John Oliver tackles Guilfoyle claim, drug shortages and salutes Skydance

John Oliver opened his latest Last Week Tonight with an alleged $100,000 credit-card favour involving the United States ambassador to Greece, and ended it by pledging loyalty to his new owners. The HBO programme mixed a Washington scandal, a look at generic medicines, and one last joke about who signs the cheques.

The Washington segment, reported on 12 October 2026, focused on Kimberly Guilfoyle, the Trump-appointed US ambassador to Greece. Trump donor Eric Deters, who previously ran unsuccessfully for governor of Kentucky, alleges Guilfoyle asked him to pay her $100,000 American Express bill days before her confirmation, according to text messages obtained by The Wall Street Journal, as reported by Variety. Deters says he came forward because Guilfoyle allegedly promised him a Fox News interview and help getting a song he wrote to Kid Rock in exchange for the money.

Oliver discussed those claims before his main story. During the segment he also brought in Liberty Mutual's Liberty Biberty mascot for a gag built around scandalous fanfic imagery.

He saved his deep dive for something else entirely. His main story, meaning the long reported section that anchors each episode, covered generic medications and national drug shortages.

Then came the sign-off. Oliver closed the programme by saying: "I'm thrilled to be part of the Skydance family! Hope you're happy with what you bought, guys! We're never gonna change!"

Skydance Corp. is David Ellison's newly formed company comprising Paramount Skydance and Warner Bros., which puts HBO's owner inside a bigger corporate house. Oliver has been joking about the takeover for months. He said in March he was not thrilled about getting a new "business daddy" if Paramount won the bid for Warner Bros., then in September called Ellison his "soon-to-be business daddy," according to reports from The Hollywood Reporter.

For the team making the show, there is some certainty. Oliver extended his contract to stay with Last Week Tonight through 2027, as reported by The Hollywood Reporter. HBO lists the programme under Comedy, Variety, Talk and Sketch and credits it with 32 Emmy Awards wins, according to HBO.

For fans, this means the pattern holds. Oliver can tease the owner on air while staying in the same slot.