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Jack Schlossberg’s ChatGPT candidacy – UnHerd

We live in Nepo Baby America. Bronny James is playing for the Lakers despite the inconvenient detail that he still can’t shoot a basketball. Hollywood is being run by the children of Hollywood, with half its current “It Girls” appearing as reboots of their 1980s-era actor parents — Margaret Qualley, Lily-Rose Depp, Dakota Johnson, and so on. The charts, the runways, the influencer economy, and even the news media are now populated with the failsons and faildaughters of celebrities, executives, and political VIPs. And in politics — the one place where legitimacy is theoretically supposed to flow from ordinary people — another dynastic heir pops up to audition for public office every few years. 

Enter Jack Schlossberg, JFK’s grandson, and the latest contestant in America’s longest-running reality program, So You Think You Can Kennedy?. Last week’s reports that he’s launching a bid in New York’s 12th District for the congressional seat being vacated by Rep. Jerry Nadler came packaged with Jack’s solemn Instagram videos in which he speaks like a man auditioning to play a politician in an Aaron Sorkin political drama. 

His campaign site and imagery steal valor from his famous family on the sly. Instead of using his own first name, the 32-year-old — born John Bouvier Kennedy Schlossberg — has rebranded himself simply as “Jack,” the nickname he shares with his grandfather. “Let’s Back Jack,” a slogan used to elect JFK in 1960, has been resurrected, and photos mirror famous Kennedy family portraits. One shot of Schlossberg backlit against a wall of US and New York flags mimics a photo of a 29-year-old JFK running for Congress; another, Jack in a suit on a bicycle, is a clear tribute to his more talented uncle, George magazine founder John F. Kennedy Jr.

Like the Kardashians, Schlossberg is famous for being famous (1.7 million followers and counting across X, Instagram, and TikTok). Unlike the Kardashians, he hasn’t converted that inherited fame into anything resembling work. His chief accomplishment, as Sydney Sweeney might put it, is having good genes — and cultivating the soft-focus persona of a Kennedy heir who looks like he’s contemplating the fate of democracy while actually contemplating his paddleboard stance.

The Kennedy clan was far from perfect, but it once supplied the Democratic Party with gravitas: war heroes, World War II veterans, civil-rights champions, defenders of people with disabilities, senators who spent decades in the trenches of actual governance. But every dynasty has a half-life, and the Camelot isotope is visibly decaying: Schlossberg has lived like the world’s most insufferable White Lotus character.

Born the only grandson of JFK through his daughter Caroline Kennedy’s marriage to Edwin Schlossberg, he has inherited the Kennedy hair, the Kennedy cheekbones, and the Kennedy compulsion to speak in inspirational bromides. What he has not inherited is the Kennedy capacity for actual work. Schlossberg has got the trappings of inherited wealth and power: the Yale history degree; the Harvard dual professional degree in law and business administration; and a professional résumé so thin you could slide it under a door.

He hasn’t done much beyond a few internships, a yearlong stint in Japan working for Suntory (the distillery immortalized by Bill Murray in Lost in Translation), and — yes — a gig in a surf shop in Hawaii. Schlossberg even briefly tried his hand at acting, his lone on-screen role being a cameo on a TV drama, a moment so on-the-nose it reads like accidental satire: a literal blue blood appearing on CBS’s Blue Bloods.

His most notable job to date was as a “political correspondent” covering the 2024 election for Vogue that resulted in a handful of barely-there columns offering such insights as: “I still think, at the end of the day, voting for Democrats is going to be the right way to go.” He doesn’t smoke or drink and has avoided scandal, making him a kind of Boy Scout version of Hunter Biden, minus the gritty charisma, tragedy, or actual life experience.

Schlossberg’s most developed political skill appears to be shitposting — and even that he does poorly and awkwardly. ​​When his cousin RFK Jr. decided to enter the 2024 presidential race as an independent, Schlossberg deemed it an “embarrassment” and a “vanity project,” a line that certainly has not aged well.

There was also the moment he tweeted, “True or false: Usha Vance is way hotter than Jackie O,” subjecting his own grandmother to a bizarre hot-or-not bracket. He also once claimed that he was “having a son !! Out of wedlock, yes. But we might get married,” and attached a photoshopped image of his face on a baby in Usha’s arms.

Who can forget the time he posted a childhood photo of himself naked and mid-stream on a balcony (“TFW you boycott the Met Gala”), and shared breakup thirst traps in which he opined, “Heartbreak sucks … you feel like you’re mourning someone who’s alive.” It’s not clever trolling, not meta-ironic commentary, just the kind of low-effort online flailing that makes Gavin Newsom’s smarmy troll persona look like high art.

“He’s 32 years old but hasn’t done much beyond a few internships.”

And yet Schlossberg has still somehow become a manic-pixie-dream guy for a particular kind of liberal wine mom or Trump-hating gay man. After watching a TikTok of Jack singing along to a Rihanna song, a thirsty Daily Beast editorial breathlessly claimed Schlossberg is “peak male form; Michelangelo’s David, reborn for the modern age and pounding his chest to an underrated EDM-pop tune.” But the nice thing about Renaissance art is that it doesn’t speak. Schlossberg does, and he says things like “I’m a silly goose — a silly goose who’s trying, just trying, to get the truth out there.”

The seat he’s eyeing spans Manhattan’s Upper West Side, Upper East Side, Midtown and Chelsea — one of the richest, bluest, and most densely populated congressional districts in the country (median income: around $150,000). It also faces familiar Big Apple hurdles: soaring housing costs, crumbling subway infrastructure, worsening inequality, and a growing disconnect between the ordinary New Yorker’s daily struggles and the rhetoric from most politicians — which is what fellow Millennial politician Zohran Mamdani seized on in his recent mayoral upset. 

Schlossberg is no Mamdani. He simply delivers meaningless lines such as, “With control of Congress, there’s nothing we can’t do.” But what does he want to do exactly? He doesn’t say exactly. His “12 for 12” campaign platform offers 12 vague “promises to the people of the 12th District” that read like a Kennedy Center gift-shop calendar. (“Politics isn’t about winning points in a debate — I’m running for Congress because I want to legislate.”)

The fantasy of an empty-calorie Kennedy running for Congress emerges from a broader Democratic delusion: that the best way to counter Trump’s celebrity politics is with celebrity candidates of their own. Over the years, the party has floated Matthew McConaughey, The Rock, Oprah, Mark Cuban, even Stephen A. Smith. And while those flirtations with running for president were treated as only mildly absurd, it remains true that compared to Jack Schlossberg, Stephen A. Smith looks like Stephen A. Douglas.

Yet Schlossberg insists that this political theory is what matters most. In a Sept. 17 Instagram post, he unveiled his “theory of change”: since Trump is a “media presidency,” Democrats need a “media resistance strategy.” As he put it: “Democrats need a show people want to watch.”

The problem is that he is not that show. He is the show people mute midway through but leave playing in another tab, so it doesn’t autoplay something worse. Voters should be clear-eyed: the medium is still the message. JFK was the first great TV politician; Jack Schlossberg is what that lineage has dwindled into — the first Kennedy engineered for the algorithm age. He looks and sounds the part, but everything else feels like a ChatGPT hallucination of a candidate. It’s time that voters touch grass instead.


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