The scion of the Kennedy family has a skeleton. It lurks in the corner of the living room of his Chelsea apartment, wearing a silk gray and burgundy robe and a brown fedora that belonged to his grandfather.
President 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 Mr. 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.
The prize Mr. 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 gray sofa — Audrey Hepburn, William Shakespeare and Kings of Leon, his favorite band. Mr. 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 favorite passage: “I’ll so offend to make offense a skill; redeeming time when men least think I will.”
It is fitting that Mr. 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.
Mr. 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, Mr. 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 heartthrob with a thick head of dark hair, this one madly oversharing.
If Mr. Schlossberg has been offending to make offense 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, Mr. Schlossberg sparred, trolled and went on the attack, often feuding with family members. He explained issues like gerrymandering and posted arguments against President 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 Byron’s “She Walks in Beauty.”
His brand of humor confused some people, as when he pretended to be the lawyer for the 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,” Ms. Kennedy said.
Mr. Schlossberg’s great-grandfather, Joseph Kennedy, was the O.G. media influencer, figuring out a formula for alchemizing his family’s great hair, great teeth and lace-curtain glamour into political power.
Mr. 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.
Rep. Nadler is likely to back his longtime aide and protégé, the state assemblyman Micah Lasher. Mr. Lasher also once ran the Albany office for Michael Bloomberg, who is said to be strongly supportive.
When reports surfaced in September that Mr. Schlossberg might run, Mr. 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 Mr. 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 Ms. 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, Mr. Schlossberg had brief stints working at Rakuten, an e-commerce company, and Suntory, the distillery made famous by Bill Murray in “Lost in Translation.”
He is the only grandson of J.F.K., 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 organized Irish people in Boston”), adding: “I think that they were really public servants in the end.”
Nonetheless, some online have nicknamed Mr. Schlossberg “the People’s Princess.”
The slender 6-foot-2 candidate went to Yale, where he volunteered as an E.M.T. “I definitely realized 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. 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 percent 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 Jr., 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 congressman 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 Mr. Schlossberg’s cousin Robert F. Kennedy Jr. with Mr. Trump has soured the family name for many Democrats.
“When it comes to Jack,” said Alex Bores, a fellow millennial and New York state assemblyman who is also running for the 12th district seat, “New Yorkers just voted to end one political dynasty with a storied past and troubled present. We’ll see how they feel about another.”
When Mr. Schlossberg’s grandfather and great-uncles were stars of the party, Democrats had the aura of change and idealism. How did that shift to an image of sententiousness?
“I think part of it has to do with losing touch with young people and being complacent,” Mr. Schlossberg said. “When I close my eyes and think of what a Democrat is, it’s someone who’s challenging the status quo, who represents counterculture, artists, innovators. We lost touch with that, I think, because we were scared of what we were seeing from the other side and didn’t quite know how to react to it.”
He does not agree with those in the Kennedy orbit who think it’s too early for him to run. J.F.K. was 29 when he was elected to Congress, Mr. 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 President Kennedy by his speechwriter, Ted Sorensen. Mr. 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 J.F.K.’s policy in Laos. That set Mr. Schlossberg off on a quest to study his grandfather’s history; he began listening to J.F.K.’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 Mr. Schlossberg at the boathouse that serves as the starting point for his stand-up paddle boarding sessions on the Hudson.
He looked more polished than in his videos. He was wearing a crisp blue Oxford shirt, Jil Sander black slacks and Redback boots. His hair has grown out from a buzz-cut he got in solidarity with someone close to him who is sick. And he no longer has fake diamond studs in his ear. (A dance enthusiast, he said he had his ears pierced to appear in a “Pirates of the Caribbean” ballet.)
He said he thought Mr. Mamdani’s triumph was a positive omen for his own campaign. The 34-year-old democratic socialist had won 65 percent of men and 82 percent of women under 30, and Mr. 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 Mr. Mamdani early, before other reluctant Democrats, and defended him against allegations of antisemitism. “New York needs to be a safe place for Jewish people,” said Mr. Schlossberg, who was raised Catholic and whose father, the 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 shmatte 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.”
He disagreed with Mr. Mamdani’s campaign pledge to arrest Bibi Netanyahu if he sets foot in New York, and he chose not to describe the conflict in Gaza as a “genocide.” “I think it’s painfully clear that Israel’s committing atrocities in Gaza,” he said.
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 health care, immigration, labor, which are still the issues of our time.”
