What’s the Deal With Jack Schlossberg? (2024)

gone viral June 27, 2024

By Danya Issawi, a fashion news writer at the Cut. She previously worked across the newsroom at the New York Times, including on the “Style” desk and the Pulitzer Prize-winning COVID-tracking team.

What’s the Deal With Jack Schlossberg? (2)

Photo: Karwai Tang/WireImage

Jack Schlossberg’s social-media posts are a gold mine of entertainment. Maybe you’ve come across some of them — like the video of him singing, a bit off-key, “Ticket to Ride” by the Beatles while dancing around shirtless, or him strutting around in tight biker shorts to an AC/DC song? Or maybe a video or two of him mimicking a British accent? Maybe you’ve even discovered he’s a Kennedy — but what’s his deal? Let’s get into it.

@jack.schlossberg
She walks in beauty by Lord Byron
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Just who is Jack Schlossberg?

Jack Schlossberg’s full name is John Bouvier Kennedy Schlossberg. Yes, those Bouviers, and, yes, those Kennedys. He’s the son of Caroline Kennedy and Edwin Schlossberg, and the only grandson of President John F. Kennedy. It’s unclear what the 31-year-old does for work,but after graduating from Yale, Harvard Law School, and Harvard Business School, Schlossberg passed the bar exam.At the moment, his main occupation appears to be sh*t-posting across social-media platforms, and after years of doing so, the internet is taking notice.

Why is everyone talking about Schlossberg’s social-media presence?

Well, because it’s chaotic. It’s raw. His Instagram presence appears to be one part diplomacy and two parts wacky. Last month, he posted six videos in a row, ranging from those speaking as his alter ego, Reginald Covington, about Bidenomics (he called the president a “powerhouse”) to singing Frank Sinatra’s “My Way” at the top of his lungs while driving. Another recent video features him prim and proper in a crisp button-down, congratulating an honoree on behalf of the renowned JFK Library, followed by a post of him dancing to Michael Jackson in Walmart, moonwalking in socks and no shoes. His tweets oscillate between posts like “Pence and congressional Republicans have also failed the test of courage” and his personal thoughts on Christ’s body type (“Jesus was thin. Toned, but not big.”) Ah, the duality of man. A comment on the latter video read: “I pray to god the government never takes you away from us.”

Schlossberg launched his Twitter account in 2014, and his posts have been quirky from the beginning. And it seems like he really committed to the bit in the past year. As a result, Gen-Zers and some young millennials have become taken with him and his content, garnering him nearly 159,000 followers on Instagram. Sure, he’s got the Kennedy good looks (thick head of hair, nice smile, physique of someone who clearly grew up playing water sports near a beach, etc.), but it’s his attempt at levity that truly draws his audience in.

Sure, stiffer people might not get Schlossberg’s humor or approach.

Recently, several articles have emerged questioning what Schlossberg’s deal is. “Is he crazy? Or just a fox?” I’m no psychiatrist, so I can’t speak to his mental health, but what I can say is that I think Schlossberg’s zany, unpredictable, and borderline incoherent sense of humor is exactly the kind prevalent on youth-dominated apps like TikTok.

And although it might seem nonsensical, he actually is trying to get a message across. He’s made clear his public support for President Joe Biden, and on multiple occasions engaged in blatant mockery of his relative and presidential candidate Robert F. Kennedy Jr. (“I have no idea why anyone thinks he should be president. What I do know is that his candidacy is an embarrassment,” Schlossberg said of RFK Jr., whose own siblings publicly denounced his decision to run). He recently wrote a guide for Vogue outlining his thoughts about Thursday’s debate, noting that he’s “most interested in how Trump answers questions about the 2020 election” and “eager to see if his sense of humor is still there.” And when it comes to Biden, Schlossberg wants “to see how the president handles inflation.”

It’s no secret that Gen Z isn’t a fan of Biden. But through his online persona, Schlossberg chips away at the image of perfection, (yes, parsed with tragedy) projected onto the Kennedy family by publicly speaking against RFK Jr. and instead uses his platform to cast all his wacky characters and one-liners toward convincing his followers to vote for Biden: “First things first, no economy on earth is growing as fast as the United States under President Biden,” Schlossberg said in a video, assuming the exaggerated British character of Reginald. “If you think the Europeans wouldn’t kill for those numbers …”

One family friend told Town & Country, “He’s a good kid, but I do not understand what he’s doing. I watched a little. People sent it to me. I have no f*cking idea … People do really stupid sh*t, and they do it when you think they’re too smart to do it.” Another worried about the optics of a wealthy heir performing “working-class” accents. Schlossberg, though, doesn’t quite care: “I think a lot of people are confused,” he told the outlet. “But I think a lot of people understand what I’m doing.”

Why do people call Schlossberg “Little Edie”?

Often, fans of Schlossberg draw parallels between him and another of his relatives: Edith Bouvier Beale, his grandmother’s cousin. Why? He’s got whimsy. He’s got joie de vivre. He’s got that nonlinear, untraceable line of thought that makes so little sense that it actually makes sense. They leave comments on his more “whimsical” videos, like “welcome back Little Edie” and “little edie is strong in this one.” A former socialite, Little Edie and her mother’s life in a dilapidated and unkempt home in the Hamptons was dissected in a 1972 New York Magazine story and a subsequent documentary titled Grey Gardens. The film, even 50 years after its release, has become something of a cult classic generation after generation, in part because of Little Edie’s quirky way of being (she performed several dance numbers for the filmmakers while also caring for her ailing mother); her frankly iconic way of dressing (always with a headscarf, nearly never missing a brooch); and her prolific one-liners (“But you see in dealing with me, the relatives didn’t know that they were dealing with a staunch character, and I tell you, if there’s anything worse than dealing with a staunch woman … S-T-A-U-N-C-H.”) It’s that latter trait that seems to run strong through Schlossberg’s way of being, too.

So, am I supposed to take Schlossberg seriously?

If you want to, sure. So what if the future of the Kennedy dynasty likes to dance around topless or in little shorts? At the very least, Schlossberg has mildly swayed the youth to feel something, even if it’s simply invoking the conviction to only use pens on special occasions (pencils for everything else) and doing away with massage guns. That’s more than any serious, well-to-do politician or nepo baby has done in quite some time.