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Kimberly Guilfoyle’s Secret Cash Plea for Luxury Car Exposed

The fired ambassador reportedly made another giant ask before her confirmation hearing.

PARIS, FRANCE - JANUARY 28: (EDITORIAL USE ONLY - For Non-Editorial use please seek approval from Fashion House) Kimberly Guilfoyle attends the Elie Saab Haute Couture Week Spring/Summer 2026 show as part of Paris Fashion Week on January 28, 2026 in Paris, France. (Photo by Aurore Marechal/Getty Images)

Aurore Marechal/Getty Images

New details about former Ambassador to Greece Kimberly Guilfoyle’s high-maintenance demands have been revealed.

Guilfoyle resigned Tuesday at President Donald Trump’s request, after he told the world he was “not happy” with her amid a flurry of scandals, including her alleged financial dealings with a MAGA donor, her lavish Mediterranean lifestyle, and her abusive behavior toward staff.

The State Department launched an investigation into Guilfoyle last week.

The State Department launched an investigation into Guilfoyle last week.

Louisa Gouliamaki/REUTERS

Now, the Daily Mail reports that while Guilfoyle was reportedly pressuring a right-wing donor to pay her $100,000 American Express bill before her Senate confirmation hearing last summer, she was also allegedly trying to get wealthy Greek businessmen to pay $250,000 in loans on her Mercedes G-Wagon.

Guilfoyle, 57, approached the businessmen with the request, according to four Greek and State Department insiders. But as with her AmEx bill, she did not get the money she wanted, according to the report.

The State Department did not immediately respond to a request for comment from the Daily Beast.

Last week, the State Department’s inspector general launched an investigation into Guilfoyle into what the Mail called “potential substance abuse, use of private planes and helicopters, close relationship with an energy and construction company, improper gift acceptance, and more.”

Guilfoyle was reported to have demanded comped meals and top-end champagne, all the while allegedly being “tyrannical” toward embassy staff.

Kimberly Guilfoyle, the National Chair of the "Trump Victory Finance Committee" and girlfriend of Donald Trump Jr., delivers a pre-recorded speech to the largely virtual 2020 Republican National Convention from Washington, U.S., August 24, 2020.

Guilfoyle's behavior has spurred a State Department investigation.

KEVIN LAMARQUE/REUTERS

Trump admitted his displeasure with Guilfoyle in public on Monday, telling reporters, “We’re not happy.”

The following day, new White House Press Secretary Katie Zacharia announced that Guilfoyle had been asked to resign.

After Guilfoyle did so, Trump downplayed her connection to him.

“No, she wasn’t a member of my family. She, I guess, dated my son a long time ago,” he said.

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Guilfoyle was engaged to Donald Trump Jr., 48, from late 2020 to 2024, and one of their final public appearances was at that year’s Republican National Convention. Trump Jr. was seen with socialite Bettina Anderson a few months later. They got married in May.

In a statement announcing her resignation prior to the Mail’s report, Guilfoyle addressed “the recent allegations” against her.

“These allegations are false, and I intend to vigorously defend my name, my reputation, and my integrity,” she wrote. “I have dedicated my professional life to fighting for justice, standing up for what is right, and defending the values that make America exceptional. I will not allow false accusations to define my decades of public service.”

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