Standing backstage at a darkened, half-filled club in Midtown Manhattan, Caroline Kennedy tried to seem cheerful on Tuesday night, even as it became apparent that her son, Jack Schlossberg, would fall far short in his bid to win a House seat.
“I think he’s done a great job,” Ms. Kennedy said of her son, praising his passion and eloquence, adding that she believed he had no regrets about his candidacy. “He just said he wouldn’t be able to live with himself if he didn’t try. Because he’s so concerned about what’s going on.”
Minutes earlier, the crowd — perhaps a hundred supporters, many young and some from outside the New York City district Mr. Schlossberg had hoped to represent — sat mostly quiet as Mr. Schlossberg rushed through a brief speech, reading from a stack of papers. He joked about his age, led a chant of “Let’s go, Jack” and nodded to perhaps the most famous quote from his grandfather, John F. Kennedy.
“All of us asked not what our country can do,” Mr. Schlossberg said as he finished his speech, “and what we can do to help our city.”
He did not concede in his speech, and still had not by night’s end. But the results were clear: Mr. Schlossberg would not be going to Congress.
For a first-time candidate, Mr. Schlossberg seemingly had it all: a scion of the Kennedy family, once America’s most famous political brand. Young and handsome, much like his grandfather, the progenitor of Camelot.
He was well connected, earning endorsements from Democratic royalty like the former House speaker Nancy Pelosi, and old-money rich, able to pour his own fortune into a campaign he said was, in part, about the evils of money in politics.
And in an age in which Democrats have often played catch-up with Republicans online, Mr. Schlossberg had a vibrant social media presence, presenting an oddball and decidedly opinionated persona that drew attention whenever he posted.
When early polls showed him in front of a crowded field of candidates in New York City’s 12th Congressional District, it seemed the race was Mr. Schlossberg’s to lose.
As it turned out, he lost it.
Once considered a favorite, Mr. Schlossberg, 33, landed in third place in a Democratic primary in one of the nation’s most liberal districts, now held by Representative Jerrold Nadler, the veteran Democrat, who is retiring. Micah Lasher, an assemblyman who had been endorsed by Mr. Nadler, won the primary.
It’s an open question whether Mr. Schlossberg’s defeat signifies the demise of a decades-long political dynasty or simply a setback for a family for whom tragedy and accomplishment have been meted out in equal measure. But the rejection of Mr. Schlossberg, the only grandson of the former president, is undoubtedly a rebuke of the most influential line of the Kennedy family tree.
For some observers, the time was simply not right for another Kennedy to be anointed, particularly one like Mr. Schlossberg, whose quirky online presence seemingly gave birth to a chaotic campaign, plagued by staff turnover, missed meetings and a rotating set of advisers.
“He was seen as somebody who was very entertaining,” said Hank Sheinkopf, a longtime Democratic political consultant, “but not necessarily serious.”
Mr. Schlossberg’s defeat also comes as the Kennedy family has also grappled with the defection of Robert F. Kennedy Jr., Mr. Schlossberg’s cousin, to a Republican administration, where he serves as the health secretary under President Trump.
Known for his opposition to vaccines and other elements of modern medicine, that Kennedy has become an ardent supporter of the president, appearing alongside Mr. Trump at events like an Ultimate Fighting Championship cage match at the White House last week.
Several family members have spoken out about Robert F. Kennedy Jr., including Mr. Schlossberg and his sister, Tatiana Schlossberg, who wrote an acclaimed and agonized New Yorker essay late last year about her terminal cancer, criticizing the health secretary for cutting “nearly half a billion dollars for research” on possible lifesaving vaccines while she fought the disease.
Ms. Schlossberg’s death in December, at 35, came just weeks after the start of her brother’s campaign. In a statement to The New York Times in May, Paige Phillips, his campaign manager, said that Mr. Schlossberg had been running for office “amid a deeply, deeply personal tragedy.”
Chris Coffey, a Democratic consultant, said that he felt bad for Mr. Schlossberg, likening his campaign to Andrew Yang’s unsuccessful mayoral bid in 2021, which Mr. Coffey managed. Mr. Schlossberg, who has never held elective office, seemed unsubstantial, he said.
“He just looked erratic,” Mr. Coffey said. “Jack didn’t have a message other than, ‘It’s time to shake up politics.’”
Mr. Coffey added that his campaign had picked up some important endorsements, including Ms. Pelosi’s, but that the candidate had struggled to articulate a clear position on Israel’s military actions in the Middle East, an issue that has divided Democrats, as well as those on the right wing.
More than anything, however, Mr. Schlossberg — running as both an outsider and, conversely, a well-sourced insider — may have suffered from a lack of nuts-and-bolts ground game in a district that girdles the center of Manhattan and includes some of the city’s most affluent neighborhoods.
“There was a lot of excitement and flash early, but when the dust settles, the folks who you would have expected to do well went to their coalitions and relied on their political experience,” Mr. Coffey said. “Jack didn’t have a base.”
Those sentiments were echoed by State Senator Liz Krueger, who lives in the district and said of Mr. Schlossberg that “we didn’t see him on the streets very much.” She endorsed Assemblyman Alex Bores, who was in second place on Tuesday.
Ms. Krueger said people in New York’s 12th District would ask her for her thoughts on candidates. “But no one ever even started a discussion with me about Jack,” she said, adding, “He did not break through.”
She added that while Mr. Schlossberg’s social media presence might have attracted young supporters, it did not necessarily connect with the many older voters who populate the Upper West Side and Upper East Side, two large chunks of the district.
Mr. Schlossberg poured at least $1 million of his own into the campaign, and had tried to press his case in its closing weeks, including in a lengthy interview with The New Yorker, where his sister’s final essay had been published. Even here, though, his answer to why he was running for Congress seemed somewhat generic.
“I’m running because I want to pass laws,” he told David Remnick, the magazine’s editor. “I want to pass laws that help the people in this district and in our country.”
Mr. Sheinkopf, the consultant, said that Mr. Schlossberg’s defeat might have something to do with the fading legacy and allure of the Kennedys.
“He probably thought that social media, plus his Kennedy relationship, and being a grandson of a former president and having the imprimatur would be something that New Yorkers would pay attention to,” he said, noting that the assassination of President Kennedy, and effectively, the end of Camelot itself, had occurred more than 60 years ago.
Still, he believes that Mr. Schlossberg’s career in politics is probably far from over.
“He’s quite gregarious, and he’s pleasant and friendly,” he said. “That tells you that he’s got a future. But not a present.”
Back at the Cutting Room, the Midtown venue where Mr. Schlossberg’s Primary Night party was held, the candidate said it had “been the honor of my life to work with this group of people.” He added, “If we win tonight, or if we don’t, we’re still in the midst of a corruption crisis.” He left soon thereafter.
For her part, Ms. Kennedy recalled that she had encouraged her son to run, saying: “Our country’s really got a problem. And our election system is really messed up.
“So you absolutely should go for it,” she recalled saying.
And she, too, suggested that maybe Mr. Schlossberg could be back, ending the conversation with two words.
“Stay tuned,” she said.
