Democratic influencer Jack Schlossberg is hoping to be the next Kennedy to be elected to public office — but will the luster of his family’s political dynasty be enough to make up for his thin resume and trail of bizarre online behavior?

The only grandson of President Kennedy announced Tuesday his plans to represent New York’s 12th Congressional District, a seat being vacated next year by Democratic veteran Jerry Nadler.

“I’m not running because I have all the answers to our problems,” said Mr. Schlossberg, 32, a lifelong New Yorker, in a video announcement. “I’m running because the people of New York 12 do. I want to listen to your struggles, hear your stories, amplify your voice, go to Washington and execute on your behalf.”

Mr. Schlossberg promptly launched a polished, official campaign website under his slogan, “Jack for New York,” pitching himself as part of a “new generation” of political leadership in New York ready to counter President Trump’s agenda. “This is our last chance to stop Trump — it won’t come again,” Mr. Schlossberg writes on his site’s front page. “History is calling. Will we answer?”

His campaign materials leave no doubt about the source of Mr. Schlossberg’s political capital, with frequent references to his family legacy. Listing his full name — John Bouvier Kennedy Schlossberg — he credits his civic commitment to “the example set by his family and by the city that shaped him.” One campaign photograph shows Mr. Schlossberg bears a striking resemblance to his late uncle, John F. Kennedy Jr., a resemblance he leans into in campaign photos, including one in which he posted on a bicycle (John Jr., who died in a plane crash in 1999, was known to wander Manhattan on his bike). In the photo, Mr. Schlossberg even copies Kennedy’s trademark backwards cap, bike lock, and rolled-up pants leg.

Mr. Schlossberg is the only son (and one of three children) of Caroline Kennedy, the only surviving child of the 35th president.  Ms. Kennedy, who endorsed Barack Obama at a crucial point in the campaign, in a New York Times opinion essay entitled “A President Like My Father,” was rewarded with the ambassadorship to Japan and then, under President Biden, the ambassadorship to Australia.  

Mr. Schlossberg is making his bid for public office at a time when the Kennedy family’s power is greatly diminished. No Kennedy currently holds elective office, and the family was humiliated when, in 2020, Massachusetts  Senator Ed Markey beat off a challenge from Rep. Joseph P. Kennedy III, the first time a Kennedy lost an election in Massachusetts. Robert F. Kennedy Jr., Caroline’s cousin, holds a position of immense power as an unusually prominent secretary of Health and Human Services, but he is despised by his family who have publicly denounced him.

Mr. Schlossberg, by contrast, is believed to be in good standing with his extended family, but his professional resume is thin, even for a 32 year old. After attending elite schools — the Collegiate prep school in Manhattan, then Yale, and Harvard Law and Business Schools — he did some Washington internships and was named  a political correspondent for Vogue magazine for the 2024 election  (he published a handful of articles). He has made a name for himself, however, as a social media influencer, boasting an impressive following of more than 1.7 million across his main platforms.

His social media presence doesn’t fit the mold of what you might expect from an up-and-coming politician, with his posts ranging from shirtless selfies to ballet videos to inflammatory political commentary. Many of his more outrageous, deleted posts (which are easily recoverable) are now being recirculated. 

An outspoken critic of President Trump, Mr. Schlossberg has made controversial statements about members of his administration, including Vice President Vance and his wife, Usha Vance.

One post that drew particular blowback came on Mr. Trump’s inauguration day, when Mr. Schlossberg asked his followers on X: “True or false: Usha Vance is way hotter than Jackie O,” comparing the vice president’s wife to his own grandmother. He later posted a bizarre Instagram video in which he professed his love for Ms. Vance, calling her “the most beautiful woman in the world” and asking her to be his “Valentine.” He also posted a meme suggesting jokingly that he’d fathered a child with her.

Mr. Schlossberg has also targeted Harvard Law School professor emeritus Alan Dershowitz, accusing him of killing his own wife among other unfounded claims. “Everyone knows I killed my wife, I’ve got a thousand sexual assault cases against me, I look like a human penis. I’m completely irrelevant and I’ve never had consensual sex … Oh wait, s***t, that’s you,” Mr. Schlossberg stated in one strange video tirade, prompting Mr. Dershowitz to threaten a defamation lawsuit.

Perhaps his most frequent target is his mother’s cousin, Robert F. Kennedy Jr. Mr. Schlossberg has mocked Mr. Kennedy’s speech impediment — caused by the muscular disorder, spasmodic dysphonia — and at one point joked that Mr. Kennedy’s “energy ball” recipe was made of “Jew blood (Ashkenazi not Sephardic).” The tasteless remark was probably a botched effort to mock his mother’s cousin for propagating a discredited conspiracy theory that the Covid vaccine was designed in a lab to spare Ashkenazi Jews (who are 70-80 percent of the world’s Jewish population).

Mr. Schlossberg is known to delete his posts soon after sharing them and has on several occasions deactivated his social media profiles altogether. This past February, after sharing a flurry of offensive posts, Mr. Schlossberg suddenly deleted both his Instagram and X accounts with a cryptic message: “I’m sorry to everyone I hurt. I was wrong. I’m deleting all my social media. Forever. It’s been fun. Thanks anyways everyone.” Internet sleuth, however, have had little trouble finding the posts.

Although the social media personality claims his outlandish postings represent a deliberate strategy to drum up attention for real political issues, his erratic habits have sparked speculation about depression or mental instability. Entire Reddit threads have been formed to discuss Mr. Schlossberg’s social media activities, with users questioning at times whether he’s had a “mental breakdown” or a “crisis.”

It remains to be seen whether Mr. Schlossberg will be able to convince New York City voters he is a serious candidate, though it looks like he might have his work cut out for him. A generous New York Times profile released on the day of his campaign announcement was inundated with negative comments, with many readers doubting whether he is up for the task.

“‘No kings’ also means: No princelings, no hereditary aristos, no dynasts. The last thing America needs is to perpetuate yet another generation of this would-be ruling house,” reads one of the top-recommended comments. “We don’t need a rich, trust fund kid with no experience,” another reader wrote. “Sounds perfect, three Ivy League degrees, a few days of work and a social media expert. Should save the nation!” quipped a third, adding, “I find this news depressing!”

The race is also shaping up to be particularly competitive. Mr. Schlossberg will be vying for the NY-12 seat alongside State Assemblyman Alex Bores, West Side City Council Member Erik Bottcher, and first-term state lawmaker Micah Lasher — known as Mr. Nadler’s protégé — among numerous other well-qualified candidates.

Mr. Nadler himself has been lukewarm about Mr. Schlossberg’s political ambitions. When asked about his candidacy in September, Mr. Nadler replied: “Well, there’s nothing particularly good or bad about a Kennedy holding my seat. But the Kennedy, unlike Schlossberg, should be somebody with a record of public service, a record of public accomplishment, and he doesn’t have one.”

The outgoing New York congressman further predicted that Mr. Schlossberg “certainly is not going to be a major candidate,” adding, “There will be major candidates.”