Comedian John Oliver is fed up with Chuck Schumer’s politics—and his imaginary friends.
For decades, Senate Minority Leader Chuck Schumer has invoked Joe and Eileen Bailey, a fictional Long Island couple meant to represent the average American and serve as the guiding force behind his political decisions.
“The Baileys have guided Chuck Schumer’s political life — which is a little weird given they don’t exist,” Oliver said during his Sunday night monologue on Last Week Tonight.
The HBO host ran through the Baileys’ “unnecessarily detailed,” nonexistent history — and the New York lawmaker’s many, many references to his pretend pals over the years.
The world was first introduced to the Baileys in Schumer’s 2007 book, Positively American: Winning Back the Middle-Class Majority One Family at a Time. According to Oliver, Schumer mentions the swing-voting, middle-class couple an astonishing 265 times in just 264 pages.
“I have conversations with them… one of my staffers once said I had imaginary friends to the press, got me in some trouble,” Schumer says in a clip Oliver played.
Schumer describes the couple as Reagan-era Republicans — socially liberal but fiscally conservative. He’s offered up intricate details about their fictional lives: their love of Kung Pao chicken, Joe’s habit of singing the national anthem at Islanders games, and Eileen’s father’s chilling run-in with prostate cancer.
“That is a J.R.R. Tolkien-level of gratuitous backstory, and I don’t say that lightly,” Oliver joked.
Oliver emphasized just how much sway the Baileys have over Schumer — despite not being real. The senator has referred to the couple when framing his positions on everything from the 2008 financial crisis to cybersecurity.
But despite Schumer’s continued devotion, the Baileys have effectively abandoned him. Oliver points out that, by Schumer’s own admission, the couple voted for Donald Trump in five of the last six presidential ballots cast between them.
“Politically, it seems they’ve already broken up with you,” Oliver said.
In 2020, Schumer says Eileen abstained from voting and Joe voted “with misgivings” for Trump. This time around, both cast their ballots for Trump without hesitation.
For Oliver, the Baileys represent more than just a slice of American life — they also reflect the Democratic Party’s lack of direction.
“Schumer’s devotion to his imaginary friends may help explain why he and the Democratic Party have been so underwhelming in recent years,” Oliver said.“He seems to be focusing a huge amount on the Baileys from Long Island — while forgetting other voters actually exist.”
The Daily Beast has reached out to Oliver and Schumer for comment.






