The Kennedy myth never dies — it just gets weirder

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At first glance Jack Schlossberg seems like your average Ivy League lunkhead. Tall and handsome, his lanky six-foot-two frame has rangy athleticism, he boasts a thatch of hair that geneticists should task with study and he can always bust a camera-ready, doe-eyed, heartbreaker grin. He’s urban, he’s part of the liberal cognoscenti; he skates about the parks like a real New Yorker in his singlet, cap set backwards with its peak against his nape. 

Take a closer look, however, and you start to see the resemblance: the chiselled cheekbones, the glowering brow. He has all the hallmarks of his ancestral bloodline. Jack Schlossberg is unmistakably a Kennedy.

John “Jack” Bouvier Kennedy Schlossberg was born in 1993, the youngest child of Caroline Kennedy and designer and artist Edwin Schlossberg. He is named after his maternal grandfather, the 35th US president John F Kennedy. Ted Kennedy was his godfather and great uncle. He bears an uncanny likeness to his uncle, John F Kennedy Jr, the attorney, socialite and publisher who died in 1999. Schlossberg was a ring bearer at JFK Jr’s wedding, and shares the same proclivity for writing and wearing not too many clothes.

Schlossberg has degrees from Yale and Harvard in history, law and business administration, briefly worked in the Bureau of Oceans and International Environmental and Scientific Affairs and has turned his hand to journalism. He’s written for the Washington Post, New York magazine and People but his chief achievement since graduation has been creating content and cultivating his social media presence with a slew of TikTok films. Some half a million followers now tune in regularly to watch him singing ditties from behind the steering wheel, cogitating on the park run, providing “hot takes” about Big Tech and, increasingly, “memeing for democracy”.

Some observers might find Schlossberg a bit peculiar, his goofy brand of humour comes across as slightly odd. Watching him crooning feels like being on a Tinder date that you’d like to exit. And I think it’s a red flag he doesn’t like to shower, wash his hair or brush his teeth. But in spite of this, or perhaps because of it, the 31-year-old has been adopted to help explain politics to the young and disaffected. US Vogue signed him up as a political correspondent in July, while Kamala HQ has been using him as an interlocutor to get the vote out and energise Gen Z. 

His content is now pivoting away from moochy explainer videos to find him chatting deep dish pizza and policy with Josh Shapiro, the governor of Pennsylvania, hanging out with swing-state senators and doing porch-side interviews with major figures in the Democrat community. His access is formidable: most Democratic elders seem to treat him as you might a hyperactive nephew — an inevitable fixture whom you are fond of but sometimes wish would go away. Schlossberg carries with him the golden privilege of being a Kennedy. He may be a smelly skater-boi crossed with a puppy, but he’s still a scion of the mythic Camelot. He got the chance to remind everybody of that connection at the Democratic National Conference, in Chicago, during which he gave a two-minute speech. He told the assembly why his grandfather was his “hero”: because “he inspired a new generation to ask what they could do for our country. Today, JFK’s call to action is now ours.” 

Schlossberg may lead with a unique brand of “silly goose”, but of the current crop of Kennedys he’s probably the sane one. Few things are stranger than the spectacle of his cousin Robert F Kennedy Jr’s late career in politics: the now retired presidential candidate and Trump supporter revealed this week he is being investigated for collecting a whale specimen 20 years ago: he cut its head off with a chainsaw and then bungee-roped it to the family car. Following the brain worm, and the story of the dead bear cub (he planned to skin it but then dumped it in Central Park, you remember?), and an allegation of sexual assault (over which he apologised without admitting guilt), RFK Jr’s reputation for being a bit zany has now been reclassified as dangerously mad. 

Jackie Kennedy may have coined the expression Camelot to help mythologise her late husband’s presidency, but the myth gets ever stranger and more powerful by the year. One wonders whether a Kennedy can ever be an ordinary mortal or must always cultivate an outsize personality to live up to their famous name. Schlossberg is harnessing more statesmanlike authority while cruising on his hunky affability and adjacent fame. His schtick can feel as though it has been cynically workshopped to “play” with next gen voters, but at other times his uncensored edits seem spectacularly untamed. 

As a representative of Camelot 2.0 he ticks all the boxes. He’s politically aspirational, charming, non-confrontational and looks cute in a suit and in running shorts. For a voting sector that has been put off by the relentless negativity of recent politics, Schlossberg is the perfect spokesman: he sandwiches his easy-peasy calls to action — “vote blue” (hell, you don’t even need to know the names on the ballot), “reproductive freedom”, “don’t cry, vote!” — and then gets back to the stuff of life, like moonwalking in the supermarkets in his filthy dirty socks.

And, yes, he isn’t hugely funny, or even amusing, but he’s got that rare ancestral glow. Camelot 2.0 is the same but different and while our collective weakness for Kennedy connections might smooth his transition into more serious politics, as with so many of his brethren it’s hard to work out where the focus starts and the charisma ends.  

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