Standing on a drizzly street corner on the Upper East Side, Jack Schlossberg was running out the final days of his congressional primary campaign in a strange tempest of nostalgia and youthful insistence.
His television ads have featured the decidedly old-guard Nancy Pelosi, the former House speaker, and his mother, Caroline Kennedy. The supporters stopping to take his picture on the Upper East Side were largely either high school students or retirees.
And his culminating event at Terminal 5 — a venue that probably had its heyday with performances by the Arctic Monkeys and My Chemical Romance more than a decade ago — was sparsely attended, filled with plentiful references to his grandfather along with some dabs and Kesha songs for the younger set.
In this high-profile race to succeed Representative Jerrold Nadler, it might have seemed, at first, hard for a rival candidate to overcome the pedigree of a Kennedy scion. But Mr. Schlossberg is running for office in one of the country’s most affluent and influential districts, in a Democratic primary field that includes Mr. Nadler’s chosen successor (Micah Lasher), a candidate who has engendered support and weathered attacks from the artificial intelligence industry (Alex Bores), a yappy never-Trumper (George Conway) and a global vaccine expert (Nina Schwalbe).
After facing revelations about his haphazard, staff-churning campaign and then a precipitous drop in the polls, Mr. Schlossberg, 33, has been trying to wrest back control over the narrative about his candidacy.
He told The Wall Street Journal that his race is about the clash between a scrappy social media native and the forces of dark money — though Mayor Zohran Mamdani’s election told that tale far more clearly. He told supporters that his race is about youthful energy, though Mr. Bores, one of the candidates near the top of recent polls, is 35. He has said that his race is about taking on the billionaires spending big on his rivals and then plowed at least $1 million of his own money as a counterweight.
Much of Mr. Schlossberg’s efforts to make the campaign about something bigger — his family’s legacy, or how his prolific posting can activate a broader progressive base — seem designed to shift attention away from a career path that does not tell much of a clear story about the candidate himself.
“You guys are so focused on the timeline of my résumé,” Mr. Schlossberg said on that day of end-sprint Upper East Side campaigning, at another point adding: “I think the hate we’ve been getting is evidence of how much support we’ve had. And I don’t believe any of the polls.”
Mr. Schlossberg’s relatively brief work history — a short stint as a political correspondent for Vogue, four months as a State Department assistant under Secretary John F. Kerry — has given way to a congressional campaign that splices together a peculiar combination of paeans to old-timey patriotism and Zoomer-skewing provocation. In one light, it is a campaign doused in 1960s sepia; look again, and it is bathed in the uncanny glow of a heavy Instagram filter.
The supporters approaching him as he spent a day shaking hands near early voting sites uptown seemed murky about which half of it was working for them, or really why.
Asked how Mr. Schlossberg had come onto her radar, one volunteer, Robin Shanen, a 72-year-old retiree, said she was taken by his social media presence.
“People who talk about ‘Oh, he’s rich’ — he could be in Ibiza,” Ms. Shanen said, giving the clubby vacation spot an Upper West Side inflection, Eye-Bee-Zah. “He doesn’t have to do this.”
“Obviously he’s nice looking, I mean — he’s taller than I realized,” Ms. Shanen continued. “The Kennedys are not that tall.”
For affirmation, she looked to a 25-year-old campaign staffer, who gazed back quizzically and replied, “Um, yeah, I don’t know exactly.”
“Bobby Kennedy was like 5-foot-10 maybe,” Ms. Shanen pressed on. “And I remember where I was when John F. Kennedy got shot.”
At another point, Mr. Schlossberg’s sidewalk hang attracted a different corner of his base: a pack of high school girls who wanted to take a picture with him. They told the candidate that they were in 10th grade. After he asked how school was going and obliged their group photo request, Mr. Schlossberg asked, “Do you guys have parents that might want to vote?”
Mr. Schlossberg has generally seemed eager to keep the tone of his campaigning light, doling out high fives, flashing thumbs up and recounting the pivot to zany social media posting that built his following.
At a Wednesday evening event for supporters and donors, he was confronted with a question about the coverage of his campaign, which included attention toward his missing weekly strategy meetings or disappearing for long stretches with little notice or explanation.
Mr. Schlossberg used humor to try to partly deflect the question.
“There’s a lot of hostility toward our campaign, even though we’re just trying to help, not trying to force anything down anybody’s throat — just an option, take it or leave it,” he said. “We’re trying to do things differently, and I don’t owe a bunch of favors to people and I’m not controlled by anybody. Other than my mother and father.”
The party that Mr. Schlossberg threw for supporters earlier this month at Terminal 5 had the familiar blend of good-old-days and how-do-you-do-fellow-kids. The playlist included the Pitbull-Kesha collaboration, “Timber” (at least three times), Frank Sinatra and Johnny Cash.
The event was headlined by David Letterman, who poked fun at his own lapsed relevance with a joke about being recognized from “Antiques Roadshow.” The former late-night host said he had made up his mind on his support for Mr. Schlossberg when the aspiring congressman was 16.
Mr. Schlossberg danced onstage with the actress Natasha Lyonne, professed his admiration for former President Joseph R. Biden and promised to be “the most confusing member of Congress you’ve ever seen.” Some in the audience were impressed.
“I think he’s a good guy,” Sean Holleran, 30, said. “I wanted to come support.”
That support, though, has its limitations. Mr. Holleran lives in New Jersey.
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