Trump Considers Dismissing U.S. Ambassador to Greece Amid Conduct Allegations

President Donald Trump informed reporters on Monday about the possibility of removing U.S. Ambassador to Greece Kimberly Guilfoyle after reports emerged about her conduct. Trump mentioned, “we’re not happy.” These remarks coincided with rising predictions on market site Kalshi that she might be ousted by the year’s end.

Senate Majority Whip John Barrasso expressed concern and anticipated an investigation into the reports. The Associated Press indicated that both Trump and Secretary of State Marco Rubio were reportedly “extremely pissed off” about Guilfoyle’s alleged actions and could decide her fate soon. According to a senior U.S. official, Guilfoyle reportedly asked a Republican donor for $100,000 to settle her credit card bill prior to her Senate confirmation hearing, with additional reports citing luxury travel and relationships with Greek business figures.

Newsweek reached out to the White House and Guilfoyle’s attorney, Jesse Binnall, for further comments on Monday night.

Prediction Markets Analysis

Kalshi displayed a jump in predictions on Guilfoyle’s potential departure. Odds for her exit before November 1, 2026, were 43.6% on Sunday evening, rising to 73.9% by Monday night. Projections for her departure before December 1, 2026, increased from 79.9% to 85% during the same period. Predictions for her leaving before January 1, 2027, rose from 70.6% to 86.4% by Monday night. Polymarket suggested a 73% probability of her exit by October 31 and 78% by December 31.

Response from Guilfoyle’s Legal Team

Allegations against Guilfoyle, formerly engaged to Donald Trump Jr., resurfaced following a Wall Street Journal report. Text messages purportedly showed her requesting longtime Trump donor Eric Deters to pay $100,000 for her American Express bill in return for senior administration access. Lawyers David Schwartz and Jesse Binnall defended Guilfoyle, claiming the funds were for pre-nomination speaking engagements and public appearances.

“Ambassador Guilfoyle has served, and will continue to serve, with integrity, honor and distinction. We are evaluating all available legal remedies to collect this debt and any other potential causes of action,” stated the lawyers according to the AP.

The lawyers also addressed private flight allegations, stating that Guilfoyle complied with State Department guidelines and travel regulations.

Political Reactions and Investigations

Political analyst Craig Agranoff observed, “Trump saying he is looking into it and is not happy is the practical response. Ambassadors are political appointees, and when reports question gifts, travel, or access, the White House treats them as personnel issues first.” Agranoff highlighted, “Loyalty does not erase the appearance of using the office. If the allegations are proven, it becomes a significant issue.” Rubio, publicly frustrated, mentioned the ongoing investigation by the State Department Office of the Inspector General.

Vice President JD Vance, upon addressing the allegations, remarked, “These are allegations…let’s actually see what the facts are, let’s see what the truth is. And obviously if there was something bad that happened, then people have to suffer consequences for it.”