The scion of the Kennedy family has a skeleton. It lurks in the corner of the livingroom of his Chelsea apartment, wearing a silk grey and burgundy robe and a brown fedora that belonged to his grandfather.
President John F Kennedy was famous for going hatless, to the dismay of the hat industry.
“That’s why, you can tell, it looks completely new,” an amused Jack Schlossberg said.
Sitting in front of the skeleton are a few young people with laptops who are busy plotting Schlossberg’s run for Congress. There’s a whiteboard with “Congressman Jack” scrawled across the top, just above a vintage “Our Man Jack” sign from his grandfather’s 1960 presidential campaign.
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The prize Schlossberg seeks is no less than New York’s glittering 12th district – encompassing the United Nations, the Empire State Building, Times Square, Central Park and this modest one-bedroom I’m standing in.
There are framed prints on the wall near a small grey sofa – Audrey Hepburn, William Shakespeare and Kings of Leon, his favourite band. Schlossberg likes to joke that he resembles Hepburn, and he told me that he has loved Henry IV, Part 1 since high school. He recited his favourite passage: “I’ll so offend to make offence a skill; redeeming time when men least think I will.”
It is fitting that Schlossberg (32), loves Prince Hal, who played around until he rejected Falstaff and tankards and decided to act more responsibly and pick up the mantle of his royal family.
Schlossberg has no Falstaff; he says he doesn’t even drink or use drugs. But, like Prince Hal, he has been searching – dabbling in different jobs and personae.
In a sharp departure from the expected path for a Kennedy interested in politics, Schlossberg entered public life by carving out a role for himself as a charismatic – and sometimes pugnacious, crude and off-the-wall – social media personality, amassing just over 1.7 million followers across X, Instagram and TikTok. Many young people were excited to have another eligible Camelot heart-throb with a thick head of dark hair, this one madly oversharing.
If Schlossberg has been offending to make offence a skill, like Prince Hal, he is also redolent of Hamlet, who feigns being crazy to carry out a serious mission (and ends up doing some crazy things).
On social media, Schlossberg sparred, trolled and went on the attack, often feuding with family members. He explained issues such as gerrymandering and posted arguments against president Donald Trump’s initiatives, sometimes using accents to play different people from different classes. He passed on dating advice from his mother, Caroline Kennedy. He engaged in all kinds of high jinks, making videos where he acted like “a silly goose”, as he said, doing ballet and skateboarding while reciting Lord Byron’s She Walks in Beauty.
His brand of humour confused some people, as when he pretended to be the lawyer for actor Justin Baldoni. He was also just playing a character when he talked about suffering heartbreak or told his followers he had gone out dancing.
“I have never been clubbing,” he told me solemnly.
His mother, who is very private and not on Instagram now that she’s no longer an ambassador, noted that her son had identified social media as a weakness in the Democratic strategy. “I’m impressed that he’s thought through the different ways of doing that and is willing to take the consequences when he takes a risk that people find offensive,” she said.
Schlossberg’s great-grandfather, Joseph Kennedy, was the OG media influencer, figuring out a formula for alchemising his family’s great hair, great teeth and lace-curtain glamour into political power.
Schlossberg has built an enthusiastic following – and appalled some people – on Instagram, TikTok and, briefly, on a YouTube series this year where “the mission” was to drive around the country in a van and “get the truth out there”. In the description of the now-dormant show, he said it would be “serious – and insane. Just like me”.
But then an unexpected opportunity popped up: Jerry Nadler, the liberal stalwart who has represented much of Manhattan in Congress for more than three decades, announced his retirement.
Nadler is likely to back his long-time aide and protege, state assembly member Micah Lasher. Lasher also once ran the Albany office for Michael Bloomberg, who is said to be strongly supportive.
When reports surfaced in September that Schlossberg might run, Nadler brushed off the idea on CNN, saying his successor should be someone “with a record of public service, a record of public accomplishment – and he doesn’t have one”.
Oddly enough, the disapproval from the establishment makes Schlossberg an insurgent. And his campaign operation reflects that, with no sign of high-priced strategists or pollsters. He said he trusted his own judgment – and his mother’s.
The two are “incredibly close”, as Caroline Kennedy put it, and he has helped her with her duties at the Kennedy Foundation and spent time with her during her diplomatic tours of Japan and Australia. In Japan, Schlossberg had brief stints working at Rakuten, an ecommerce company, and Suntory, the distillery made famous by Bill Murray in Lost in Translation.
He is the only grandson of JFK, but don’t call him Prince Jack. “I always shudder when I hear royalty associated with our family,” he said. He mentioned his forebear John F Fitzgerald, the politician known as Honey Fitz (“He picked up a clipboard and organised Irish people in Boston”), adding: “I think that they were really public servants in the end.”
