Jack Schlossberg: America’s vanity heir

The Kennedy dynasty has spawned its most hollow iteration yet.

The blessing of being a Kennedy (no relation) is that you are born with the capacity to do whatever you want, with no barriers to success; to be admired for no reason besides your beauty and charm. The curse of being a Kennedy is that your baser instincts are stronger than the average bear’s. JFK and RFK Sr chose what politicians self-congratulatorily call lives of “public service”, which for the former was pretty cushy – “if I don’t have a woman every three days or so I get a terrible headache,” the late president once reportedly said. Many settle for mere Senate seats, or perhaps appointments to the ambassadorship of Japan, like Caroline Kennedy before her current post in Australia. It’s very nice to be called “your excellency”, I’m sure. There are looming threats across the world but America’s real goal, for some reason, is to sufficiently flatter this one messy family, which is made up of not just nepo babies, but a whole nepo family tree with a complex nepo root system.

What Kennedys choose to do can tell us a lot about America, culturally. In fact, whatever you find a Kennedy doing is what everyone would do if they could, and if they were not of particularly high character, and if they were probably drunk. These are just the rules of the American Kennedydom. Don’t ask who made them or why or if they are fair, I simply report. If you’re a Kennedy and you want to be an anti-vaxxer, “environmental activist”, an alleged womaniser, or if you want to kill a bear and drag its decaying carcass through Central Park to dump it there, you will probably be very successful, as RFK Jr is. Or look at half a dozen other manqués from the same clan: if you would rather skate into Yale (should Harvard fail to woo you), you may. If you want to have a career in policy and politics, you can have your pick of law schools, and you’ll be a senator by the time you can write into the New York Times arguing, against available evidence, that historians say your grandfather would have avoided going into Vietnam.

The last example brings us to the public face of the latest generation of Kennedys, Jack Schlossberg, son of Caroline. Recently named as Vogue magazine’s political correspondent, Schlossberg has made a name for himself as… just kidding. His name was made already. But he has used his name – which changes from Kennedy Schlossberg to Schlossberg, depending on the setting – differently to how his parents and grandparents and aunts and uncles traditionally have. Today, given the privilege of good looks, money and fated success at whatever you choose, the thing someone would choose is TikToking and being a journalist. The king of Camelot today is he who posts.

Schlossberg’s columns and “political reportage” are not exactly thought provoking. They don’t need to be and Schlossberg knows it. All he has to do is share his musings, such as what he once dreamed about and a few mentions of “my grandad” to his 400k TikTok followers with his shirt off and he’s worth double whatever salary Vogue pays him. As a self-described “silly goose”, Schlossberg knows that despite being a 31-year-old man spending his days posting TikTok videos of him impersonating different American voting demographics and breaking coconuts and dancing wildly, his petulance won’t hinder his political prospects but help them. In the same way that Kamala Harris knows that a few mentions of “brat summer” and a decent pair of trainers will keep the vibes so immaculate that she won’t be required to tell anybody her policy positions on things like the economy, foreign policy or immigration.

So what does Schlossberg really believe? If his social media is anything to go by, he believes that Miele vacuum cleaners are superior to Dysons; he wonders if AI is sexual; he thinks that there is “Soooo much SALAD in Washington DC no?”. After appearing seemingly out of nowhere earlier this year, Jack seems to have perfected his bits, and has even incorporated different characters. There’s a Russian named “Vlad” who believes Bobby Kennedy Jr’s run is good for Vladimir Putin. There’s Joshua, an old Jewish man from New York, who doesn’t get why anyone would vote for Bobby Kennedy Jr. Then there’s Wade, a Southerner with daughters who doesn’t want them growing up with President Trump. And lastly there is the Bostonian Jimmy, who believes that “Joe Biden’s economic record is second to none”. Why does he do this? When asked, he said in an interview, “I can’t sing and I can’t dance, but I can do accents and I’ve always been able to,” adding, “I think it’s up to all of us to try to do what we can… and this year, for me, that meant making these videos online.”

It is entirely possible, and even likely, that Schlossberg’s viral videos will kickstart his political career and he will soon be an influential voice in American politics. Will his TikTok videos harm this? In one video Jack asks himself if he “really wants to do this” because he’s “playing with fire”. His answer is that yes, he does. And why wouldn’t he? He’s a Kennedy after all.