Pay to Play to Play to Pay

Friends,

Here’s today’s trivia question (which may turn out to be not at trivial at all when all the facts emerge): Who solicited money from a presidential donor in return for access to the head of the IRS over the donor’s taxes, was a Fox News host, was engaged to the son of the U.S. president, was the former wife of someone who wants to be the next U.S. president, who raised money for and spoke at a rally that led to an attack on the U.S. Capitol, and now is a U.S. ambassador?

If you guessed Kimberly Guilfoyle, you’d be correct on all counts.

Rarely has a person been so enmeshed in the workings (or one might say, dysfunctions) of our current political-economic-media-influence system as Guilfoyle.

From 2001 to 2005, Guilfoyle was married to Gavin Newsom, now governor of California. In 2018, she began dating Donald Trump Jr., became engaged to him in 2020, and emerged as one of his father’s most outspoken defenders and a MAGA icon.

After Trump’s 2020 defeat, Guilfoyle sought to turn her status into a profitable business 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.

According to a report in yesterday’s Wall Street Journal by Dana Mattioli, Drew Hinshaw, Rebecca Ballhaus, and Joe Parkinson, Trump grew frustrated with Guilfoyle for soliciting investments from Mar-a-Lago members for her companies, and complained that Guilfoyle was supposed to be raising money for him but instead was at his club raising money for herself.

The Journal reports that after Trump won the 2024 election, Eric Deters — a Trump donor and former co-owner of Snappy Tomato Pizza, a regional restaurant chain, who had mounted unsuccessful runs for Congress and governor — began soliciting Guilfoyle’s help on several matters, including gaining access to incoming Internal Revenue Service Commissioner Billy Long, to discuss an IRS probe into Deters’s tax deductions.

Guilfoyle offered to use her sway as Donald Jr.’s former fiancée. Deters promised to pay her as much as $1 million if she were successful.

Her engagement to Trump Jr. ended in December 2024. On December 10, 2024, Trump nominated Guilfoyle to be the U.S. ambassador to Greece.

After Billy Long was confirmed IRS commissioner, Guilfoyle sent him a congratulatory note, attaching 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.”

She assured Deters that “I wrote him a very nice message. Told him how important it was that you’re close to me and to don.”

The Journal reports that as her confirmation hearing approached, Guilfoyle complained to friends that she was broke.

She reached out to Deters with an urgent request: She needed $100,000 that she said she owed American Express — and needed Deters to give it to her 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 Journal.

“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 ultimately did not make the payment, But the set of transactions illuminates the casual pay-to-play world in which Trump, his family, appointees, and donors all operate.

The Senate confirmed Guilfoyle as ambassador to Greece on September 18, 2025.

Billy Long is now the U.S. ambassador to Iceland.

The top two Democrats on the House Foreign Affairs and Senate Foreign Relations committees have now called for an investigation into Guilfoyle.

Congressional Democrats are already looking into claims reported last month by the Journal that Guilfoyle told guests at a reception that the U.S. could undermine the Greek government if it chose to, that she promoted the business interests of one particular Greek construction and energy company, and allowed its lobbyist into private diplomatic meetings.

In Trump world, being close to power creates a special economy of getting and giving. The arenas include Fox News, Mar-a-Lago, the White House, Capitol Hill, and extend even to our foreign embassies. All relationships within these arenas — personal, romantic, political, diplomatic — are transactional.

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