President Donald Trump greets Ambassador to Greece Kimberly Ann Guilfoyle at a celebration in honor of Greek Independence Day at the White House in Washington, D.C., March 26, 2026. REUTERS/Evelyn Hockstein
A now-former ambassador departed the Trump administration amid a mounting scandal, but according to President Donald Trump's one-time biographer, there was a much more personal and "fatal" issue that really led to her ouster.
Last week, reports emerged that Kimberly Guilfoyle, Trump's ambassador to Greece and ex-fiancée of Donald Trump Jr., had pressed a GOP donor to help pay off her $100,000 credit card bill. On Tuesday, after days of increasing heat, she resigned from the office after the new White House Press Secretary, Katie Zacharia, said during his first briefing that she had been asked to leave the administration.
Michael Wolff, meanwhile, claimed there was a deeper reason behind her ouster. Wolff is a longtime reporter and author known for his coverage of Trump's political career, including several books about his first term. In the latest episode of his Daily Beast podcast, "Inside Trump's Head," he told co-host Joanna Coles that while Trump was "not happy" about Guilfoyle's scandals, other major factors were at play in the call to push for her resignation, namely, Trump's family.
"Kimberly Guilfoyle is a reflection of so much that goes on in Trumpworld... Donald Trump sets the model for this," Wolff explained. "It’s ‘gimme gimme gimme,’ across the board. ‘We’re using this position where we can’t believe we’ve gotten into this position where we can effectively extort money from everybody. You have to give me money.' So the question: Why are we hanging Kimberly? One of the answers there is that she’s low-hanging fruit. And the other answer is that they can’t stand her. I mean, the Trumps can’t stand her."
He added: “I think they’ve been asking this question for a long time: ‘How do we get rid of her? How did Don Jr. ever end up with her?’... Everyone is holding their nose. I feel a little bad for her, actually. I mean, this has been a desperate—her climb—a desperate, indefatigable, just clawing up... I mean, just think of how preposterous it is that she became an ambassador.”
Wolff mused about what might be next for Guilfoyle, perhaps another position in or around the Trump administration. Coles suggested that she could end up on a track similar to Kristi Noem, who was ousted as Homeland Security secretary in the spring and moved to a new role as a special envoy for Trump "Shield of the Americas" initiative.
“And Kimberly looks like Kristi Noem, so that might trigger Trump,” Coles said. “He might think, ‘Oh, we have to do what we did for Kristi for her.’”