Campaigning for Democrats the last couple years, he said he realized 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 sulfurous with violence, particularly given his family history.
“I try not to think about those things,” he said.
Mr. Schlossberg became an online presence when he was toying with being an actor like his cousin, the “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 fall, urging viewers to “bundle up” and share “harvest season” with friends.
He walks along the river lip-syncing Taylor Swift’s “Love Story.” He offers dating advice, telling viewers not to worry if you like someone and they don’t like you back, because “you might not be their cup of tea.”
“I’m not for everybody,” he says. “You know, my mom always said that. She said, ‘Jack, you’re a little different than the other guys.’ And she wasn’t wrong.”
Other posts are designed to provoke and have been criticized 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 R.F.K. Jr., 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 R.F.K. Jr. 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, R.F.K. Jr.’s wife, and ripped into Megyn Kelly, who had criticized the Kennedys who were criticizing R.F.K. Jr. Citing her positions on transgender issues, he demanded that Ms. Kelly prove she was not a man by showing her sexual organs. He used the “c” word to describe them. Ms. Kelly declined to comment.
Last February, he lit into Alan Dershowitz — who was once a lawyer for his uncle Teddy on the Chappaquiddick case — for his association with Jeffrey Epstein, suggesting that he had killed his first wife. An irate Mr. Dershowitz threatened to sue Mr. Schlossberg for defamation.
“Look, he’s obviously a very bright kid,” Mr. Dershowitz said. “I feel sorry for the kid. He’s obviously disturbed. Everybody on the Vineyard feels sorry for him. Generally, when he’s with his mother, he’s well behaved, but then goes off on these wild rants. If he’s going to run, maybe he’s going to control himself and present himself in a more positive way.” But, said Mr. Dershowitz, who has a small apartment on Fifth Avenue in the 12th district, “I won’t vote for him.”
Soon after the Dershowitz kerfuffle, Mr. Schlossberg got off social media, saying, “I’m sorry to everyone. I was wrong. I’m deleting all my social media. Forever.” But a week or so after deleting many of his offensive videos, he was back, bristling away. Now he says he was just “faking my own social media death.”
Mr. Schlossberg also turned off some people when he implied that he was having a baby with Usha Vance and when he asked his followers who was hotter: Ms. Vance or his grandmother, Jacqueline Bouvier Kennedy Onassis?
When the MSNBC host Jen Psaki asked him on her podcast about his remark, Mr. Schlossberg replied by summing up the criticism: “Creepy, weird. Why would he say something like — why did he do that? Isn’t that weird? It’s his grandma.” Then he added: “Well, that’s why I did it. The internet is a place where it’s difficult to break through.”
He explained: “The internet is a nuance destruction machine — there’s no room for qualifying anything, ever. You have to be very controversial to break through.”
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 uncle’s voice.
“I feel like he can handle that,” Mr. Schlossberg replied.
R.F.K. Jr.’s daughter Kathleen fired back at him in February, telling the New York Post: “I hope he gets the help he needs.”
Mr. Schlossberg was unfazed. “I love that,” he said of her comment.
It’s one thing for President Trump to use such a provocative, sometimes vile, online approach, because people know him. But voters don’t know Mr. 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 Mr. 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.
Last summer, he slammed Ryan Murphy, the producer of the anthology series “Love Story,” for making John Kennedy Jr. and Carolyn Bessette the subjects of the show without consulting the family or earmarking some of the profits for the Kennedy Library.
In his attack, he accused Mr. Murphy of taking his uncle’s life and “profiting off it in a grotesque way” and warned that he might visit the set.
“I was messing around,” he told me. “I didn’t actually do it.”
He also made fun of Mr. Murphy’s appearance — “Looks like a thumb,” he said on Instagram — and posted a picture of him from the 2019 camp-themed Met Gala in a bejeweled cape that was a tribute to Liberace. The caption read “pervert.”
“This is a centuries-old vilification meant to condemn and weaponize hate against gay people, and that’s exactly what he did,” Mr. Murphy, who is gay, told me. “And I received threats against my personal safety and that of my family because of it.”
“How is that not disqualifying to someone who is asking to represent what has to be one of the highest concentrations of L.G.B.T.Q. voters in one district?” Mr. Murphy said.
Mr. Schlossberg denied that calling Mr. Ryan a “pervert” had anything “to do with his personal life,” adding: “In my mind, that’s a form of perversion, to be so obsessed with somebody’s sexuality and their love life, to produce a multimillion-dollar series about them.”
