In late 2024, as Donald Trump was preparing to take office for a second time, he had to navigate a ticklish family situation. Until recently, his son Donald Trump, Jr., had been engaged to Kimberly Guilfoyle, a former Fox News host who was once married to California Governor Gavin Newsom, and Guilfoyle had become a leading figure in Trump’s orbit. She spoke—or, more precisely, shouted—on his behalf at the 2020 Republican National Convention (“They want to enslave you to the weak, dependent, liberal, victim ideology, to the point that you will not recognize this country or yourself,” Guilfoyle said of Democrats) and served as the national finance chair for Trump’s campaign. Speaking at the “Save America” rally that preceded the assault on the Capitol on January 6, 2021, Guilfoyle vowed, “We will not allow the liberals and the Democrats to steal our dream or steal our election.” The conservative group Turning Point Action paid her sixty thousand dollars for the three-minute appearance. Guilfoyle was, in short, as Eric Trump said in introducing her that day, “a warrior” for Trump.
Four years later, Guilfoyle had become less helper than headache. Trump, Jr., had been seen with another woman, a Palm Beach socialite to whom he is now married, and the couple’s engagement was called off. “I had to get her out of here,” Trump reportedly told people. (The White House has denied that Trump made this statement.) The solution: naming Guilfoyle Ambassador to Greece, a country with which she had no clear ties—her mother is from Puerto Rico, her father from Ireland—but that became, or so it appeared, a convenient place to stash the inconvenient ex.
Those who had paid attention to Guilfoyle’s past might have questioned her diplomatic skills. She was forced to leave Fox in 2018 over allegations of questionable workplace behavior. Two years later, my colleague Jane Mayer reported on the details: one of Guilfoyle’s assistants had accused her of repeated sexual harassment. The assistant, Mayer wrote, claimed to have been subject to “degrading, abusive, and sexually inappropriate behavior; among other things, she said that she was frequently required to work at Guilfoyle’s New York apartment while the Fox host displayed herself naked, and was shown photographs of the genitalia of men with whom Guilfoyle had had sexual relations.” (Guilfoyle denied wrongdoing.) Fox paid “upward of four million dollars” to settle the complaint.
On Tuesday, Guilfoyle was forced to resign from the ambassadorship a year into the post, for problems of a different nature: financial, not sexual, although her provocative attire as Ambassador also drew attention. (Among other fashion choices, Guilfoyle, who travels with a stylist, wore a see-through black lace dress to a Thanksgiving dinner hosted by the American-Hellenic Chamber of Commerce.) The Wall Street Journal had published a devastating trio of stories about Guilfoyle’s behavior on the job. First came a piece in late September about Guilfoyle’s unusually dogged advocacy on behalf of a Greek construction firm, the Aktor Group, which was seeking to break into the energy business; Christos Marafatsos, a top lobbyist for the company, “has attended so many of her meetings that some foreign officials mistook him for her chief of staff,” the Journal wrote. (Aktor and attorneys for Guilfoyle have denied any improprieties.) Then, last week, the Journal reported on Guilfoyle’s beseeching a Trump donor to wire her a hundred thousand dollars to pay her American Express bill in advance of her confirmation hearing. “Honey please I need you to get this done for me today,” Guilfoyle texted the donor, Eric Deters, adding a prayer-hands emoji. Deters, a Kentucky lawyer and former congressional candidate, had already paid Guilfoyle three hundred thousand dollars; among other things he sought a meeting with the commissioner of the Internal Revenue Service to discuss his tax problems. “As of this memo, I have not received one favor,” Deters wrote. “I am not naive or a sucker. I need results.”
Guilfoyle, a lawyer and former prosecutor—she overlapped with Kamala Harris in the San Francisco district attorney’s office—understood the risk posed by Deters’s digital trail. “Stop papering all these things,” she warned, advising Deters to call her on Signal instead. “It’s really dangerous.” Deters ultimately balked at the AmEx payment. “I can’t do this without getting a divorce,” he told Guilfoyle. (Guilfoyle has suggested the texts were generated by A.I. and said, “I will not allow false accusations to define my decades of public service.”)
