If you spend more than five minutes on TikTok, you’ve probably seen him. He’s the 6'2" guy with the messy hair, the jawline that looks like it was carved from New England granite, and a sense of humor that is... well, it’s a lot. People call him "babygirl." He calls himself a "silly goose." But to the rest of the world, he is Jack Schlossberg, the only grandson of JFK and the man everyone keeps trying to cast as the second coming of his uncle, John F. Kennedy Jr.
The resemblance is honestly kind of jarring.
When Jack flashes a smile or stands shirtless on a paddleboard in the East River, the internet collectively gasps because they see the ghost of 1990s Camelot. But here is the thing: Jack Schlossberg isn't just a carbon copy. He’s something much weirder and, frankly, more modern. While JFK Jr. was the quintessential "Prince of America" who navigated the world with a polished, albeit tragic, grace, Jack is out here posting chaotic videos, feuding with Ryan Murphy, and running a 2026 congressional campaign that looks nothing like the Kennedy runs of the past.
The Mirror Image and the Weight of the Name
Born John Bouvier Kennedy Schlossberg, the name alone is a heavy lift. Growing up as the son of Caroline Kennedy and Edwin Schlossberg, Jack was largely shielded from the relentless paparazzi that defined his uncle’s life. But you can't hide those genes. By the time he hit his twenties, the "Jack Schlossberg JFK Jr." comparisons became an inescapable part of his brand.
It’s not just the hair. It’s the vibe.
Both men shared an affinity for the water and a certain athletic, "unbothered" aesthetic. JFK Jr. famously failed the bar exam twice before passing; Jack, perhaps learning from family history, breezed through a joint J.D./M.B.A. program at Harvard and passed the New York bar in 2023. He’s got the credentials. But while his uncle founded George magazine to merge lifestyle and politics, Jack is using Vogue and TikTok to do the same thing for Gen Z.
Why the Comparison Actually Fails
Honestly, if JFK Jr. were alive today, he probably wouldn't know what to make of Jack’s Instagram.
John-John was the ultimate celebrity. He was the most handsome man alive, a guy who could make a bicycle ride through Central Park look like a movie poster. Jack Schlossberg is leaning into a very different type of fame: the "unhinged" intellectual.
He doesn’t want to be your idol; he wants to be the guy in your DMs making a joke about condiments.
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- Social Media Strategy: Jack uses "irony-poisoned" humor to break through the noise.
- Political Tone: He isn't afraid to be "pugnacious" or "crass," as Maureen Dowd once put it.
- Family Loyalty: He’s been the most vocal critic of his cousin, Robert F. Kennedy Jr., calling his views an "embarrassment."
The 2026 Congressional Run: A New Kind of Kennedy
In November 2025, Jack officially stopped being just a "political correspondent" for Vogue and started being a candidate. He’s running for New York’s 12th Congressional District, the seat being vacated by Jerry Nadler.
This is where the rubber meets the road.
Can a guy who trolled the internet by claiming he had a son with Usha Vance—a joke that left some people confused and others annoyed—actually win a seat in the U.S. House of Representatives? His mother, Caroline, seems to think so. She’s gone on record saying she’s "impressed" by how he uses social media to highlight Democratic weaknesses.
It's a gamble. Most old-school voters see a Kennedy and expect a certain level of "solemnity." Jack gives them skits. He’s betting that the 2026 electorate doesn't want another polished statue; they want someone who feels real, even if "real" means being a little bit of a troll.
Facing the Family Ghosts
It hasn't all been paddleboarding and jokes, though. The last year has been brutal for the Schlossbergs. The death of Jack’s sister, Tatiana, in December 2025 hit the family hard. She was the quiet one, the environmental journalist who stayed out of the fray. Her passing at just 35 years old was a grim reminder of the "Kennedy Curse" narrative that the media loves to trot out every few years.
Jack handled it in his own way—posting quotes from Lincoln and Frost, mixed with his sister’s own words. It was a rare moment where the "silly goose" persona dropped, and people saw the man who served as a ring bearer at JFK Jr.’s wedding when he was only three years old. He does remember his uncle. He remembers the Pontiac convertible and the way John used to call him "Jackolatern."
That’s why he went after Ryan Murphy so hard in 2025. When Murphy produced American Love Story about JFK Jr. and Carolyn Bessette, Jack called it "grotesque." He isn't just protecting a brand; he's protecting a family that has already given enough to the public's imagination.
What Most People Get Wrong
The biggest misconception is that Jack is "trying" to be JFK Jr.
He’s not. He’s actually doing the opposite. By being loud, weird, and hyper-visible on his own terms, he’s killing the myth of the "silent, tragic Kennedy." He’s making the dynasty accessible.
Is it working? The polls for the 12th District will tell us eventually. But for now, he has 1.7 million followers who aren't just there for the history lessons. They’re there for the chaos.
How to Follow the 2026 Race
If you’re looking to see how the "Jack Schlossberg JFK Jr." dynamic plays out in real-time, watch his campaign stops in Manhattan. You’ll see the older generation looking for the uncle, and the younger generation holding up phones for a selfie with the TikTok guy.
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Next Steps for the Curious:
- Check the Primary Schedule: The Democratic primary in New York is the real hurdle. Watch how Jack handles debates against "serious" policy wonks.
- Monitor the Socials: If he starts getting "boring" and professional, it might mean his consultants have finally won. If he keeps posting weird videos, he's still running his own race.
- Read the Vogue Archive: His 2024 columns give a surprisingly deep look at his actual policy stances beyond the memes.
Jack Schlossberg isn't the return of JFK Jr. He’s the first version of himself. And in 2026, that might be exactly what the Kennedy legacy needs to stay relevant.