Kimberly Guilfoyle’s breakup from Donald Trump Jr., announced after the 2024 presidential election, may not have been her idea. But his father, incoming President Donald Trump, reportedly wanted to reward her for her hard work on his campaign and offered her a consolation prize: He nominated her to be his U.S. ambassador to Greece.

Guilfoyle, however, faced an immediate problem ahead of her July 2025 Senate confirmation hearing, according to a bombshell new report in the Wall Street Journal. She complained to friends that she was broke following the end of her engagement to Trump Jr. and she needed to pay down a $100,000 debt to American Express.

So, the former San Francisco prosecutor and Fox News pundit reached out to a Trump donor and asked him to pay the bill — and in a way that wouldn’t leave a paper trail, the Journal reported. In a Signal text to the donor, Eric Deters, she wrote, “It won’t show up anywhere if you wire money to American Express,” she wrote, along with a link to PDF instructions on how to wire the money.

“Honey please I need you to get this done for me today,” Guilfoyle also texted to Deters, adding a prayer hands emoji, according to the Journal, which reviewed the Signal messages.

The texts were sent on July 3, 2025, six days ahead of Guilfoyle’s confirmation hearing. This exchange also occurred as Deters, a former congressional candidate from Kentucky, was seeking Guilfoyle’s help in “getting the attention of the new Trump administration on some personal tax and legal issues,” according to the Journal.

Deters ultimately did not make the payment, telling Guilfoyle that doing so could cost him his marriage, the Journal reported. However, the outlet also said that Deters had promised her payments of as much as $1 million if she was successful. He also complained in a message, sent in June 2025, that he had already her paid her $300,000 over the years and “not received one favor.”

“I am not naive or a sucker. I need results,” he said according to the Journal. In response, Guilfoyle warned Deters about creating a paper trail. She said, “Stop papering all these things. It’s really dangerous.”

“Just call me on Signal,” she wrote, according to the Journal.

Guilfoyle’s lawyer, Jesse Binnall, told the Journal that she disputes the Signal messages’ authenticity, but declined to provide specifics. If Deters made payments to Guilfoyle, Binnall said, it was for his client to speak at events before her nomination. Binnall said she “was owed a balance for traveling to and supporting these patriotic events.” Deters denies he owed Guilfoyle anything.

A U.S. Embassy official told the Journal: “Guilfoyle’s career in and out of public service is guided by deep and abiding values. She was fully vetted by the bipartisan Senate Foreign Relations committee and confirmed by the U.S. Senate. The Ambassador remains committed to representing the American people with dedication and integrity.”

Trump selected Guilfoyle to be ambassador to Greece in December 2024, days after her ex-fiancé was photographed with his new girlfriend and future wife, Palm Beach socialite Bettina Anderson. A year later, in December 2025, Forbes reported that Trump Jr.’s net worth had risen from $50 million to $300 million, largely due to his investments in cryptocurrency.

Guilfoyle’s relationship to Trump Jr. began during his father’s first term, and they became engaged in early 2021. The ex-wife of California Gov. Gavin Newsom, Guilfoyle became one of Trump’s most outspoken supporters and a popular figure at MAGA fundraisers. She also became accustomed to the status that comes with such proximity to the president and to wielding it “like a weapon,” according to a report in the Daily Mail.

Following Trump’s 2020 defeat, she sought to capitalize on being a MAGA icon by launching various business ventures, ranging from public relations and political consulting to lines of hair care and fragrance products, the Journal reported.

Guilfoyle also opened a medspa and started an upscale vodka and champagne brand, American Dream. But she reportedly annoyed Trump by hosting events at Mar-a-Lago to pitch the club’s members on investing in her company. Trump complained that she was supposed to be raising money for him but was instead using his club to raise money for herself, according to the Journal.

Following her breakup from Trump Jr., Guilfoyle filed financial disclosure forms as part of the Senate confirmation process, the Journal reported. Her reported assets included the medspa and the new vodka company, each worth between $1 million and $5 million. She also had earned nearly $800,000 from a podcast.

Her reported liabilities included a boat loan valued at between $100,000 and $250,000 and a mortgage valued at between $1 million and $5 million, the Journal reported. Several months after she and Trump Jr. became engaged, they purchased a mansion together in Jupiter, Florida for $9.7 million. After their breakup, she reportedly tried to sell it for $30 million but didn’t get any offers, and Trump Jr. bought her out of the house for $7.6 million in August, according to Realtor.com.

The Wall Street Journal’s report comes as Guilfoyle is under fire from Democrats on the Senate and House foreign affairs committees, who urged the State Department to review her conduct as ambassador. They cited a previous Journal investigation into allegations that Guilfoyle used her role as a government official to advance private commercial interests, including for a Greek company whose lobbyist traveled with her to meetings with governments across the Balkans.

“If these reports are accurate, Ambassador Guilfoyle is unfit to represent the United States abroad and should be removed from her position,” Representative Gregory Meeks of New York, the top House Foreign Affairs Democrat, said in a letter to Secretary of State Marco Rubio.

Last week, the Daily Mail also reported on Guilfoyle’s demands for a “glitzy Mediterranean lifestyle” while serving as ambassador. As Guilfoyle has been spotted at Paris Fashion Week events or at a “jet-set hangout” on the island of Mykonos, she employs a personal stylist, a “hospitality guru” and a team who manage her social life.

“She has a close team of people that are basically running the show, smoothing the way for her, and making sure she has everything she needs,” a State Department source told the Daily Mail.

Among other things, the team is expected to make sure that a specific, highly priced brand of Champagne is served when she is invited places, the Daily Mail reported. But Guilfoyle doesn’t always get her way: She was reportedly denied a complimentary meal at a Four Seasons hotel restaurant in Athens, according to the Daily Mail. The bill was eventually sent to the embassy, sources familiar with the exchange told the outlet.

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