Troll Jack Schlossberg planning to run for Jerry Nadler’s House seat and experts say he has ‘a shot’

The grandson of John F. Kennedy Jr. is mulling a run for Congress in Manhattan, and he may have “a shot” at winning the Democratic primary next year, according to political observers.

Jack Schlossberg, 32, is best known for his online trolling of various prominent people and unhinged social media posts.

He has impersonated First Lady Melania Trump and frequently rails against his cousin, Robert Kennedy Jr, the Secretary of Health and Human Services. At one point he imitated RFK Jr.’s spasmodic dysphonia, which sometimes makes it difficult for him to speak.

He is said to be eyeing Democratic Rep. Jerry Nadler’s seat on the Upper West Side after the 17-term Congressman decided earlier this month that he would not seek re-election in 2026.

Schlossberg has told his social media followers he had set up an exploratory committee but has not yet registered to run.

“He’s waiting until after the mayoral election before he makes it official,” said a Democratic party insider who is close to the Kennedy scion.

For veteran political strategist Hank Sheinkopf, the plan makes sense. With the city focused on the four-way race with controversial Democratic candidate Zohran Mamdani leading the poll against former New York governor Andrew Cuomo, Mayor Eric Adams and Guardian Angels chief Curtis Sliwa, Schlossberg might have to back a candidate if he announces a national campaign before the November vote.

“It’s a smart move,” said Sheinkopf. “Why put pressure on him to engage in the mayoral race and force him to have to fake a position to back a candidate he may not want to back?”

Instead, Schlossberg is warning the Democratic party needs fundamental change and feels his confrontational style will get people’s attention.

Last week, when Jimmy Kimmel’s late night program was suspended after the host’s comments about slain conservative activist Charlie Kirk, Schlossberg posted a video message to his Instagram account showing him walking through New York City, talking about Donald Trump’s “media presidency.”

“Democrats need to to come up with something quickly because if we don’t get our act together and fight back on the airwaves with a better message spoken to people in ways they can understand…if we don’t do that and we let another election cycle go by without giving anyone anything to cheer for, we’re going to keep losing,” Schlossberg said. “We’re running out of time.”

However, Schlossberg’s troll-like online behavior has left many of his followers concerned, with some even telling him to “seek help.”

In one post he mocked his late grandmother, Jackie Kennedy Onassis, questioning whether Usha Vance, Vice President JD Vance’s wife, was “hotter” than his grandmother.

“I called my grandmother hot … have I totally lost it? Jesus … this kid will do anything for attention. Your grandfather would be ashamed. Seriously. Time to get a job,” he wrote.

In trying to appeal to young voters, he made a guest appearance at a Georgetown University meeting of campus Democrats and last month started “Test Drive Live,” a YouTube podcast where he interviews political leaders from his van.

US Senator Chuck Schumer was one of his first a guests. During the podcast, Schumer announced that he had appointed Schlossberg to the America 250 Commission, a non-partisan charity organizing events for the commemoration of the 250th anniversary of America’s founding on July 4, 2026.

Schlossberg recently asked his more than 707,000 Instagram followers if he should run for political office. More than 90 percent answered “yes” and 30,700 responded to the poll, according to the Sept. 3 post.

Schlossberg, who’s full name is John Bouvier Kennedy Schlossberg, graduated from both Harvard Law School and Harvard Business School in 2022.

He is the son of Caroline Kennedy, a former US ambassador to Japan and Australia. His father, Edwin Schlossberg, is an artist. He has two older sisters — environmental journalist Tatiana Schlossberg and artist Rose Schlossberg.

The young Kennedy has little personal political experience, as recently pointed out by Nadler who dismissed Schlossberg as a serious candidate, saying he lacked any public service experience, according to reports.

“If I were Jack, I would think that means he could win,” said the Democratic Party source, referring to Nadler’s dismissal. “Besides that, he’s unlike any other Kennedy. He’s trying to find himself and that resonates with voters and is humanizing.”

In the Democratic primary race for his seat, scheduled for June, Nadler is backing his political protegé Micah Lasher, a newly minted Manhattan Assemblyman.

Lasher, who was born and raised on the Upper West Side, has 675 followers on Instagram.

“He’s got almost no social media presence,” said the Democratic source.

“I’m not sure Nadler’s endorsement is valuable,” said Sheinkopf. “He’s constantly backed Scott Stringer in the mayor’s race. Is Stringer the mayor?”

In addition to Lasher, New York City Council Members Erik Bottcher and Keith Powers as well as Assembly Member Alex Bores have also expressed interest in Nadler’s seat.

Chelsea Clinton had also been floated as a candidate for Nadler’s seat but has since said she is not interested in running, according to City & State.

If Schlossberg — who did not return a request for comment from The Post — is hoping to run on the Kennedy legacy, his campaign could backfire, said Sheinkopf.

“He’s a guy with a German-Jewish last name who still has the patina of the Kennedys even though you have to stop to explain who he’s related to,” Sheinkopf told The Post.

“That legacy is really questionable now. But he brings passion, he brings youth. And the electorate might not care that he has no experience.”

Schlossberg worked with his mother, Caroline Kennedy, when she was ambassador to Japan from 2013 to 2017, accompanying her on official visits and working as a staff assistant for the Department of State.