John Oliver devoted the opening of Sunday’s “Last Week Tonight” to Kimberly Guilfoyle, the Trump ambassador to Greece who is now under investigation by the State Department’s own watchdog. The probe centers on allegations that she pressed a MAGA donor to pay off her $100,000 American Express bill days before her confirmation.
The HBO host called the scandal “pretty tacky” and read from messages first reported by The Wall Street Journal. In them, Guilfoyle told donor Eric Deters on Signal that a wire to American Express “won’t show up anywhere,” and wrote, “Honey please I need you to get this done for me today.”
“Okay, first, that text is something,” Oliver said, before spinning out his own version, per The Daily Beast: “Pumpkin, please also send 100 grand to Sephora. I need a new vat of charcoal eyeliner. My style icon is a raccoon.”
Oliver said Deters, a former lawyer, radio host and one-time co-owner of the Snappy Tomato pizza chain, wanted favors in return, including help with the IRS and a slot on Tucker Carlson’s show. Deters has said he also wanted Guilfoyle to get Kid Rock to hear a song he wrote.
“Do you know how bad a song has to be for it to be not good enough for Kid Rock?” Oliver quipped.
He also revisited Guilfoyle’s 2020 Republican National Convention speech, saying she was “one step away there from transforming into a flock of crows.” He joked that her teleprompter at a Fourth of July embassy event must have told her to deliver her lines like a Disney animatronic running out of battery.
Asked about Guilfoyle on Friday, President Trump told reporters, “Too bad! I mean, I don’t know,” adding that “she was always very nice.”
Deters has called the arrangement a quid pro quo and says he never sent the money. Guilfoyle’s attorney has disputed the authenticity of the messages without offering specifics. Former White House ethics czar Norm Eisen called the texts among the worst he had seen from a U.S. ambassador.
Oliver closed by noting that the White House is considering removing her from her post, then played a clip of her convention catchphrase: “The best is yet to come!”
Oliver was far from alone in criticizing the revelations. Tommy Vietor, a former Obama national security spokesman and Pod Save America co-host, focused on Guilfoyle’s apparent indifference to a paper trail. He posted on X: “I cannot get over how f—ing stupid @kimguilfoyle is. Babe!!! Stop documenting our crimes!! Signal me babe!!! Crime me on Signal!”
Conservative writer and Atlantic staff writer Tom Nichols took a more somber tone, writing that “the grifting is bad enough, but the grubby vulgarity of it all should embarrass every American.”
The Dispatch co-founder Stephen Hayes said he wasn’t “sure I’ve read a story over the past decade that better captures the grifter culture of TrumpWorld better than this one,” calling it “jaw-dropping, and yet none of it is really surprising.”