Μake us preferred on Google

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.

A U.S. Embassy official said, “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.”

At a press conference in Athens on Wednesday, Secretary of State Marco Rubio praised Guilfoyle, who sat in front of his podium. “Suffice it to say, our embassy is doing a great job,” he said. “Our ambassador has been a strong ambassador.”

Deters, a 63-year-old attorney and former co-owner of Snappy Tomato Pizza, a regional restaurant chain, mounted unsuccessful runs for Congress and governor. He said in a series of interviews that Guilfoyle’s lack of results left him disenchanted with the Trump administration, even though he mostly supports its policies.

Deters said Guilfoyle told him if he came up with the Amex money, “I will be your Trump ride or die, forever and ever.” But, he said, “she never came through on anything.”

Morning radio

As a morning AM radio host in Ohio, Deters lent his voice to the Trump movement, boosting the 2016 outsider’s campaign. He liked to say he was “Trump today, Trump tomorrow, Trump forever.”

A lawyer nicknamed “the Courtroom Bulldog” in local media, Deters has faced his own legal issues. In 2020, he was banned from entering a courthouse in Ohio’s Hamilton County after threatening on social media to burn it down. The Kentucky Bar Association twice suspended him, citing aggressive litigation strategies, false statements in court proceedings and filing frivolous claims.

When the Kentucky Supreme Court was considering whether to reinstate him to the bar, Deters denounced members of the association as “jokes of human excrement.” The chief justice wrote in 2021, in a ruling not to reinstate him, “Deters’ practice of law is not governed by constitution, rule of law or procedure. It is anarchy.”

“These rules that are written by Big Law to hurt people like me—screw them,” Deters told the Journal, saying he retired as a lawyer. “I am a legal outlaw.”

Deters said his dealings with Guilfoyle began in 2020, when he launched an event called Freedom Fest in Kentucky in response to Covid-19 medical mandates. He paid her $300,000 over the coming years to speak there, he said, adding that he also paid $200,000 in speaking fees to Trump Jr. and $100,000 to Eric Trump. He also gave $125,000 to a political-action committee supporting the president in 2022, according to Federal Election Commission records.

In September 2024, Guilfoyle and Trump Jr. were both scheduled to be in Kentucky to speak at Deters’ event. Trump Jr., traveling on a separate plane, landed at a private airport a half-hour away from Cincinnati’s main airport, where Guilfoyle disembarked. Deters picked her up and raced across southern Ohio—at one point bumping down a grass hill after missing an exit—so she could catch up with the Trump scion. Deters said Guilfoyle nicknamed him “Jason Statham,” after the Hollywood action star.

After Trump won the election that fall, Deters says he began soliciting Guilfoyle’s help on several matters of great importance to him: He wanted the Justice Department to seek the extradition of Abubakar Atiq Durrani, an Ohio doctor who had fled to Pakistan after being charged with defrauding insurers by performing unnecessary spinal surgeries, including on children. And he wanted to talk to incoming Internal Revenue Service Commissioner Billy Long to discuss a probe into his tax deductions.

Deters, who says he is advising lawyers representing hundreds of former patients who are suing Durrani alleging medical malpractice, negligence and fraud, told Guilfoyle he hoped the Justice Department, under Trump, would push Pakistan to find and extradite him.

The case brought Deters in conflict with the doctor’s Indiana-based malpractice insurer, MedPro Group, which has taken the position that it isn’t liable in cases of willful misconduct. In a lawsuit, MedPro accused Deters of “a calculated scheme to extract payments” from the insurer, “at first through abusive litigation, and by ultimately outright extortion through threats of violence and murder and by blackmail against the company’s CEO.”

In an interview, Deters denied the accusations, calling it “the most ridiculous BS lawsuit of all time.”

He said he asked Guilfoyle to have the Justice Department launch an investigation into MedPro.

He told Guilfoyle he would pay her $1 million if she helped him land an interview on former Fox News host Tucker Carlson’s show—where he hoped to draw attention to his cause.

Guilfoyle assured Deters she was working to get him in front of Carlson. “We should hear something by the end of the week,” she wrote in December 2024.

Text messages reviewed by the Journal show Guilfoyle reached out to people in Carlson’s orbit about setting up an interview with him for Deters. It didn’t go far.

Carlson told the Journal he’d never heard of Deters and doesn’t keep up with Guilfoyle, who doesn’t have a role influencing which guests he selects: “A million dollars for a podcast appearance? Isn’t she the ambassador to Greece? This is completely nuts.”

Guilfoyle’s attorney, Binnall, said: “Ambassador Guilfoyle will never apologize for offering to help shed light on a case in which 1,000 children underwent unnecessary, invasive, and debilitating surgeries at that man’s hands.”

Beyond that, Deters and a local guitarist had written a song called “Kentucky Outlaw,” and wanted Guilfoyle to get the lyrics to country-rapper Kid Rock: “He’s a Kentucky outlaw/He fights the man and refuses to crawl.”

Then there was a tax matter he wanted to discuss with the incoming IRS commissioner.

The IRS was questioning a deduction Deters claimed in 2020 related to the sale of his interest in the family business. Deters saw it as politically motivated.

