Kimberly Guilfoyle apparently tried almost everything to save her job as Donald Trump’s ambassador to Greece.
She blamed leakers.
She sought help from political allies.
She reportedly tried to get damaging coverage taken down.
And when confronted with text messages allegedly showing her asking a Trump donor for $100,000, she reportedly offered an extraordinary explanation:
They were created by artificial intelligence.
The defense failed.
Trump ultimately asked Guilfoyle to resign Tuesday after weeks of allegations surrounding her financial dealings and conduct in Athens.
The Wall Street Journal reported Wednesday that Guilfoyle’s final days in office were marked by a frantic effort to convince the administration that the scandals surrounding her should not cost her the ambassadorship.
The most damaging controversy centered on Republican donor Eric Deters.
The Journal previously reported that Guilfoyle asked Deters to send $100,000 directly to her American Express account in July 2025, shortly before her Senate confirmation hearing.
According to messages reviewed by the newspaper, Guilfoyle allegedly told Deters that sending the money directly to American Express would prevent the transaction from appearing elsewhere.
Deters did not make the payment.
He later characterized the request as a quid pro quo, alleging that Guilfoyle had discussed helping him gain access to influential figures inside Trump’s administration.
Guilfoyle has denied wrongdoing, and her lawyers have disputed the authenticity or characterization of the communications.
But as the controversy reached the White House, Guilfoyle reportedly made another argument.
She told administration officials that the incriminating text messages had been generated using AI, according to the Journal.
The White House reportedly did not believe her.
People magazine independently reported the same account, saying Guilfoyle tried unsuccessfully to persuade officials that the messages were artificial.
That was only one part of her reported effort to survive.
As stories about her tenure continued to emerge, Guilfoyle allegedly began blaming U.S. Embassy staff and members of her security team for leaking information about her activities.
The Journal also reported that she reached out to figures in conservative media and Trump’s political orbit in hopes of getting help with the administration.
Among them was Breitbart editor Matthew Boyle, whom Guilfoyle reportedly urged to put in a favorable word for her with Trump officials.
It is unclear whether Boyle ultimately intervened.
Another fight reportedly involved allegations about Guilfoyle’s lifestyle in Greece.
Media reports accused her of seeking complimentary luxury services, including champagne and an expensive dinner at an upscale Athens Riviera restaurant.
According to the Journal, Guilfoyle pressed State Department officials to help get one of the stories removed.
Officials then allegedly asked her to provide documentation showing she had paid for the meal.
She did not provide a receipt, according to the newspaper.
Those allegations were added to a growing list of concerns about her conduct.
Guilfoyle was accused of allowing people with private business interests unusual access to diplomatic events, promoting the interests of a Greek company and accepting benefits from wealthy contacts.
Reuters reported that the allegations included claims that she sought money, gifts or favors while offering access to powerful Trump administration figures.
Guilfoyle denies those allegations.
The controversy became serious enough that the State Department inspector general began examining complaints connected to Guilfoyle’s tenure.
No criminal court has found Guilfoyle guilty of corruption, bribery or any other offense.
The existence of an investigation does not establish wrongdoing.
But politically, the damage was becoming difficult for the White House to ignore.
Trump made that clear Monday.
Asked whether Guilfoyle could lose her job, he told reporters:
“Yeah, we’re not happy.”
The following day, new White House press secretary Katie Zacharia announced that the administration had asked Guilfoyle to step down.
“We have asked Ambassador Guilfoyle to resign,” Zacharia said.
“She has been a wonderful asset to the team, and we wish her well.”
Guilfoyle complied.
In her resignation statement, however, she insisted she had done nothing wrong.
“These allegations are false,” she said, adding that she intended to vigorously defend her name, reputation and integrity.
She also reaffirmed her loyalty to Trump and the America First movement.
Trump sounded considerably cooler when he spoke about her departure.
“She went to Greece, she was doing a good job, but we didn’t like what we were reading,” he told reporters.
“I didn’t like what I read.”
He also pushed back when Guilfoyle was described as having once been part of his family.
“She wasn’t a member of my family,” Trump said.
“She, I guess, dated my son a long time ago.”
The comment was notable because Guilfoyle’s relationship with Donald Trump Jr. was hardly casual.
The pair began dating in 2018 and became engaged before breaking up in 2024.
For years, Guilfoyle was one of the Trump family’s most visible political surrogates.
She raised money, campaigned alongside them and became a fixture at major MAGA events.
Trump later nominated her to the prestigious diplomatic post in Athens.
Less than a year after her confirmation, that chapter is now over.
According to the Journal, Trump was particularly troubled by the perception that Guilfoyle may have been using her proximity to his presidency for personal financial benefit.
Senior aides were also reportedly worried that the scandal reinforced Democratic accusations that the administration tolerated self-dealing.
With the midterm elections only weeks away, the political cost of keeping her became increasingly difficult to justify.
Guilfoyle’s departure also created complications beyond Washington.
Associated Press reported Wednesday that officials in Greece are concerned about losing an ambassador with unusually direct access to Trump at a sensitive moment in U.S.-Greek energy and defense relations.
Guilfoyle had become a high-profile figure in Athens and was heavily involved in efforts to expand American energy influence in southeastern Europe.
But it is the reported chaos of her final days that may ultimately define her exit.
A disputed $100,000 request.
Claims that damaging messages were created by AI.
Allegations of internal leakers.
Attempts to enlist conservative-media allies.
A reported effort to challenge damaging press coverage.
And, finally, a president who decided he had heard enough.
Guilfoyle says the allegations against her are false.
She may yet challenge them publicly or legally.
But her campaign to save her ambassadorship has already reached a definitive conclusion.
The White House did not believe enough of her defenses to keep her in Athens.
And after years of being one of Trumpworld’s most recognizable insiders, Guilfoyle is suddenly on the outside.
