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Politics & Media
Nov 20, 2025, 06:29AM

High Hopes Revisited

Jack Schlossberg was born to serve in the House of Representatives.

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It’s hard to tell if Jack Schlossberg, grandson of JFK, daughter of Caroline, is really going to enter the primary to fill septuagenarian Jerry Nadler’s 12th District Congressional seat that encompasses Midtown Manhattan, Chelsea, the United Nations and, the way gerrymandering goes, probably parts of Harlem too. It’s hard to tell because everything in politics, (at least on the East and West Coasts) is hard to tell: is this an elaborate goof, a means of turning the 75-year old legacy of The Kennedys, already a farce, upside down and restoring some humor to the increasingly strange and thought-be-petering-out “dynasty”?

I think, but won’t make an Emmanuel Clase wager on it, that The Washington Free Beacon’s purple-prose-people-eater, Andrew Stiles, was serious last week when he wrote a scabrous take-down of sort-of-young Jack (he’s 32, and still a Democrat). Judging by Stiles’ prose, maybe he and Jack ought to tour the country as a two-man show; I’m sure it’d pay better than whatever the Beacon doles out.

Stiles wrote: “Jack Schlossberg, the sentient boat shoe and semi-employed TikTok user, is running for Congress in New York. It was bound to happen. [He] belongs to the Kennedy Dynasty—that inexplicably beloved menagerie of goon-faced Habsburgian freaks, and bloated sex pests. Schlossberg, a mentally deranged internet addict who cracks jokes about guzzling ‘Jew blood’ and ‘male jizz,’ has sought to inject the storied Kennedy brand with Gen Z flair.”

After a tired litany of past Kennedy excesses—most true—including Uncle Teddy’s sexual assaults and Chappaquiddick, grandfather JFK’s bed-hopping while in the White House, great-grandfather Joe’s Nazi sympathies and implied, but not listed, all those Kennedy cousins who were up to no good at home and abroad, he slips into serious mode. He quotes Josh Barro, a Manhattan-based podcaster (I’m a podcaster, you’re a podcaster, let’s all go to the beach!): “It fills me with rage that this fuckboy thinks he should be my Congressman.” Barro was once a Republican, and is now a “reluctant” Democrat.

Why? Was the mealy-mouthed Nadler anything more than a “fuckboy”? Should Schlossberg eventually win the 12th District seat, and I hope he does, for the sake of entertainment, he’ll vote the Democratic Party line, maybe make a few outrageous speeches in Congress (accompanied by a TikTok-approved girlfriend or boyfriend, dressed in revealing garb, and liven up the joint). AOC and Zohran would be jealous, and what’s to complain about that? Sounds like a lot more fun than the 19th-century retiring relics like Chuck Schumer and Nancy Pelosi. Schlossberg (sort of) skewers Trump, but even as he remains a Democrat, would it surprise anyone if he took young Barron Trump under his wing and made joint bipartisan proclamations in Manhattan, alternating between the Carlyle Hotel and Trump Tower?

More Stiles: “The Washington Free Beacon predicted that Schlossberg would run for office back in 2020 after his cousin, former representative Joseph P. Kennedy III (D., Mass.) lost the Democratic primary for the U.S. Senate. It was a great day for America. But the Kennedy clan is full of rich weirdos with nothing better to do than exploit the media’s obsession with their dead relatives.” (Maya King, in The New York Times, wrote a perfunctory story about Jack’s run for Congress, with a few caveats about his oddities.) Stiles ought to acknowledge that Joe III (a teetotaler, like Trump) never had a whiff of scandal associated with him, aside from a presumption that he deserved a Senate seat.

Stiles is correct, however, that the media remains Kennedy-obsessed. On Nov. 11, faded flower Maureen Dowd wrote a very long profile of Schlossberg (and naturally invoked Henry IV, Falstaff and Hamlet) in the Times, which was suitably obsequious, even if she recounted some of his kinks. Schlossberg is especially vicious when addressing his cousin Bobby Kennedy, Jr. the family’s apostate for aligning with Trump. Dowd: “In an Instagram video… he said: ‘I’ve got a challenge for you. Me and you. One on one, locked in a room, we hash this out. Nobody comes out until one of us has autism. What do you say?’ In another video, since deleted, he imitated his cousin’s static-y voice, a condition of spasmodic dysphonia.”

If Crazy Jack wins next year, Democrats have little reason to worry: he’ll vote with the party every time. Maybe some of the Congressmen who still believe they’re taken seriously by the public will squirm when the entitled Millennial goes off script, but they should encourage his antics. The House of Representatives isn’t known for mirth—it’s hard to think of “characters,” aside from James Traficant, Bella Abzug, Madison Cawthorn (inadvertently) and Adam Clayton Powell—and could use some laughs. I’d like to see Bill Burr, Mollie Hemingway, Michael Moore, John Cusack, Peachy Keenan, Ben Shapiro and David Hogg win safe seats in the Lower Chamber: Americans ought to lighten up, and have a chuckle or two that these flamboyant opinionators (not that they’re all stupid) could provide.

—Follow Russ Smith on Twitter: @MUGGER2023

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