Guilfoyle’s interactions with Deters grew more frequent in the months after she was nominated as ambassador to Greece in December 2024. She promised to lobby top Trump officials from FBI director Kash Patel to former Attorney General Pam Bondi.

“Every secretary of you know defense, transportation, treasury commerce IRS commissioner everyone gets right back to me,” she wrote, before adding the FBI director, his name misspelled: “Oh yeah, l’m forgetting cash Patel.” An FBI spokesman said she didn’t lobby Patel. Other agencies didn’t respond to requests for comment.

Guilfoyle also expressed concern about her dealings with Deters becoming public—and the effect that could have on her ambassador post. She warned Deters repeatedly not to commit talk of money or payments to text. “Eric, I really wish you would stop papering all these things,” she wrote in one exchange.

In January 2025, weeks after her nomination, she complained that Deters had told a producer on her podcast about their deal. “It’s unbelievable when we have a private arrangement with you that you would now CC a producer talking about money,” she said. “Do not say we have any arrangement.”

She added: “What a nightmare you’ll literally cost me my ambassadorship stop writing.”

MAGA icon

Guilfoyle began dating Trump Jr. halfway through his father’s first term and emerged as one of the president’s most outspoken defenders.

After Trump’s 2020 defeat, Guilfoyle sought to turn her status as a MAGA icon into a profitable business, trying her hand at ventures including lines of hair care and fragrance products and a medspa. She also launched a political consulting firm and sought work in public relations.

In 2022, she launched what she termed an upscale vodka and champagne brand, American Dream, organizing a dinner for Mar-a-Lago guests that participants realized halfway through was an investment pitch.

In March 2024, American Dream sought to raise $2 million from investors, according to a pitch deck viewed by the Journal. It projected reaching $75 million in revenue within three years. She later dissolved the company.

Guilfoyle’s lawyer previously told the Journal that “the claim that an American Dream dinner was an ‘investment pitch’” was false.

Trump during this period grew frustrated with Guilfoyle for soliciting investments from Mar-a-Lago members for her companies, according to people familiar with the matter. At one point, he complained that Guilfoyle was supposed to be raising money for him but instead was at his club raising money for herself, according to one of the people.

As her confirmation hearing approached in 2025, Guilfoyle complained to friends that she was broke, people familiar with the matter said. Her engagement to Trump Jr. had ended the previous year. In her financial disclosure in February 2025, she reported liabilities including a boat loan valued at $100,000 to $250,000 and a mortgage valued at between $1 million and $5 million. She also reported assets including a medspa and a new vodka company, each worth between $1 million and $5 million, and reported earning nearly $800,000 in podcast income.

She wanted to sell the Florida mansion she and Trump Jr. had bought years earlier for $9.7 million, but couldn’t find a buyer at the $30 million listing price. (Trump Jr. bought her out of their house for $7.6 million this year.)

Last March, when Deters inquired about when she would move to Greece, Guilfoyle told him to stop asking. “I have a lot shit to get done before then and I need to make money,” she wrote, according to a text reviewed by The Journal.

Later that spring, she began requesting additional payments from Deters. Guilfoyle asked him to draft a letter saying he owed her two $50,000 back payments for consulting services, Deters told the Journal: “She was worried about legality, and she was worried about the appearances of it.”

In a June 11, 2025, letter, reviewed by the Journal, Deters wrote that his consulting company owed Guilfoyle $50,000 “before your new position” and wanted to engage her until her confirmation. “We appreciate your willingness to give us insight and guidance on issues you are uniquely qualified to assist us on,” he wrote.

That same month, Guilfoyle sent a congratulatory note to Long after his confirmation as IRS commissioner. She attached a letter Deters had written outlining his tax dispute: “Don Jr. and I are very close with Eric Deters and his wife and I know he sent you a letter,” she wrote. “I am hoping I know how busy you are that you could give some time and attention to it.”

Two days later, Deters sent her a photo of a printed memo addressed to her: “I have paid you $300,000 over the years,” he wrote. “As of this memo, I have not received one favor. I am not naive or a sucker. I need results.”

In response, she told Deters to “stop papering all these things. It’s really dangerous.”

“Just call me on signal,” she wrote.

As for Long, she would call him the next day, she assured Deters. “I wrote him a very nice message. Told him how important it was that you’re close to me and to don.”

“Also very privately,” she continued, “if you write an email or a text about, l’m gonna kill you cause I love you but you’re so out of control.”

That afternoon she texted an update: Long had written her back.

“BOOM,” she added.

A week later, on July 3, she placed two missed calls to Deters’ phone, and sent him instructions on how to wire money to an American Express account.

“Your needing $100,000 urgent unfortunately is not going to work,” he wrote. “I can’t do this without getting a divorce.”

“I’ve been calling you for over a week straight,” she replied. “You could be here meeting with Billy Long.”

Long is now the U.S. ambassador to Iceland. Embassy officials there referred reporters to a State Department media office that didn’t respond to a request for comment.

Write to Dana Mattioli at dana.mattioli@wsj.com , Drew Hinshaw at drew.hinshaw@wsj.com , Rebecca Ballhaus at rebecca.ballhaus@wsj.com and Joe Parkinson at joe.parkinson@wsj.com