In a column published by Alternet, Robert Reich — a professor of public policy at the University of California, Berkeley, and former U.S. secretary of labor — poses what he calls a trivia question: Who solicited money from a presidential donor in return for access to the head of the Internal Revenue Service 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, raised money for and spoke at the rally that led to the attack on the U.S. Capitol, and now serves as a U.S. ambassador?

His answer: Kimberly Guilfoyle, now the U.S. ambassador to Greece — a figure Reich describes as uniquely enmeshed in what he terms the dysfunctions of the current political-economic-media-influence system.

Details of her dealings were reported by The Wall Street Journal in an article by Dana Mattioli, Drew Hinshaw, Rebecca Ballhaus and Joe Parkinson. According to the report, President Donald Trump grew frustrated with Guilfoyle for soliciting investments from Mar-a-Lago members for her own companies, complaining that Guilfoyle was supposed to be raising money for him but was instead at his club raising money for herself.

From Fox News to the ambassador's post

Guilfoyle was married to Gavin Newsom, now the governor of California, from 2001 to 2005. 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. She also raised money for and spoke at the rally that preceded the January 6, 2021, attack on the U.S. Capitol.

After Trump's 2020 defeat, Guilfoyle sought to turn her status into 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.

A donor, the IRS and a promised $1 million

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 for governor — began soliciting Guilfoyle's help on several matters. These included 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 Trump Jr.'s former fiancée. Deters promised to pay her as much as $1 million if she was successful.

Her engagement to Trump Jr. ended in December 2024. On December 10, 2024, Trump nominated Guilfoyle to be U.S. ambassador to Greece. Like the IRS commissioner's post, the ambassadorship requires Senate confirmation.

'I need you to get this done for me today'

After Billy Long was confirmed as 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, "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 she needed Deters to pay it in a way that would not leave a paper trail. "It won't show up anywhere if you wire money to American Express," she wrote on Signal, an encrypted messaging app, 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 episode, Reich writes, illuminates what he describes as the casual pay-to-play world in which Trump, his family, his appointees and his donors operate.

Lawmakers call for an investigation

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 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 United States could undermine the Greek government if it chose to, that she promoted the business interests of one particular Greek construction and energy company, and that she allowed its lobbyist into private diplomatic meetings. The two panels have jurisdiction over U.S. diplomacy and American ambassadors abroad, and whether their scrutiny extends to the Deters episode — the promised $1 million, the outreach to Long and the $100,000 request — remains to be seen.

In Reich's view, being close to power in Trump's world creates a special economy of getting and giving, with arenas spanning Fox News, Mar-a-Lago, the White House, Capitol Hill and U.S. embassies abroad — and in which all relationships, whether personal, romantic, political or diplomatic, are transactional.

His writings can be found on his Substack newsletter.