John Kennedy

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.

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