Schumer's fictional Massapequa family, the Baileys: A joke, or tribute to the overlooked voter?

When the HBO comedy and commentary series "Last Week Tonight with John Oliver" featured a segment on Joe and Eileen Bailey, the fictional avatars of the great American middle class from Massapequa often cited by New York Sen. Chuck Schumer, it got laughs from the studio audience.

From Long Island’s political class, not so much.

"What [Oliver] says is funny, but I don’t think he’s on the mark with this," said Jay Jacobs, chairman of the New York State and Nassau County Democratic parties.

Jacobs said Schumer’s fictional family was borne out of ample time the senator had spent talking to real voters about real concerns on Long Island.

"Schumer spends a lot of time on Long Island," Jacobs said. "I wonder how much time Mr. Oliver spends here."

Suffolk County GOP chairman Jesse Garcia said the Baileys "represent where Schumer’s voters are: They don’t exist — they’re figments of the imagination of a political operative or they’re in some cemetery somewhere in New York City."

Still, no fan

Garcia added, for good measure, that his assessment of the liberal-leaning Oliver’s political acumen was mostly low.

"Celebrity elitists are not in tune with the actual middle class," he said.

Some backstory: In 2007, Schumer published "Positively American," a book with a second half consisting of a platform he hoped Democrats would follow for the next decade. As manifestos go, it was on the tame side, including plans to increase math and reading scores and another to build the nation’s capacity to fight terrorism. The platform, he wrote, was intended to improve the lives of the typical American middle class family.

The first half of the book introduced that family, the Baileys: both 45, swing voters with three children in local public schools and a household income of about $117,000 in today’s dollars. They were "generally optimists" who believed that "people who work hard and play by the rules will do fine in America," though they worried about the rising cost of living and were sometimes skeptical of the nation’s government, which they felt too often focused on the "very poor or the very rich."

In short, the Baileys were Schumer’s political lodestar. "We always had this family in the front of our minds," he wrote. "What would they think about what I was saying or proposing? Would it really make their lives better? How could I convince them that government could be their friend?"

The Oliver segment, broadcast Sunday, featured clips of Schumer discussing the Baileys, in novelistic detail over the course of many years, on news programs and Sunday morning talk shows. In two podcast interviews played in the segment, Schumer even updated their stories to reveal that they had voted mostly for President Donald Trump in the last three elections, casting their 2024 presidential votes for him largely because of fears about crime. (Those fictional votes broadly aligned with Long Island’s political shift toward the right in recent years. In the 2022 midterms Schumer himself underperformed with voters in both Nassau and Suffolk. In the 2024 presidential election both counties broke for Trump — Nassau after having supported Democrats for decades. The Baileys’ hometown of Massapequa was deep red territory in the last three presidential elections.)

The Baileys swing right

Then Oliver threw his editorial roundhouse: "He seems to be focusing a huge amount on the Baileys from Long Island while forgetting that other voters actually exist. ... By tailoring your policies so heavily to them, you are pulling yourself to the right, and in so doing could be alienating not only the rest of your base but new voters looking for a party that speaks for them."

The Baileys, Oliver's segment suggested, were no longer middle-of-the-road apolitical types but instead had become far right Republicans.

Spokespeople for Schumer and Oliver's show did not respond to requests for comment. In an interview, Jacobs said that Schumer’s analysis was truer than Oliver’s.

"Most people on Long Island are middle-of-the-road people who aren’t all that interested in politics but are concerned with affordability ... quality of their kids’ schools, and they’re concerned about public safety."

Garcia said he found the idea of a politician using a fictional couple to make his points objectionable. Schumer, he said, "has once again proven the closest he comes to understanding middle class is fabricating them for the purpose of selling a book or to advocate his own failed policies."

Hank Sheinkopf, the veteran Democratic political strategist, offered Schumer a piece of advice: "He should be talking to the Baileys more than ever, asking people to be rational." The Baileys, Sheinkopf added, are a device that "worked because they are Schumerism. Schumerism is serving the people, getting in the middle as often as possible. It’s entirely constituent-driven. You alienate as few as possible."

By Nicholas Spangler

nicholas.spangler@newsday.comspanglernewsday

Nicholas Spangler is a general assignment reporter and has worked at Newsday since 2010.