Jimmy Kimmel is using Kimberly Guilfoyle’s own words against her.
The MAGA figurehead was outed this week in a bombshell report about a bizarre grift. The 57-year-old was exposed for asking a donor to cover a $100,000 American Express bill in 2025, just days before she was confirmed as Donald Trump’s ambassador to Greece.
In several messages, she asked for money from Eric Deters, a MAGA donor, former criminal defense attorney, and former owner of the restaurant chain Snappy Tomato Pizza.

Guilfoyle’s insane demand has rocked Capitol Hill and Kimmel jumped on the story during his Thursday night monologue. The late-night host and Trump nemesis stitched together pieces of Guilfoyle’s past as a long-time Fox News personality.
“Our ambassador to Greece was begging the owner of Snappy Tomato Pizza to pay her credit card bill. This person was asking for a handout,” Kimmel laughed, panning to Guilfoyle’s many conversations on Fox.

In these clips, the former fiancée of Donald Trump Jr. is seen saying, “Nobody likes freeloaders” and “Give people, you know, a hand up versus a handout.” This seems to be a theme in her rhetoric.
Discussing Chicago teachers on strike, she said, “They’re acting like petulant, like little brats because they’ve been rewarded with higher salaries.” In another instance, she cries, “Pay your bills yourself, work hard, get a job as a waitress or whatever.”
Her hypocrisy didn’t go unnoticed by the laughing audience. Kimmel responded, “Now, in fairness to Kimberly, she has a lot of expenses. I mean, she’s looking at around 30 grand a month just in eyeliner alone. Lip filler is not cheap. It costs a lot of money to look like a disappointed bullfrog. You know, she really does, by the way. I mean, this woman is physically evolving into the alt-right mascot Pepe the Frog.
“Don’t worry, Kim. When they fire you, and they make you come home, we got a nice green reflecting pond for you to live in,” he continued. “I never thought I’d say this. Don Jr. might have been the smart one in the relationship.”






