Could a Kennedy scion with a penchant for online antics be the next face of Manhattan’s Upper West Side in Congress?
Jack Schlossberg, the 32-year-old grandson of John F. Kennedy, is mulling a run for the House seat soon to be vacated by retiring Democratic Rep. Jerry Nadler, though his lack of political experience and eyebrow-raising social media behavior have sparked both intrigue and concern among observers, New York Post reported.
Schlossberg, son of Caroline Kennedy—former U.S. ambassador to Japan and Australia—and artist Edwin Schlossberg, boasts an impressive pedigree with degrees from Harvard Law and Business Schools in 2022. Yet, his resume in public service is thin, a point Nadler himself has highlighted in dismissing him as a serious contender.
Before even officially registering as a candidate, Schlossberg has set up an exploratory committee for the 2026 race. His potential bid follows Nadler’s recent announcement that he won’t seek re-election after 17 terms representing the Upper West Side.
But it’s not just lineage that defines Schlossberg—he’s carved a niche as an online provocateur with 707,000 Instagram followers. Posts mocking family members like Robert F. Kennedy Jr., now Secretary of Health and Human Services, and even his late grandmother Jackie Kennedy Onassis, have drawn ire and comments urging him to “seek help.”
Take his bizarre query about whether Usha Vance, wife of Vice President JD Vance, was “hotter” than his grandmother—it’s the kind of stunt that makes one wonder if he’s running for Congress or clicks. Still, a September 3 poll on Instagram showed over 90% of 30,700 respondents cheering him to run, suggesting his antics might oddly endear him to some.
Schlossberg’s political footprint is minimal, though he did work as a staff assistant for the Department of State during his mother’s ambassadorial stint in Japan from 2013 to 2017. He’s also made appearances alongside family, like meeting Prince William in Boston in 2023 with his mother and sister Tatiana, an environmental journalist.
Recently, he started a YouTube podcast, “Test Drive Live,” interviewing political figures from his van, including U.S. Senator Chuck Schumer, who appointed him to the America 250 Commission for the nation’s 250th anniversary in 2026. It’s a quirky platform, but does it translate to votes?
He’s also popped up at Georgetown University to court young Democrats and endorsed Zohran Mamdani in a crowded mayoral race featuring heavyweights like former Gov. Andrew Cuomo and Mayor Eric Adams. A Democratic insider noted, “He’s waiting until after the mayoral election before he makes it official,” which hints at strategic caution—or perhaps indecision.
Nadler isn’t leaving the race without a preferred successor, backing Micah Lasher, a Manhattan Assemblyman raised on the Upper West Side with ties to former Mayor Michael Bloomberg. Lasher’s social media presence, however, is a measly 675 followers compared to Schlossberg’s digital army—hardly a ringing endorsement of grassroots clout.
Other contenders like City Council Members Erik Bottcher and Keith Powers, and Assembly Member Alex Bores, are also in the mix for the Democratic primary in June, though no year is set yet. Even Chelsea Clinton’s name surfaced, only for her to swiftly decline interest.
Political strategist Hank Sheinkopf quipped about Nadler’s endorsement of Lasher, questioning its weight given past missteps in other races. It’s a fair jab—backing a protégé doesn’t guarantee a win, especially against a name like Kennedy, however tarnished by tweets.
Schlossberg’s passion isn’t in doubt—he recently posted a video strolling through New York City, critiquing Donald Trump’s media influence amid the suspension of Jimmy Kimmel’s show over controversial remarks. But passion without policy chops might leave voters cold in a district used to Nadler’s seasoned hand.
Ultimately, Schlossberg’s run, if it materializes, will test whether a famous surname and youthful energy can outweigh a lack of experience and a penchant for digital mischief. The Democratic primary could be less about substance and more about spectacle, a trend conservatives might lament as yet another sign of style over seriousness in today’s politics.