Nonetheless, some online have nicknamed Schlossberg “the People’s Princess”.
The slender six-foot-two candidate went to Yale University, where he volunteered as an emergency medical technician (EMT). “I definitely realised it would be best for everybody if I didn’t pursue a career as a doctor,” he said. From there he got a joint law and business degree at Harvard University. After he passed the bar exam in 2023, he boasted in an interview with People, “I scored 332 in New York state, which may have put me in the top 1 per cent of test takers.”
But he didn’t want to practice law. He took a gig in a surf shop in Hawaii and, during the 2024 election, emulated his glamorous late uncle John Kennedy jnr by trying journalism and writing seven opinion pieces for Vogue.
His entry into the congressional race will reveal, in the wake of the wake for the Cuomo dynasty, if the Kennedys are still a potent political brand. When Joe Kennedy III, a former member of Congress from Massachusetts, tried to unseat senator Edward J Markey in 2020, he got trounced in large part by young progressive voters. And the alliance of Schlossberg’s cousin Robert F Kennedy jnr with Trump has soured the family name for many Democrats.
He does not agree with those in the Kennedy orbit who think it’s too early for him to run. JFK was 29 when he was elected to Congress, Schlossberg noted. “Teddy was 30 when he was a senator,” he said. “It hasn’t always just been all old people, old guard.”
His bookcase contains a biography of JFK by his speech writer, Ted Sorensen. Schlossberg picked it up after a teacher at Collegiate, an all-boys prep school in Manhattan, was irritated that he was not paying attention during a lesson on the Kennedy administration and was ignorant of JFK’s policy in Laos. That set Schlossberg off on a quest to study his grandfather’s history; he began listening to JFK’s speeches after school. “That was a huge awakening,” he said.
On the day after Zohran Mamdani was elected mayor of New York City, I interviewed Schlossberg at the boathouse that serves as the starting point for his stand-up paddleboarding sessions on the Hudson.
He said he thought Mamdani’s triumph was a positive omen for his own campaign. The 34-year-old democratic socialist had won the votes of 65 per cent of men and 82 per cent of women younger than 30, and Schlossberg is confident that he would be good for a district that is a map of his life. He was raised on the Upper East Side and went to school on the Upper West.
He endorsed Mamdani early, before other reluctant Democrats, and defended him against allegations of anti-Semitism. “New York needs to be a safe place for Jewish people,” said Schlossberg, who was raised Catholic and whose father, artist and designer Edwin Schlossberg, is Jewish. “I’m very sensitive to the Jewish community’s concerns, because I feel them, too. It bothers me.”
He said that his paternal grandfather, Alfred Schlossberg, worked in the Empire State Building. “He was in the schmatte business,” he said. “He made men’s dress shirts. His wife’s sisters owned a hat shop on 91st and Broadway. I think that I’m a Schlossberg, too, and from this district. This is my home. This is where my family has lived for generations.”
I asked him how he will earn the votes of those who think he is merely entitled.
“I’m certainly proud of my family’s legacy in public service,” he said. “President Kennedy inspires me. My uncle Teddy fought for healthcare, immigration, labour, which are still the issues of our time.”
Campaigning for Democrats the last couple of years, he said he realised that “we need to specifically elect people who both get policy and know how to break through in new media, because it’s a toxic, polluted ecosystem, thanks to the president.”
I wondered if he was nervous about campaigning in a political landscape sulphurous with violence, particularly given his family history.
“I try not to think about those things,” he said.
Schlossberg became an online presence when he was toying with being an actor like his cousin, White Lotus star Patrick Schwarzenegger. His cameo as a police officer on Blue Bloods was as far as he got. “I auditioned for a few things, a show on a streamer playing a cowboy or something, and didn’t get any parts,” he said. “But I believed in myself as a performer. That led me to the social media realm.”
Some posts are whimsical; others brutal. In one, he introduces viewers to a crab he finds while paddling in the Hudson, before sending “Sebastian”, as he calls the crustacean, on his way. In another, he extols the joys of autumn, urging viewers to “bundle up” and share “harvest season” with friends.
Other posts are designed to provoke and have been criticised by some followers as “misogynistic”, “manic”, “unhinged” and “bizarre”.
Some of his worst attacks have been reserved for his cousin, the secretary of health and human services. In an Instagram video, after lobbing vicious insults at RFK jnr, he said: “I have got a challenge for you. Me and you. One on one, locked in a room, we hash this out. Nobody comes out until one of us has autism. What do you say?” In another video, since deleted, he imitated his cousin’s static-y voice, a condition of spasmodic dysphonia.
