The most important thing to know about the 12th Congressional District of New York is that it should not exist. Since time immemorial, Manhattan was divided in half. There was one congressional district anchored on the Upper West Side, extending down the Hudson and across the harbor to pick up Jewish precincts in Brooklyn, and another centered on the Upper East Side and spreading across the East River to cover part of Queens. One side had Zabar’s, Cafe Luxembourg, Columbia University, and the Lincoln Square P.J. Clarke’s; the other, Elaine’s, the Carlyle, Gracie Mansion, and the original P.J. Clarke’s. But when Albany screwed up the decennial redistricting a few years ago and a judge kicked responsibility for the map to a cartographer in Pittsburgh, this poor fellow looked at these two neighborhoods and saw a very small area crammed with people who were very rich, very white, and very old and smushed them together as if Central Park were a mere slice of greenery and not an 800-acre demilitarized zone keeping two distinct peoples apart.

Chaos ensued. Dogs and cats were thrown together in a single Democratic primary that ran river to river from 96th Street to 14th Street. Specifically, Jerry Nadler, a liberal lion of the Upper West Side, and Carolyn Maloney, a Democrat from the Silk Stocking District with a fierce political instinct but who was perhaps best known for wearing a burka on the House floor and trying to bring pandas to the Central Park Zoo. And they did what any two longtime colleagues in their 70s would if forced to compete for the same job: They attacked with a ferocity that could have lit up the Empire State Building (now conveniently smack in the middle of the contested territory). Maloney accused Nadler, a man so of his neighborhood that he showed up at a Donald Trump impeachment session carrying a Zabar’s shopping bag, of being “half dead”; Nadler allies knocked Maloney as a daffy dupe who bought the Bush administration’s lies about Iraq.

The Race to Be the Face of Manhattan

Nadler won in a landslide, a result in part attributable to just how lopsidedly the new district’s Democrats were distributed. (“Texas has oil, and the Upper West Side has Democrats,” Nadler protégé Scott Stringer likes to say, a remark that makes less sense the more you think about it.) Then, three years later, Nadler abruptly — as much as a 78-year-old does anything abruptly — announced he was retiring. A flood of speculation ensued about who might run: Chelsea Clinton, Andrew Cuomo, Cynthia Nixon, onetime Trump fixer Michael Cohen, and writer and literary scenester Molly Jong-Fast were all mentioned, while every city councilmember and state legislator who had ever represented any portion of the district put out word that they too were taking a look. Even Maloney said she was thinking about mounting a comeback.

“New York-12 is it,” says Jong-Fast, who lives there. “This is a district that is D-plus — I don’t know, some crazy number.” It is D 33, which means no Republican has a shot. “It’s as blue as it gets. But it is also a district that went for Cuomo,” she continues. “It’s Democratic but not liberal. It’s a voting base that is very engaged. You’ve got the MSNBC audience, a lot of Jewish voters, so it’s a lot of elements that are important for the Democrats’ struggle with themselves.”

NY-12 is also the smallest and most population-dense congressional district in the country, one that candidates can crisscross several times in an afternoon. It is among the wealthiest and oldest districts in the United States and is also the district with the most college graduates. It is an ATM for Democrats — something Nadler never fully exploited — and is primed for a politician who can make use of the fact that all the major television and cable-news networks, the New York Times, and The Wall Street Journal are based there.

If you listen to the candidates, the battle for NY-12 is not just about who will be the next member of the city’s congressional delegation but a contest among factions of the island’s Democratic base: the old-money elite, the anti-Trump resisters, the tech-world crusaders, and the old-school party Establishment. While nearly a dozen candidates are vying for the seat, the primary is coming down to just four: Micah Lasher, a state assemblyman from the Upper West Side and a longtime political hand who is Nadler’s anointed successor; Alex Bores, an assemblyman from the Upper East Side whose calls for AI regulation have led to millions of dollars being spent both for and against him; George Conway, the onetime Republican lawyer who has achieved notoriety as a leader of the #Resistance; and a previously little-known social-media influencer who is trying to rewrite the rules of New York City politics.

