John Oliver Roasts Schumer for Decades of Stories About Fictional New Yorkers Named ‘the Baileys’

Oliver: “But I actually want to talk less about Chuck Schumer himself and more about two of his favorite people, Joe and Eileen Bailey. They’re a couple that, throughout Schumer’s career, he has talked about a lot.”
[Clip starts]
Schumer: “They’re a middle-class couple in Massapequa, which is a suburb on Long Island. (...) Joe and Eileen Bailey, this middle-class couple, they bought into Reagan republicanism in 1980. (...) Joe and Eileen are worried about losing their jobs or their friends’ jobs. (...) The Baileys really don’t believe in trickle-down. They don’t believe in a whole lot of government spending, but they believe in tax breaks for kids to go to college. (...) He’s an insurance adjuster and lives in the New York suburbs. By New York standards, he makes $50,000 a year. If he lived in the middle of the country, he’d make $40,000. Wife works in a medical office. She makes about $20,000. She might make $15,000 elsewhere. And, you know, I have guided my political life through the Baileys.”
[Clip ends]
Oliver: “The Baileys have guided Chuck Schumer’s political life, which is a little weird given they don’t exist. (Laughter) Seriously, he invented them. 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. In it, he mentions the Baileys an astonishing 265 times in 264 pages. (Laughter) But he’d apparently been talking about them for years before the book was published. One of his former spokespeople said he’s always asking, what would the Baileys think? And, to be fair, Schumer acknowledges that some may find this a little weird.”
[Clip starts]
Schumer: “If you ask my staff, I’ve been talking about and talking to the Baileys for 15 years. I have conversations with them. One of my staffers once said I had imaginary friends to the press. Got me in some trouble. But these people are real, and I respect them, and I really love them, and I care about them.”
[Clip ends]
Oliver: “OK, sure, but they’re literally not real, Chuck. (Laughter) (Applause) But even if you can understand the potential utility of creating a prototypical voter in your head, this goes way beyond that, because Schumer’s given the Baileys an unnecessarily detailed backstory. For instance, he said Joe takes off his cap and sings along with the national anthem before the occasional Islanders game. OK. And when their daughter Megan — oh yeah, they’ve got kids, by the way — told Eileen a friend was caught cheating on a quiz, Eileen was appalled because lying is not tolerated in the house ever. Also, Eileen apparently helps with the clothing drive at her church, and her father had a prostate cancer scare a few years ago. Again, this is a made-up family. None of these people exist. But wait, I’m still not done. Apparently Joe Bailey would never have a goatee. They watch ‘Sex and the City’ and ‘Desperate Housewives,’ though Joe pretends not to like either show. They think most baseball players probably take steroids, and if they were to ever go out to a Chinese restaurant, they would order Kung Pao chicken. That is a J.R.R. Tolkien-level of gratuitous backstory, and I don’t say that lightly. But the Baileys do seem to have a lot of Sway over Schumer’s politics, as he’s brought them up when discussing everything from the 2008 financial crisis to cybersecurity, which he framed as protecting the security the Baileys feel when they go online to buy birthday presents. And to hear Schumer tell it, the Baileys’ views can be complicated.”
[Clip starts]
Schumer: “The Baileys are not anti-immigration, but they are anti-illegal immigration. They really dislike the Enron executives who stole money, but they hate the people who burned the flag even more. They are pro-choice. They understand that a fundamental decision like that should be made by the individual. But they’re glad their church isn’t.”
[Clip ends]
Oliver: “Really? Are you sure about that? And the more you hear about the Baileys, the more it feels like they represent a very particular slice of the electorate. Schumer said that they supported the civil rights and anti-Vietnam War movements because they understood that morality was on the side of the protesters. But, starting in the late 60s, when those protesters cursed the returning veterans and Stokely Carmichael advocated armed resistance against the white ruling class, the Baileys were lost. Which, fun fact, is both a misleading history of the civil rights movement and what people who never supported it tend to say. And yet Schumer will insist the Baileys’ concerns are widespread and that they could just as easily have been the Ramirezes of Port Chester, the Kims of Elk Grove, California, or the Salims of Dearborn, Michigan. But crucially, for all he talks about how much he loves the Baileys, they don’t seem to return that love. Because in 2021, he explained how the Baileys had voted in the past few presidential elections.”
[Clip starts]
Schumer: “They voted for Clinton and then they voted for Bush. They’re not a member of one party or another. They’re independent.”
KLEIN: “Did they vote for Donald Trump?”
Schumer: “Both of them did in 2016. Joe Bailey still did in 2020 with misgivings. But she didn’t.”
[Clip ends]
Oliver: “Yeah. (Laughter) The Baileys voted for Trump. And just this March, a Reporter actually got an update on their voting history.”
[Clip starts]
Garcia-NAVARRO: “You said the Baileys voted for Trump in 2016. They split Trump-Biden in 2020. I’m wondering who they voted for in 2024.”
Schumer: “Probably voted for Trump. Probably voted for Trump. But if you ask them why, I think they’d say, above all, crime.”
[Clip ends]
Oliver: “OK. So, to recap, of the six votes the Baileys had across the last three presidential elections, five went to Donald Trump, most recently because of crime, which, for what it’s worth, was down in every category last year, with violent crime at its lowest rate in 20 years. They also think the civil rights movement went too far and aren’t against immigration, just illegal immigration. And this is the couple who, in Chuck Schumer’s own words, have guided his political life. And at this point, it might be worth asking, is that a good idea? Because the truth is, Schumer’s devotion to his imaginary friends may help explain why he and the Democratic Party have been so underwhelming in recent years. Because he seems to be focusing a huge amount on the interest of the Baileys from Long Island, while forgetting other voters actually exist. And look, I’m not saying that you shouldn’t think about how his messaging plays with suburban middle-class voters with pretty right-of-center views, or that they’re not theoretically winnable in the future, what I am saying is, by tailoring your policies so heavily to them, you are pulling yourself to the right. And in doing so, could be alienating not only the rest of your base, but new voters looking for a party that speaks for them. So, Senator Schumer, at least when it comes to formulating policy, 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.” (Laughter)