John Oliver Roasts Chuck Schumer For Decades of Stories About Pro-Trump Couple — Who Are Totally Made Up
John Oliver skewered Senate Minority Leader Chuck Schumer (D-NY) for his decades-long fixation on an imaginary Long Island couple – Joe and Eileen Bailey – questioning why the Democratic leader has allowed non-existent voters to justify his political instincts.
In a series of clips from years past, Oliver rolled out the Baileys’ lore, as told by Schumer, on Last Week Tonight. The Baileys, according to the Democrat’s own telling, are a middle-class duo from Massapequa whose political journey began as Reagan Republicans in 1980, socially moderate but fiscally cautious and became his personal bellwether.
“Schumer first introduced the world to the Baileys in his 2007 book, Positively American, winning back the middle-class majority, one family at a time,” the host said. “In it, he mentions the Baileys, an astonishing 265 times in 264 pages. He’s apparently been talking about them for years before the book was published.”
Throughout his career, Oliver continued, Schumer has assigned them a detailed backstory, from Joe singing the national anthem at Islanders games to Eileen’s church clothing drives, their preferred fast-food orders (“Kung Pao chicken”) and favorite TV shows.
But, as Oliver repeated in his Sunday monologue: “They don’t exist.”
“Seriously, he invented them,” the comedian said, mocking Schumer’s Bailey lore by adding: “That is a J.R.R. Tolkien-level of gratuitous backstory, and I don’t say that lightly.”
The problem, Oliver argued, is political. Ultimately, he’s used them time and time again to frame his policy positions on everything “from the 2008 financial crisis to cybersecurity.”
The host continued to jibe how Schumer admitted the Baileys voted for President Donald Trump in five of the last six presidential ballots cast between them in the past three elections. In March, he speculated they “probably voted for Trump” again in 2024.
Oliver’s larger point was blunt: catering policy to the imaginary Baileys risks dragging Democrats rightward while alienating their base.
“It might be time to break up with the Baileys, which really shouldn’t be that hard to do, given that politically, it seems they’ve already broken up with you,” he joked, before segueing into a mock sketch of “the real Baileys,” portrayed as MAGA conservatives mocking Schumer’s attempts to win them over.
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Oliver’s Baileys, however, quickly reveal themselves as far more hardline than Schumer’s centrist archetype.
“We’re Republicans, Chuck. We’re super Republican,” they announce, before rattling off a barrage of grievances.
“I think they’re putting litter boxes in schools,” Joe says, while Eileen adds: “Every time a celebrity dies, I tweet, vaxxed.”
The couple boasts: “I take Ivermectin, every day, out of spite,” rail against store clerks who “don’t say Merry Christmas, even in June,” and demand, “Where’s my straight pride parade?”
Joe then brags: “Oh, I stormed the Capitol!”
By the end, the Baileys put it bluntly: “Our own kids don’t even speak to us, Chuck. You shouldn’t either.”
Watch above via X.