“It’s New York-sized,” that social-media influencer, Jack Schlossberg, said when asked why this campaign is different. He was sitting in a diner near his apartment in Chelsea, eating a late breakfast of a plate of bacon, which he finished before absentmindedly spooning up the grease with his forefinger and licking it. Schlossberg’s presence in the race proves the point. The 33-year-old grandson of John F. Kennedy, son of Caroline, nephew of John Jr., and scion of America’s faded royal family, Schlossberg was previously known to the public mostly from a series of baroque viral videos. In one, he is shirtless and dancing provocatively at the beach, his shorts pulled just below the tan line, his finger perched on his pouty lips. In another, he puts on a wig and pretends to be Melania Trump talking to Vladimir Putin. In a tweet, he asked who is hotter, Usha Vance or Jackie Kennedy — his grandmother, to be clear. He also mused on X about Jesus’ apparent challenges with putting on muscle (“Most popular guy of all time — not jacked. Toned, but not big. So my question is — did Jesus want to put on muscle but couldn’t? Or was he lean on purpose?”). After the hosts of Pod Save America conducted a reputation-washing interview with the leaders of Kamala Harris’s failed presidential campaign, Schlossberg wrote that they should all “Podsave my limp dick.”

When I sat down, I was bracing for an unpleasant meal. In person, though, Schlossberg is little like his online self. “I spent the first 30 years of my life inside a library,” he says. He comes across as serious and smart. Schlossberg graduated from Collegiate, where, according to schoolmates of his, he never talked about his pedigree and it was an unspoken rule not to bring it up. From there, he went to Yale, then to a job in Tokyo with Suntory, the liquor company, and then to a posting at the State Department while his mother was ambassador to Japan. After that, he earned a dual business-and-law degree from Harvard. (None of this would be in evidence from his LinkedIn, which lists his current job as “Director of the CIA” and his work experience as “Special Assistant to Lauren Boebert” and a flight attendant with Pan Am; Harvard Law is noted, but Schlossberg says his role there was “dermatologist.”)

The social-media antics were, in his telling, just a way to crack the algorithm. Clout is the coin of the digital realm, and the way to get it is by getting attention. While, early on, most other members of the Kennedy clan thought it unseemly to publicly criticize Robert F. Kennedy Jr.’s increasingly conspiratorial musings and eventual Trump alliance, Schlossberg tore into his cousin, whom he told me he barely knows. In a series of Instagram videos, Schlossberg assumes various personas, including that of a Masshole for whom RFK Jr. is despoiling the family name (“You know, I’m a fan of his father. And you know his uncle? Rest in peace, I remember where I was the day he was killed. I mean, it was a tragic day, the entire country wept. But listen, that guy, he’s a prick. The new guy, the young guy, he’s a friggin’ prick”).

“Jack stood out as someone willing to stick his neck out,” says a senior Biden campaign official. “Everyone else was concerned about protecting the Kennedy brand. It looked completely unhinged to me, but there was a method to the madness.”

By the time Schlossberg showed up at the Democratic National Convention in 2024, where there were special-access passes for influencers, he was mobbed by fans. “I had this experience where, although I grew up in a famous family, I myself wasn’t recognizable or famous. People started recognizing me everywhere I went,” Schlossberg says. “I couldn’t go anywhere at the DNC without getting swarmed, and I realized that I get how to do this so that people respond to it.”

Schlossberg endorsed Zohran Mamdani two weeks before the mayoral primary, the only NY-12 candidate to do so (Lasher and Bores endorsed him after the primary), and there’s a Zohran-like vibe to his campaign events, minus the ideological fervor. One Sunday morning in late March, I went to a party Schlossberg hosted at a Tenth Avenue pizzeria. Eighty people showed up — all of them new to any Schlossberg event — and another 150 were on the waiting list. A strong majority were women under 30. As Schlossberg made his way from table to table, they gazed at him dreamily.

I spoke to one woman who was a freelance choreographer, another who was a graduate student, and another who worked at Trader Joe’s after being laid off from a museum job. Many were new to New York and to politics, and many lived outside the district but were looking for something to get excited about. No one cared about Schlossberg’s lack of experience — many were looking for jobs themselves — and all mentioned some connection (usually from a mother or grandmother) to the candidate’s famous family.

“This is way more fun just being on your phone and talking shit,” Schlossberg said at the end of the event, standing on a table to address the crowd. “We can win. We are running against someone who is taking money from billionaires, hand over fist, and saying that they’re gonna go to Washington and fight corruption. What a joke. We’ve got another guy who says that he’s gonna regulate AI. That sounds nice, and then he goes and he takes a million dollars from an AI company. All we want is for you guys to come here, make friends, and then, when you leave, go to the polls in June and vote for Schlossberg.”

In addition to the young demographic, Schlossberg does well with famous people. A few weeks later, at a meet and greet at Chez Nous, a French restaurant in the back of the Marlton Hotel in Greenwich Village, Amy Sedaris, Rick Moody, Michael (son........

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