Trump Considers Dismissing U.S. Ambassador to Greece Amidst Allegations

President Donald Trump has expressed dissatisfaction with U.S. Ambassador to Greece Kimberly Guilfoyle and is contemplating her removal following reports of questionable conduct. Trump’s comments, indicating “we’re not happy,” coincide with increasing odds on prediction market site Kalshi that Guilfoyle could be dismissed by the year’s end.

The speculation gained momentum after Senate Majority Whip John Barrasso voiced concerns and anticipated an investigation into the situation. An Associated Press report revealed discontent from Trump and Secretary of State Marco Rubio, suggesting a decision about Guilfoyle’s future could be imminent. A senior U.S. official cited claims that Guilfoyle requested a $100,000 wire from a Republican donor for her credit card expenses prior to her Senate confirmation.

Allegations have emerged about Guilfoyle’s alleged luxury travel and connections with Greek business figures. Newsweek reached out to the White House and Guilfoyle’s legal representative Jesse Binnall for comments.

Prediction Markets Show

Kalshi’s data showed the likelihood of Guilfoyle being removed by November 1, 2026, climbed from 43.6 percent on Sunday to 73.9 percent by Monday evening. By December 1, 2026, those odds increased from 79.9 percent to 85 percent in the same timeframe. A similar trend appeared for forecasts predicting her departure before January 1, 2027, rising from 70.6 percent to 86.4 percent between Sunday and Monday.
Polymarket indicates a 73 percent chance of Guilfoyle leaving by October 31 and 78 percent by December 31.

Guilfoyle’s Lawyers Respond

Scrutiny over Guilfoyle intensified following The Wall Street Journal’s report detailing texts allegedly revealing her request for $100,000 from Eric Deters, a prominent Trump donor, in exchange for access to high-ranking officials. AP reports reveal Guilfoyle’s attorneys, David Schwartz and Jesse Binnall, refuting wrongdoing claims and insisting the funds were meant for services rendered through speaking engagements before her nomination.

Regarding private jet travel allegations, Guilfoyle’s legal team maintains that she complied with State Department guidelines and adhered to their travel regulations prior to the trips.

Political analyst Craig Agranoff conveyed to Newsweek that Trump’s expression of dissatisfaction reflects a logical stance, as ambassadors are political appointees and any misconduct involving gifts, travel, or access is initially treated as a personnel issue. He noted that ties to the president and a prestigious position complicate the matter.

Agranoff mentioned loyalty does not eliminate the concern of office misuse. If the investigations absolve Guilfoyle, the story loses traction, but continuing public frustration from Rubio prolongs the issue. Historically, presidents have dismissed ambassadors for less, indicating perceived vulnerability for the administration.

The State Department Office of the Inspector General is reportedly investigating Guilfoyle’s potential acceptance of favors or gifts from private businessmen. In Athens, Rubio remarked, “This is not the forum where we’re going to address it,” maintaining support for the ambassador’s performance.

Vice President JD Vance recently stressed evaluating the allegations factually, asserting consequences should follow if misconduct is proven.