At age three, Mr. Schlossberg was the ring-bearer in John and Carolyn’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 four-and-a-half 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 about his back — a medical issue J.F.K. also struggled with.
“I thought, ‘I’ll never paddle again, I’ll never surf again,’” Mr. 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.
Mr. 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.”
When I asked him for some people to call for this piece, he listed Gerry Pefanis, a doorman in the Upper East Side building where he grew up.
“I’m telling you, that guy is a sweetheart,” said Mr. Pefanis, who knew him from the time he was a small boy. He said that Mr. Schlossberg offered to babysit during a weekend when Mr. Pefanis’s wife was away and he had no one to watch his children. “Other kids in the building, they don’t care as long as I get them a taxi and get the door and their packages,” he said.
At the starrier end of his character references was David Letterman, who has been friends with the family since Jack was in middle school at Collegiate.
“Here’s a kid who paddle boards in the Hudson, up and down, dodging traffic,” Mr. Letterman said. “You can’t get more New York than this kid. And his educational accomplishments, good Lord. I went to Ball State and got Cs.”
He said he understood why Mr. Schlossberg used shock value online. “Truthfully, aren’t we at a stage in civilization where, Jesus, what the hell does make a difference?” he said. Of the spicier posts, Mr. Letterman said: “I’m not worried about that, because I think there is a whole swath of the population who understands the difference between being serious and being cheeky. And, by the way, this is the first time I’ve used the word ‘cheeky.’”
I asked Mr. Schlossberg about his romantic life.
“People often wonder,” he said. “I am very straight.” He added that “one day” he would like to get married and have kids.
He tried the exclusive dating app Raya, but got off because “I went on dates for a while and they didn’t really lead me to find love.”
If he wins Mr. 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 Nets, 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.
Confirm or Deny
After the main interviews, Mr. Schlossberg sat for a lightning round Q&A.
Maureen Dowd: The Kushners are the new Kennedys.
Jack Schlossberg: Deny!
Sydney Sweeney’s hot, even if she’s a Republican.
She’s not hot.
As a teenager, you were jealous when your cousin Conor Kennedy dated Taylor Swift.
Deny.
Your biggest crush is Janet Yellen.
Confirm.
You hated it when Kim Kardashian wore the glittery dress Marilyn Monroe wore to sing “Happy Birthday” to your grandfather at Madison Square Garden.
I didn’t care. I didn’t care. I didn’t care.
You agree with Kim that the moon landing was faked.
Deny.
The happiest you’ve ever been is when Dwayne “the Rock” Johnson sent you a birthday greeting.
Confirm.
You think “the Rock” should be president.
He’s too smart to run for president.
Your mom broke with the Clintons and backed Obama after you urged her to — so, in turn, you’re expecting an Obama endorsement.
I’m not expecting anything from anybody. I’m trying to do this myself.
You would have killed for Patrick Schwarzenegger’s role in “White Lotus.”
Never, ever wanted that.
You were upset when Trump plowed over two of your grandmother’s gardens outside the Oval and the East Wing.
I actually think it’s not terrible to redo things. My grandmother and grandfather made changes themselves, and that’s a great thing. We should update it — but that’s not what’s going on here. It’s a ballroom being built with billion-dollar donations from the largest, most powerful companies, and you can tell where Trump’s interests lie. And to me, it was like, oh, he’s definitely going to to try to stay. He is rebuilding the White House. He’s not going anywhere unless he is removed.
Going out to restaurants is corrupting.
Yes. I just don’t like sitting still at a restaurant, waiting for your food. Why is socializing around restaurants? That said, I don’t hate restaurants as much as I used to.
You eat a can of sardines a day.
Just about, yes.
Your pump-up ritual is Red Bull and Creed.
It used to be. Now it’s more Beethoven. Sometimes I drink seltzer or coffee, but I’m laying off the Red Bull.
When you met the activist Lilly Ledbetter, you finagled to get a picture with her.
Yeah, well, Lilly, equal pay.
You still have your first car, a Toyota Tacoma truck.
Yes.
You love to keep flowers in your apartment.
Love. My favorite are carnations. I love lilies, too.
Maureen Dowd is an Opinion columnist for The Times. She won the 1999 Pulitzer Prize for distinguished commentary. She is the author, most recently, of “Notorious.”
The post Jack Schlossberg, Social Media Provocateur, Gives Politics a Try appeared first on New York Times.
