After half-heartedly including some actual professionals in his first administration, Donald Trump is now served almost exclusively by sycophants and family members. The president has made clear that he cares about loyalty more than qualifications, but the astonishing incompetence and corruption of many of his appointees raises an obvious question: What does it take to get fired by Trump’s White House?
Kimberly Guilfoyle’s resignation yesterday as ambassador to Greece provides some clues. Guilfoyle has been accused of blatant corruption both before and during her time as an envoy. She denies these allegations, but her resignation—which the White House requested—isn’t really about corruption. The idea that Guilfoyle, and only Guilfoyle, crossed some sort of previously unseen corruption red line is laughable. If ethical and legal questions, including the now-moribund standard of “appearances of impropriety,” were grounds for dismissal in this administration, Trump would have already shed several other members of his team.
Rather, Guilfoyle was pushed out because she was an embarrassment. She overstepped her bounds, tried to trade on the president’s name, and then made the administration look bad when she got caught. Also, she is a woman, and in this administration, self-dealing is mostly a man’s game.
Indeed, by comparison with the charges leveled at others—including against the president himself, who seems utterly unconcerned with notions such as “emoluments”—Guilfoyle is decidedly a small-timer. This past spring, for example, the Financial Times reported that a broker for Pete Hegseth attempted to make a big investment in defense industries just before the Iran war, raising suspicions of insider trading. FBI Director Kash Patel has been accused of using government money as a slush fund to pay improper bonuses to his favorites within the Bureau. “Border Czar” Tom Homan was caught on audio in 2024 accepting $50,000 in cash (wrapped in a Cava food bag, always the sign of a deal on the up-and-up) from undercover FBI agents posing as business executives, and yet he remains in his job. Hegseth and Homan deny any wrongdoing; Patel and the FBI have offered no comment or explanation. And the journalist Dexter Filkins recently described Trump’s son-in-law and roving minister-without-portfolio Jared Kushner as representative of “a new kind of Washington figure, for whom public office serves as a means to extraordinary wealth.”
[Read: Trump’s team of mercenaries]
Guilfoyle may have been a relative piker among giants in the grift game, but her real sin was the pathetic and humiliating nature of her behavior. (Even Homan managed not to seem quite so grubby when reportedly accepting a bag of greenbacks.) Her messages to a Trump donor asking for money to help pay her huge credit-card bills are cringe-inducing. “Honey please I need you to get this done for me today,” she wrote to the Trump supporter Eric Deters when asking him to wire a cool $100,000 directly into her American Express account in July 2025, just before her confirmation hearings.
Worse, she continually told Deters to stop writing things down and just contact her on Signal. “What a nightmare you’ll literally cost me my ambassadorship stop writing,” she said. This was apparently Guilfoyle’s version of the infamous “Stringer Bell rule,” named for a character from the television series The Wire who dressed down one of his drug-dealing accomplices for being stupid enough to keep written notes on a criminal conspiracy. The problem is that she, too, violated that rule: She made her requests to Deters to stop writing things down in writing.
Deters, unsurprisingly, kept all the messages. Guilfoyle, he asserts, offered him access to the Trump administration. “I will be your Trump ride or die, forever and ever,” he claims she told him. When she didn’t deliver, he warned Guilfoyle and White House officials earlier this month that he would go public with their correspondence and then made good on that threat.
The newly minted ambassador, meanwhile, was flitting about southeastern Europe in the company of Greek tycoons. But again, rather than enjoy the perks of her job in discreet luxury, she bragged about her connections to these wealthy men and tried to present herself as some sort of made woman from the inner Trump orbit who had the juice to get things done.
According to The Wall Street Journal, she went to Davos in January 2026 and was excluded from a dinner being held for Eric Trump. She decided to pressure an American businessman to help her get in. “You know, I can deliver the world to you. Which you deserve,” she said. (This time, she was caught on audio, rather than by text message.) “I’m going to make you a lot of fucking money,” she told the American. She also raged about the impudence of the dinner’s Greek hostess. “You don’t have the fucking U.S., you know, ambassador to Greece not come. She should be kissing my fucking ass.”
Again, Trump Sr. has no problem with F-bombs; he deploys them regularly. He has no problem with money grabs while in public office; he has enriched himself while president and has explicitly or implicitly blessed similar efforts by other subordinates to profit from their positions. But he apparently draws a line when his son’s former fiancée does not show proper appreciation for the courtesy of being stashed in Athens—Athens!—and then lands in the newspapers looking like an aging waitress cadging tips from marks in a casino. Honey, just put it on the tray. Don’t tell my manager, and I’ll get you to the good poker table.
[David Frum: Trump’s last loyal constituency]
Guilfoyle was once so tight with the Trumps that she was given a prime-time slot to fawn over the president during the 2020 GOP convention. It was a disastrous, over-the-top performance, but Trump loved it, reportedly calling her “my Kimberly” and comparing her to the former Argentine first lady Eva Perón. Earlier this year, Trump said of his emissary to Greece: “Kimberly Guilfoyle has been my friend for a long time. I love calling her Kimber-lay. That’s my little pet name, right? But you are the greatest, and I heard they love you over there.”
But over the past several days, the president saw bad publicity about this demanding, middle-aged woman, thrown over by his son for a younger wife—as Trump himself has done to previous spouses—trying to profit off his presidency while making a fool of herself and encouraging more bad press about corruption just before the midterm elections. Guilfoyle had to go, and Trump jettisoned her quickly and coldly. “She wasn’t a member of my family,” the president said yesterday. “She, uh, I guess dated my son a long time ago.”
“Dated”? I guess? She was in line for years to become the president’s daughter-in-law, married to his first-born son. Now she’s just some dame one of his kids used to know.
Guilfoyle didn’t get it. All she had to do was stay out of trouble. But that was too hard for her, and now she’s learned that making money off this presidency means following some rules. Don’t be too obvious; don’t embarrass the boss; don’t get caught if you can help it. And especially, don’t be an older woman.