President Donald Trump sharply distanced himself from former Greek Ambassador Kimberly Guilfoyle, 57, as her tenure ended amid a storm of negative headlines.
Guilfoyle resigned on Tuesday after weeks of scrutiny, including an exclusive report from Our News Outlet that she was facing an Inspector General investigation into her lifestyle and spending while serving in Athens.
A reporter asked Trump whether he had been surprised by the allegations involving Guilfoyle, who was described as having been “almost a member” of his family.
“No, she wasn’t a member of my family,” Trump replied.
He then minimized their connection, saying, “She, I guess, dated my son a long time ago.”
Guilfoyle began dating Donald Trump Jr. in 2018, several months after his separation from Vanessa Trump. The couple quickly became a prominent pairing within the MAGA movement.
Trump Jr. proposed on New Year’s Eve in 2020, but the couple never made it to the altar. Their six-year relationship eventually ended quietly, and by late 2024 he had begun a new romance with Palm Beach socialite Bettina Anderson.
Our News Outlet recently obtained exclusive text messages offering fresh insight into the private and complicated collapse of Trump Jr. and Guilfoyle’s engagement.
Trump dismissed the suggestion that Guilfoyle was family, saying she had only “dated my son a long time ago.”
Donald Trump Jr., who began seeing Guilfoyle after his 2018 split from Vanessa Trump, was reportedly seen kissing the model during the outing, according to witnesses (Source: Kimberly Guilfoyle/Instagram)
During her first briefing, Trump’s new press secretary, Katie Zacharia, said the president had asked Guilfoyle to leave her post.
“We have asked Ambassador Guilfoyle to resign. She has been a wonderful asset to the team, and we wish her well,” Zacharia said in response to a question from Our News Outlet.
A source close to Guilfoyle said she reacted badly to the decision, reportedly offering explanations and arguing that the move was unfair.
In a statement shared on X, Guilfoyle rejected the allegations as “false” and promised to vigorously defend her reputation as her service as US ambassador to Greece comes to a close.
“I will not allow false accusations to define my decades of public service,” Guilfoyle wrote. “While my time as Ambassador may be coming to an end, my commitment to President Trump, the America First movement, and the country I love will never end.”
She also expressed gratitude to Trump and Secretary of State Marco Rubio, highlighted her work in Athens and pledged to remain a loyal supporter of the president and his MAGA agenda.
Trump had said Monday that he was considering removing the US ambassador to Greece following a series of reports about her conduct.
Bettina and Donald Trump Jr. celebrated with a lavish May wedding party and shared previously unseen photos on Instagram Monday (Source: Bettina Trump/Instagram)
Donald Trump Jr. and Bettina Anderson attended the couple’s lavish bridal shower at Mar-a-Lago in April (Source: yazchernandez/Instagram)
Kimberly Guilfoyle, President Trump’s nominee for US ambassador to Greece, appeared alongside him during a Greek Independence Day celebration in the White House East Room in Washington, DC, on March 24, 2025.
White House Press Secretary Katie Zacharia speaks during a news briefing in the James S. Brady Press Briefing Room of the White House on October 13
Our News Outlet exclusively reported last week that the State Department officially opened a probe into complaints into Guilfoyle’s allegedly ‘tyrannical’ leadership and lavish corporate perks at the US Embassy in Athens.
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Three sources said the IG is looking into allegations surrounding Guilfoyle’s potential substance abuse, use of private planes and helicopters, close relationship with an energy and construction company, improper gift acceptance and more.
The bombshell came in Zacharia’s first briefing after her rapid 72-hour ascent to the top media job in the country as Trump faces an onslaught of brutal headlines ahead of the midterm elections in just three weeks.
Replacing Karoline Leavitt, the 41-year-old lawyer and political commentator is being thrown straight into the lion’s den, getting ready to field a barrage of questions from a press corps eager to probe a series of burgeoning political controversies.
The new press secretary lived in California with her husband and their children before moving to Washington, DC, just days ago after Trump offered her the job.
She cut the briefing short, taking questions only from Our News Outlet, Breitbart and Fox News after 14-minutes at the podium.
But her debut was undoubtedly defined by the stunning announcement on Guilfoyle.
The diplomat had faced mounting pressure over allegations that she solicited a $100,000 donor payment toward personal credit card debt in exchange for political access, and other accusations of unethical behavior the administration is scrambling to address.
Zacharia holds her first press briefing at the White House in Washington
Last week, the top Democrats on the Senate and House foreign affairs committees urged Secretary of State Marco Rubio to investigate Guilfoyle.
‘If these reports are accurate, Ambassador Guilfoyle is unfit to represent the United States abroad and should be removed from her position,’ wrote Representative Gregory Meeks of New York, the top House Foreign Affairs Democrat.
Our News Outlet has exclusively reported that her party girl lifestyle has landed Guilfoyle in hot water with members of Trump’s family.
Trump-world insider Eric Deters, who Guilfoyle reportedly asked for a six-figure payment, told Our News Outlet that she recruited Deters’ wife and her friend to secretly sneak alcohol to her during a political festival, acting ‘like a high schooler’ hiding booze from her parents.
When the event ended, Guilfoyle insisted on packing up all the leftover catered VIP food to take home, Deters said.
He added that she begged him to compliment her in front of Donald Trump Jr, her former fiancé, in the hope of ‘winning back his favor.’
Zacharia touted Trump’s achievements in a long monologue where she focused on energy, telling reporters that the president ‘secured the biggest oil deal in world history’ after his toppling of Venezuelan dictator Nicolas Maduro
She is a California native and Pepperdine Law graduate
Trump had grown enamored with Zacharia’s performances on his favorite channel, Fox News, before making her his new press secretary
Guilfoyle’s affinity for Champagne and parties have widely been documented, and insiders urged her to be on good behavior after she was tapped to be President Donald Trump’s Greek Ambassador, cautioning that an assignment amid Aegean islands and endless summers wasn’t a green light for nonstop partying.
Guilfoyle’s lawyers have hit back at the allegations, insisting the dispute with Deters concerns unpaid work rather than an attempt to sell access to the administration.
In a statement reported Monday, they said he owed her approximately $150,000 for speaking engagements and consulting work performed in 2024 and early 2025.
Still, Republicans have begun to sour on Guilfoyle, with Senate Majority Whip John Barrasso telling CBS anchor Margaret Brennan on Face The Nation Sunday that the reports about the ambassador were ‘very troubling,’ as well as ‘concerning.’
He added that he expected the State Department to conduct an investigation into the ambassador, before noting that ‘the Senate Foreign Relations Committee will have oversight and look into that as well.’
