President Donald Trump has spent years publicly gushing over Kimberly Guilfoyle.
Earlier this week, he could barely spare her a full sentence when asked about plans to fire his son Donald Trump Jr.’s ex-fiancée from her cushy post as America’s ambassador to Greece.
The president didn’t rush to her defense or sing her praises. Instead, he treated her like a woman he never met and barely said anything at all.
“Well, we’re looking at it,” Trump told reporters Monday, adding, “we’re not happy.”
According to CNN, the State Department’s Office of Inspector General is investigating Guilfoyle. When a reporter asked Trump about the allegations Friday, he offered no defense.
On Tuesday, Oct. 13, the new White House press secretary, Katie Zacharia, took to the podium in the James S. Brady Press Briefing Room to deliver her first briefing as Karoline Leavitt used to.
Zacharia took questions from the press before being asked about Trump firing Guilfoyle.
“We have asked Ambassador Guilfoyle to resign. She has been a wonderful asset to the team, and we wish her well,” she stated before moving on.
After the briefing, the press waiting outside the White House asked Trump about Guilfoyle. He made sure to state that they were never family.
“She was not a member of my family. I guess [she] dated my son a long time ago. But she wasn’t [family,” Trump said, adding that “she was doing a good job. But we didn’t like what we read. I didn’t like what I read.”
The trouble stems from a bombshell Wall Street Journal investigation into Guilfoyle’s dealings with Eric Deters, a Kentucky attorney and longtime Trump donor. Deters sought her help to bring his personal tax and legal issues to the Trump administration.
According to the Journal, Guilfoyle pressed Deters in July 2025 to pay a $100,000 American Express bill just days before her Senate confirmation hearing.
“It won’t show up anywhere if you wire money to American Express,” she allegedly wrote in a Signal message, according to Newsweek.
Deters said he saw the request as an attempt to trade money for access through Guilfoyle’s connections, but he never paid because his wife wouldn’t approve.
Guilfoyle has denied wrongdoing and reportedly told administration officials last week that she never sent the messages.
It’s a sharp turn from December 2024. Trump praised Guilfoyle as “a close friend and ally” with “sharp intellect” when he announced her nomination on Truth Social.
The announcement came as Don Jr., her fiancé for four years, went public with his then-girlfriend, Bettina Anderson, whom he married in May. Online critics ran wild with jokes that Trump was shipping his son’s ex overseas.
As Guilfoyle awaits her final day, an old photo of her beside Trump began circulating, sparking a different conversation.
In the image, shared on X, Trump sings into a microphone while Guilfoyle stands beside him with her arms folded tightly across her waist. She wears a plunging black dress with a sheer mesh neckline and a see-through panel running up her thigh.
The photo appears to be from a March 2024 fundraiser Guilfoyle hosted at Mar-a-Lago for Arizona congressional candidate Abraham “Abe” Hamadeh.
But it’s the same dress that reportedly drew backlash. An X user, who noticed the resurfaced image Monday, wondered what occasion Guilfoyle “was dressing for” and about the look on her face.
“She looks like she is deeply regretting her life choices in that photo,” one user wrote. Another zeroed in on her body language, writing, “She looks extremely uncomfortable. Crossed arms over her stomach, very defensive posture.”
Even some of her harshest critics softened, as one admitted: “I despise her, but really feel sorry for her when I look at this photo.”
Others turned the focus back on the president. One user argued, “She was on Ozempic because she had gained weight. But the Trumps never really liked her. Trump didn’t want Don Jr to marry her & the rest of the family could not stand her.”
Another Trump critic pointed out, “To go from Gavin Newsom, then to Junior, and now she’s facing legal issues, WOW. Once you’ve outlived your usefulness with Mar-A-Lago, you’re pretty much done.
Another recalled how Republicans once clutched their pearls over Michelle Obama baring her arms in a sleeveless dress, writing simply, “How times change.”
The resurfaced photo lands less than a week after Guilfoyle made headlines in Athens for a very different reason.
When Secretary of State Marco Rubio touched down in Greece, she greeted him on the tarmac. He threw his arms around her neck, but appeared to lean back to keep his distance.
Rubio stood by Guilfoyle anyway. At a joint news conference with Greece’s foreign minister, Rubio declined to address whether the State Department was investigating her.
His only response was, “Our ambassador has been a strong ambassador here.”
It’s also not the first time a conservative woman’s wardrobe has upstaged her politics.
Back in March, Megyn Kelly tore into Trump over Iran, but it was the thigh-high dress from her Vladimir Putin interview that went viral all over again.
Whether Trump ends up standing behind Guilfoyle the way his secretary of state did remains to be seen. For now, all he’s offering is that he’s “looking at it.”
Remember this picture of Kimberly Guilfoyle, what the hell was she dressing for or who? Do you think she looked good in this pic? https://t.co/ohFX6hVTua
— Suzie rizzio (@Suzierizzo1) October 12, 2026
