I Went to a Jack Schlossberg Event. I Can’t Believe I’m Saying This: He Should Win.

Politics

Just Let Him Have This

I walked into a Jack Schlossberg campaign event as a skeptic. That’s not quite how I left.

By

Scaachi Koul

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June 18, 2026 12:57 PM

Brian Snyder/Reuters

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Political events often have the tone and tenor of an exciting timeshare opportunity. Walk into one such event and you are perpetually being sold on a single, perhaps foolhardy decision that could change at least the next few years of your life. And what are you buying, exactly? The promise of hope, usually left unfulfilled. Before you know it, it’s your summer vacation and you’re stuck with an investment that you don’t necessarily believe in anymore.

A candidate like Jack Schlossberg, now running for Congress in Manhattan’s 12 th District, is at least more self-aware of his role as salesperson than most. New York 12 is an area of midtown that covers some of the richest parts of the city: Chelsea, the Upper West and Upper East sides, the Met, and the entirety of Central Park. It’s a district for and by affluent, mostly white New Yorkers, which makes Schlossberg a culturally apropos candidate. His mother is Caroline Kennedy, his grandfather is John F. Kennedy, and his cousin is, of course, snake-wrangling Robert F. Kennedy Jr. What he’s gathered from his family history is that to win an election, you have to put on a good show.

Much like his uncle John-John, however, he’s woefully ill-equipped for a job in politics. Though highly educated with a Harvard MBA and law degree, well traveled, and in the possession of an excellent hairline and strong, Kennedyesque jaw, Schlossberg is just 33 years old, has no previous experience in elected office, and is connected to political life solely through his abundantly complicated family lore. He’s perhaps better recognized for shitposting than for knowing what to do in Congress; his prolific social media posts in which he rants to camera shirtless have served mostly as a lively distraction. Maybe, if he does it right, he could distract his way into some votes.

Last Friday, Schlossberg held a rally at Manhattan’s Terminal 5, the city’s worst music venue, known primarily as a place to barf while electronic music plays on the dance floor. Amid rumors that his campaign has been disorganized with high turnover , hundreds of district residents (and a lot of Columbia students enticed by the promise of free food, which did not materialize) took shelter from a sudden thunderstorm to hear Schlossberg talk the talk. Over an hour, the candidate’s campaign brought out housing activists, union representatives, and David Letterman, whom Schlossberg has known since he was 16. The message was clear, if flawed: Vote for Jack, because the other guys are worse, and, hey, it would certainly upset Republicans. “If we won this election, I would be so happy,” Schlossberg said onstage. “But also, the people who hate all of you are going to be so mad.” He’s probably right about that much—if Republicans already resent the Manhattan elite liberal, being represented by a sloppy Kennedy would indeed be a masterful troll.

The Democrats have been using this kind of playbook for a while now: Vote for me, because the other guy sucks harder . It hasn’t worked—this strategy wasn’t helping Joe Biden when he was in the race against Donald Trump, nor did it help Kamala Harris. For a progressive candidate like Zohran Mamdani to beat Andrew Cuomo for mayor last fall, his campaign had to be the most clever, the most viral, the most linguistically careful, and the poppiest; Cuomo’s suckitude wasn’t enough on its own.*

Running against Schlossberg for the Democrats is a cornucopia of the status quo: George Conway of the Lincoln Project (and Kellyanne’s ex-husband); Micah Lasher, who formerly worked for Kathy Hochul’s New York state government; and Alex Bores, who used to work at Palantir , so I feel pretty justified in saying he sucks . It’s a sea of nightmares in suits, and among them is Schlossberg, the Dennis the Menace we don’t deserve, don’t really want, but are burdened with regardless.

And you know what? Sure. Why not. Let him win. It’s Congress. How much can he even do?

There are parts of Schlossberg’s campaign that look and sound like a typical one. His slogan, “Believe in Something Again,” is marked by an unearned optimism for the future and a conviction that we can fix everything made broken in the past decade (or more) of politics as usual. Constituents were writing out posters in support of Schlossberg: Believe in Love Again , Believe in Equity Again , Believe in the Power of Truly Representative Government Again . Much of the crowd was in their 60s, 70s, and 80…