To the dismay of some in the family, he hounded his other cousins for not attacking RFK jnr soon enough or vociferously enough. At one point, he posted: “There’s only one Kennedy family – MINE!!”
He has also directed crude insults at Cheryl Hines, RFK jnr’s wife, and ripped into Megyn Kelly, who had criticised the Kennedys who were criticising RFK jnr. Citing her positions on transgender issues, he demanded that Kelly prove she was not a man by showing her sexual organs. He used the “c” word to describe them. Kelly declined to comment.
After I told him that some of his videos made me recoil, he said, “Have I made some mistakes? For sure. We are in uncharted territory.”
I asked if his approach was too Trumpy, at times, as when he belittled his targets’ appearance or mocked his cousin’s voice.
“I feel like he can handle that,” Schlossberg replied.
RFK jnr’s daughter Kathleen fired back at him in February, telling the New York Post: “I hope he gets the help he needs.”
Schlossberg was unfazed. “I love that,” he said of her comment.
It’s one thing for Trump to use such a provocative, sometimes vile, online approach, because people know him. But voters don’t know Schlossberg. How will they distinguish between what’s real and what’s performance art?
He insists that he knows, as Hamlet said, a hawk from a handsaw. “Since I started making videos, people have been calling me crazy, but there’s been a strategy and method to what I’ve been doing,” he said.
He continued: “First of all, if somebody thinks I’m crazy because they saw one of my videos, that means that they saw one of the videos, which means that they got some information about the Trump administration and politics that they might not otherwise have gotten. Second of all, I trust people. I have confidence that people understand what’s going on.”
Becoming a creature of social media has made Schlossberg worried about how tech companies manipulate our minds. “These platforms are being controlled by a handful of individual people,” he said, “and they are the biggest propaganda tools the world’s ever known.”
He hasn’t shied away from getting into Insta-feuds with other celebrities. In April, he lunged at Anna Wintour, for whom he had worked, urging people to boycott the Met Gala (which he attended in 2017 with his mother), saying the times were too dire for such an event. He accompanied his post with a picture of himself as a toddler, naked and peeing from a balcony while wearing Wintour-esque sunglasses.
At age three, Schlossberg was the ring-bearer in John Kennedy jnr and Carolyn Bessette’s wedding at Cumberland Island, Georgia – “I remember I saw an armadillo run by” – and John nicknamed him “Jack-o’-lantern.” As an adult, he has mirrored his late uncle’s gestalt – the shirtless, muscular, man-about-parks – in his social media persona.
But, as with his grandfather, the hale image is a bit of a mirage, built on pain and grit. During his first year in law school, while playing basketball, he went in for a layup and felt something in his back. “I could barely walk for another 4½ years after that,” he said.
Even as he worked, sometimes remotely, to earn his Harvard degrees during the pandemic, he was in pain and anguish with his back – a medical issue JFK also struggled with.
“I thought, ‘I’ll never paddle again, I’ll never surf again,’” Schlossberg said. “I just couldn’t even imagine doing anything, like having a real life.”
He underwent two hip procedures. He got the skeleton, now in his apartment, to study anatomy. His bed comprises two massage tables covered in shark-patterned sheets that he has had since eighth grade.
Caroline Kennedy said the surgeries and intensive physical therapy added up to “a super painful” and “solitary” experience for her son. “It was quite isolating but I think it built a lot of inner strength,” she said. He found a Pilates teacher named Sharyl M Curry who “gave me my life back”, he said.
Schlossberg said he could not have become an online personality during the 2024 campaign “if I hadn’t built the confidence that I could pull myself out of something like that and work my way out of it. No matter what, nothing is as bad as not being able to move.”
If he wins Nadler’s seat, he would be returning to the Capitol, where he once worked as a Senate page for his uncle Teddy and family friend senator John Kerry.
How does he spend his free time? “I paddle, I do ballet class. I don’t really party. I don’t drink. I don’t smoke.”
He doesn’t like clubs or restaurants. He cooks simple things like eggs and steak for himself. He said he’d be happy just eating mayonnaise out of a jar.
He roots for the Yankees, the Knicks, the Liberty, and the Giants, sort of, noting: “I’ve never been huge on football.”
His middle name is Bouvier, and his “silly goose” videos have led several writers to compare him to “Little Edie” Bouvier, Jackie’s flamboyant, kooky cousin who lived at Grey Gardens, the Hamptons estate, with her mother, “Big Edie,” and a clowder of cats.
He said he has no pets but would like to get a fish. As we left the pier, I asked him if he felt more like a Bouvier or a Kennedy.
“I feel like Jack Schlossberg,” he said.
This article originally appeared in the New York Times
