Trump’s personal-friend diplomats are falling: two out in three days, a third under scrutiny

By Staff Reporter

WASHINGTON — In three days this week, two of President Trump’s most personally connected diplomatic appointees lost their jobs. A third, a senior aide at one of Washington’s most sensitive embassies, is under scrutiny over a New York Times investigation.

On Tuesday Kimberly Guilfoyle was pushed out as ambassador to Greece. Paolo Zampolli was removed on Thursday as special envoy for global partnerships. Their ties to the Trump family were unusually personal: Guilfoyle was engaged to the president’s eldest son, and Zampolli has said he introduced Melania Trump to her future husband. Both departures followed damaging press reports. Together they mark a change in an administration that has given wide latitude to political appointees in diplomatic posts, and they suggest that the State Department’s leadership, Secretary Marco Rubio and Deputy Secretary Christopher Landau, now has less patience for them.

Guilfoyle: “I didn’t like what I read”

Katie Zacharia, the new White House press secretary, said at her first briefing Tuesday that the White House had “asked Ambassador Guilfoyle to resign,” CNN reported. Guilfoyle’s formal resignation arrived later that day (AP; Washington Post). “I didn’t like what I read,” Trump said. He added that Guilfoyle “wasn’t a member of my family” and had “dated my son a long time ago.”

What he read included a Wall Street Journal report and others alleging that before her Senate confirmation, Guilfoyle sought money in exchange for access to administration figures. The reports also alleged that she accepted lavish gifts as ambassador and brought a lobbyist for a Greek construction company into official meetings. Eric Deters, a former Trump donor, said she texted him asking him to wire $100,000 to pay an American Express bill. He said he did not send it and told CNN, “No question it was a quid pro quo.”

Guilfoyle denies all of it. Her lawyers said Deters owed her money for speeches and consulting work. “Asking a client to pay for work already done is not corruption,” they wrote. They called reports about her travel misleading and said she complied with federal gift and reporting rules. On X, she said the allegations were “false” and that she intends to “vigorously defend my name.”

The State Department’s inspector general is investigating, according to a source familiar with the effort cited by CNN. The inspector general’s office said it does not confirm or deny investigations. Democrats on the House Foreign Affairs Committee have said her resignation “does not shield her from accountability.”

Zampolli: an email war goes public

Two days later it was Zampolli’s turn. On Thursday, Politico published a long account of a monthslong email feud between Zampolli and Landau. It covered how far Zampolli’s authority extended beyond cultural diplomacy, and the messages included personal attacks. Within hours, a U.S. official told CNN that Zampolli “was notified today that his status as an envoy has been terminated and he is no longer a government employee” (Politico).

Zampolli is a former modeling agent who represented Melania Trump and says he introduced her to Trump at a 1998 party. Trump named him special envoy in March 2025. Zampolli took the news warmly. “The President is always right,” he said in a statement, adding that Trump had told him, “Why do you want to work in government when you can close all these deals?”

The Huckabee aide

The third case has not ended in a departure. On Oct. 8 The New York Times reported that David Milstein, a senior adviser to Ambassador Mike Huckabee in Jerusalem, had for more than a year sought to water down, delay or block embassy reporting on Israeli government actions, especially settler violence in the West Bank. The Times based the report on interviews with 15 U.S. officials and dozens of internal cables and memos (Times of Israel summary).

Huckabee rejected the report. “I personally and categorically refute the elements of your proposed ‘story,'” he told the Times. The State Department said only that “the entire team at State remains focused on advancing President Trump’s America First agenda.” Milstein is the stepson of Fox News host Mark Levin. In September Politico reported that he had asked Israeli guests for monetary wedding gifts. He appeared to withdraw the request, writing to guests that “we cannot accept gifts of any kind.”

A pattern, and its limits

Every administration has political ambassadors. What these cases have in common is that the appointees’ main qualification was personal closeness to the president or his family, and that internal resistance came into public view. In Guilfoyle’s case, CNN, citing people familiar with the matter, reported that Rubio “in particular was eager to see her gone.” In Zampolli’s, his adversary in the email war was Landau, the department’s No. 2.

There are limits to calling it a purge. Trump explained Guilfoyle’s removal in his own words. Zampolli’s envoy post had been a one-year appointment that Trump had already extended by six months. And no departure has been announced for Milstein.

The next steps are in other hands. Any successor in Athens will need Senate confirmation. Rep. Gregory Meeks, the top Democrat on House Foreign Affairs, has said Congress must determine “whether Ambassador Guilfoyle solicited funds from any other source.” The inspector general’s work may continue after her departure, depending on whether the Justice Department opens its own inquiry, CNN reported.

Photo: The State Department’s Harry S Truman Building. Official State Department photo by Linda D. Epstein, public domain, via Wikimedia Commons.