Guilfoyle Never Mastered the Art of the Shakedown

By Froma Harrop

October 15, 2026 5 min read

About three weeks before Republicans expect an electoral beating, Donald Trump had to get rid of Kimberly Guilfoyle, his ambassador to Greece. He simply had to.

Trump's money-grabbing corruption was wearing thin even on devoted fans, but the president knew how to wrap his mob-like patter in foggy euphemisms and double meanings.

Guilfoyle was not good at it. Not at all.

The mob rarely threatens reluctant targets outright. It says things like: "Nice place you've got here. Shame if something happened to it." Or "Do me a favor," as in Trump's 2019 call seeking dirt on Joe Biden from Ukrainian President Volodymyr Zelensky: "I would like you to do us a favor, though."

When confronted with an incontrovertible fact, Trump claims ignorance. He said he didn't know about the $130,000 payment to porn star Stormy Daniels. As for sexual predator Jeffrey Epstein, Trump said, "I barely knew him." Trump's name appears in the Epstein files more than 38,000 times.

This week, Trump almost denied knowing Guilfoyle. "She, I guess, dated my son a long time ago." Guilfoyle and Donald Trump Jr. had been engaged for about four years.

As president, Trump had real power to back up his grifts. Guilfoyle had connections to that power, which she waved around with zero discretion and awe-inspiring vulgarity.

At the Davos gathering, Guilfoyle bragged about her buddy-buddy ties to two Greek tycoons who were paying for her luxury travel around Europe.

Already a Trump family nuisance, Guilfoyle wasn't invited to a dinner run by Greek House Davos earlier this year in honor of Trump's son Eric. She was recorded saying to an American businessman on the guest list: "You know, I can deliver the world to you. Which you deserve. I'm going to make you a lot of f——ing money."

She later said in her disjointed way, "You don't have the f——ing U.S., you know, ambassador to Greece not come. She (the organizer) should be kissing my f—-ing ass."

All this was reported in The Wall Street Journal, which has become America's leading journalistic enterprise. The Journal had earlier reported on Guilfoyle's attempted shakedown of Eric Deters, co-owner of a successful regional pizza chain and unsuccessful candidate in Kentucky for Congress and governor.

Deters wanted Guilfoyle's help with, among other things, stopping an Internal Revenue Service probe into his tax deductions. Guilfoyle texted hm with a request to covertly pay off $100,000 she owed on her American Express card: "Honey please I need you to get this done for me today."

If Deters followed through, she also told him, "I will be your Trump ride or die, forever and ever."

Needless to say, Deters was himself no class act. He had been disbarred from practicing law in Kentucky. When he tried to get reinstated, and ultimately failed, he called members of the state bar association "jokes of human excrement." When banned from entering the Hamilton County (Ohio) courthouse, Deters threatened on social media to burn the building down.

A fine state of affairs the United States finds itself in. In exchange for a $100,000 payoff, Guilfoyle offers to help a known grifter succeed in his latest grifts via her connections to the kleptocracy theme park known as the Trump administration.

Before Trump made her ambassador, he was reportedly annoyed that she was soliciting money from Mar-a-Lago members to invest in her various ventures. He sternly informed Guilfoyle that she was supposed to be raising money for him.

When news broke this week that Guilfoyle had "resigned" as ambassador to Greece, Trump told reporters, "I mean, I don't know. She's an ambassador ... She was always very nice."

That's how it's done.

Follow Froma Harrop on X @FromaHarrop. She can be reached at [email protected]. To find out more about Froma Harrop and read features by other Creators writers and cartoonists, visit the Creators webpage at www.creators.com.

Photo credit: Hans Reniers at Unsplash

Like it? Share it!

  • 0

Froma Harrop
About Froma Harrop
Read More | RSS | Subscribe

YOU MAY ALSO LIKE...