trump’s second administration as there were in the George W. Bush, Barack Obama and Joe Biden administrations combined.
Leading this financial parade are several individuals whose personal wealth exceeded $1 billion, including Commerce Secretary Howard Lutnick ($7.3 billion), Deputy Defense Secretary Stephen Feinberg ($6.3 billion), Education Secretary Linda “A1” McMahon ($3 billion), special envoy Steve Witkoff ($2.3 billion) and son-in-law/special envoy Jared Kushner ($1 billion).
By this yardstick, of course, Guilfoyle didn’t have two nickels to rub together. She tried to hide it behind a glamorous public image that apparently suffered some cash-flow issues. In Trump’s asking for her resignation, the question is whether he was upset that she needed money, that she apparently sought it from a donor, or that the reported texts that went back-and-forth with Devers became public.
The thing is, I’m kind of feeling sorry for ol’ Kimberly. How was she to know that the lavish gifts, luxury hospitality and preferential treatment she received as an ambassador didn’t just go with the job? She had evidently never received a single indication that her ethics mattered in the slightest. From the behavior of everyone around her, she came to believe that having her every desire satisfied was just a perk of the position.
What is a foreign ambassador even supposed to do if not pillage booty and act like a big shot? The job description is already a little murky. If she was supposed to serve as Trump’s principal diplomatic representative in Athens, that should mean behaving precisely as Trump would have if he were there.
Some might therefore observe that Guilfoyle succeeded on every level. As her boss taught her, she is said to have taken everything that wasn’t nailed down. How was she to know that asking someone to pay her bills and keep it quiet so no one finds out about it was wrong?
When she was nominated for the Greece post in December 2024, shortly after Trump’s win, the timing suggested two things:
1. She was a longtime Trump loyalist who had earned this plum assignment.
2. Trump needed to ship her to live on a different continent because his son Donald Trump Jr. had just dumped her as his fiancée and he’d taken up with a new fiancée.
My guess is that Guilfoyle wasn’t given much in the way of instruction on her way out of the country. It was probably something like, “Here’s your plane ticket. Here’s where you’ll live. Enjoy!”
The woman can’t be faulted for taking her assignment to mean that she could treat the country as her own personal gifting suite.
And I mean, what kind of world has it become when a U.S. diplomat can’t behave like a common white-collar criminal and get away with it? It’s utterly disheartening.
Some might observe that Guilfoyle’s little financial predicament was exposed precisely because she was attempting to maintain her place in a political world dominated by people with vastly greater means. The poor lady was merely trying to keep up with the Lutnicks, and look at where it landed her.
Next time Guilfoyle needs help paying off a six-figure bill, I’d be happy to help launch her GoFundMe. It’ll prove much less messy in the long run.
(Ray Richmond is a longtime journalist/author and an adjunct professor at Chapman University in Orange, CA.)