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Kimberly Guilfoyle was preparing for her congressional hearing to become U.S. ambassador to Greece when she reached out to a Trump donor with an urgent request: She needed $100,000 that she said she owed American Express—in a way that wouldn’t leave a paper trail.

“It won’t show up anywhere if you wire money to American Express,” she wrote on Signal, according to messages reviewed by The Wall Street Journal. “Please.”

For months, Guilfoyle had been chatting with Eric Deters, a former congressional candidate in Kentucky who was seeking her help in getting the attention of the new Trump administration on some personal tax and legal issues—and had promised payments of as much as $1 million if she was successful. As Donald Trump Jr.’s former fiancée, Guilfoyle offered to use her sway, according to Deters and messages reviewed by the Journal. She forwarded Deters the messages she’d sent to the new Internal Revenue Service chief and updated him on her efforts to lobby the Justice Department on his behalf.

But her confirmation was coming up, and she needed her card balance paid down before then, she said…..“Honey please I need you to get this done for me today,” she texted Deters, adding a prayer hands emoji and a PDF with bill payment instructions from American Express. “You could just send it here,” she wrote on July 3, 2025, just days before her July 9 confirmation hearing.

Deters didn’t ultimately make the payment, telling Guilfoyle it would cost him his marriage. But the back and forth, part of a tranche of hundreds of messages, emails and letters reviewed by the Journal, raises new questions about the activities of one of America’s most high-profile ambassadors.

Last week, Guilfoyle came under fire from Democrats on the Senate and House foreign affairs committees, who urged the State Department to review her conduct. They cited a Journal investigation into her promotion of a Greek company whose lobbyist traveled with her to meetings with governments across the Balkans.

Jesse Binnall, a lawyer for Guilfoyle, said the ambassador disputed the authenticity of the messages but declined to provide specifics. He said she had been paid to speak at events before her nomination and “was owed a balance for traveling to and supporting these patriotic events.” Deters said he didn’t owe Guilfoyle any balance.