The Journal’s final blow, on Saturday, described how Guilfoyle accepted luxury travel, including from a Greek shipping magnate who hosted Guilfoyle on his private jet and paid her bill at the Four Seasons Hotel George V, in Paris, while she was in town to attend his wife’s fashion show. Lobbying an unnamed U.S. businessman to secure an invitation to a dinner at the World Economic Forum in Davos in honor of Eric Trump, Guilfoyle promised, “I’m going to make you a lot of fucking money,” according to a recording reviewed by the Journal.
In March, celebrating Greek Independence Day at the White House, Trump described Guilfoyle as “a person I know very, very well” and “an inspiration to a lot of people.” On Tuesday, that relationship was significantly downgraded. “She wasn’t a member of my family,” Trump told reporters. “She, I guess, dated my son a long time ago.” Kimberly who? That new chilliness was no surprise. Guilfoyle was guilty of what is, to Trump, a capital offense: her reported grift may have been comparatively small, but it failed to benefit the President and, indeed, made him look bad. Guilfoyle joined a very short list of Trump Administration officials whose ethical offenses were deemed serious enough to warrant expulsion. The other leading example from Trump’s second Administration is the former Secretary of Homeland Security, Kristi Noem, who erred, among other things, by spending two hundred and twenty million dollars in a taxpayer-funded campaign featuring the Secretary, on horseback, in front of Mt. Rushmore. Noem’s mistake was not so much promoting herself as failing to promote her boss—and, for good measure, asserting that he had been aware of her spending.
The paradox of Trump Administration corruption is that the most egregious offenders—the President chief among them—operate in plain sight and on a grand scale. They don’t fret, to borrow Guilfoyle’s verb, about “papering” the evidence; they consider themselves, perhaps with good reason, immune from consequences. To borrow from Nixon’s answer to David Frost, when the President does it, that means it is not grifting. Trump imposed some constraints on his own and his immediate family’s dealings during his first term—he promised, for example, that the Trump Organization would not conduct business abroad—but these limits, such as they were, have been shrugged off in the second. As Trump explained to the Times in January, “I found out that nobody cared. . . . I got absolutely no credit for it.”
My colleague David Kirkpatrick calculated that during the first year of his second term, Trump and his family leveraged the Presidency to make more than four billion dollars, dealing in cryptocurrency, foreign real-estate investments, and prediction markets. That total does not include the potential value of Trump’s collusive “settlement” of a private lawsuit against the I.R.S. for the leak of his tax information; as part of the arrangement, the government agreed that Trump, his family, and his companies would be immune from back taxes and penalties. Meanwhile, the President’s son-in-law Jared Kushner is both an unpaid negotiator for the Trump Administration and the owner of an investment firm, Affinity Partners, that is almost entirely financed by Saudi Arabia and other Middle Eastern countries.
When there are consequences for Trump family members’ overreach, they tend toward the minimum. Last month, ProPublica reported that a Russian oligarch close to Vladimir Putin had paid hundreds of thousands in expenses for Donald Trump, Jr., and his new wife, Bettina Anderson Trump’s May wedding celebration, including renting out a private island and putting on a fireworks display. The President described this arrangement as “very common” and “totally allowed,” but said his son was repaying the oligarch. Contrast that seeming nonchalance with Trump’s response to reports of profiteering by James Blair and Chris LaCivita, two of his senior political advisers. On October 6th, the Times reported that, in the heat of the U.S. midterm campaign, the pair had travelled to Republika Srpska, a self-governing territory in the Balkans, to help the pro-Russia government in advance of its own elections. Blair, the former deputy White House chief of staff, and LaCivita, a co-manager of Trump’s 2024 campaign, were paid hundreds of thousands of dollars through a Washington law firm, the Times said. Trump, typically, diminished his relationship with the two men, calling them “outside consultants” who “do not work for me.” He added, “I do not have any idea who else they work for but will, on reflection, ask them and, if there’s a conflict, I will terminate them, immediately!”
Guilfoyle would seem to require particularly careful handling. Having dated Don, Jr., for years, she presumably knows a lot of Trump family and Trump business secrets. So it was something of a surprise that the White House opted not to accord her the ordinary face-saving courtesy of announcing her own departure. Instead, the new White House press secretary, Katie Zacharia, said Guilfoyle had been asked to resign. Zacharia added, incongruously, “She has been a wonderful asset to the team.” What, one wonders, would count as a liability? ♦