Sentient boat shoe runs for Congress
Jack Schlossberg, the sentient boat shoe and semi-employed TikTok user, is running for Congress in New York. It was bound to happen. The 32-year-old Democrat belongs to the Kennedy dynasty—that inexplicably beloved menagerie of goon-faced Habsburgian freaks, Nantucket douche bros, chronic alcoholics, 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 flare.
Schlossberg is undeterred by the fact that no one really wants him to run for Congress—not even his own mother. Why shouldn't he be in politics? He has a family pedigree that most mainstream journalists would consider impressive. He is the great-grandson of Joseph P. Kennedy, the notorious Nazi sympathizer. He is the sole grandson of John F. Kennedy, the famed pervert who preyed on teenage interns while serving as president of the United States. His mother, Caroline Bouvier Kennedy, is the cousin of Arnold Schwarzenegger's ex-wife. His great-uncle, former senator Ted Kennedy (D., Mass.), killed a woman with his car and sexually assaulted a waitress with former senator Chris Dodd (D., Conn.) in 1985.
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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 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. An attempted comeback was inevitable, and the media were more than happy to play along.
Schlossberg's campaign launch coincided with an exclusive softball interview on MSNBC and a lengthy New York Times profile that included a supportive quote from David Letterman, a family friend, and a vintage-style video montage designed to resemble old footage of JFK. It's worth noting that not all journalists were so obliging. "It fills me with rage that this fuckboy thinks he should be my congressman," wrote Josh Barro, a New York-based podcast host. Semafor social media director Josh Billinson noted the egregious crease lines in the American and New York flags he clearly "just ordered off Amazon before the campaign photo shoot."
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The Kennedy scion is running to succeed the outgoing Rep. Jerry Nadler (D., N.Y.), who represents the state's 12th district covering Midtown Manhattan and Central Park. Nadler's longtime aide, state assemblyman Micah Lasher, is already running in the Democratic primary. Nadler told CNN in September that he would prefer to be replaced by a candidate who, unlike Schlossberg, has actually accomplished something in life.
The evidence is overwhelming that Schlossberg should not be taken seriously as a person, much less a politician. He reportedly sleeps on a bed comprising "two massage tables covered in shark-patterned sheets that he has had since eighth grade." He has described the voluptuous Hollywood starlet Sydney Sweeney as "not hot." Although he has three degrees from Harvard and Yale, Schlossberg has very little experience when it comes to having a real job that doesn’t involve standing next to his mom. He recently worked at a surf shop in Hawaii, and wrote seven opinion columns for Vogue magazine during the 2024 election. His final contribution—"The Keys to @KamalaHQ's Viral Success"—was published two weeks before Kamala Harris lost to Donald Trump in decisive fashion.
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Schlossberg did not react well to Trump's election. He appears to have suffered a mental breakdown on social media that even the Kennedys described as an "embarrassing earthquake" of cringe content. He joked about having a baby with Usha Vance, wife of Vice President J.D. Vance, and asked his followers if Usha was "way hotter" than his grandmother, the fashion icon and preeminent cuckqueen Jackie Kennedy Onassis. Robert F. Kennedy Jr.'s daughter Kathleen said she hoped Schlossberg would "get the help he needs."
The scion's video output, both before and after the election, showcased his increasingly erratic behavior. He impersonated Melania Trump in a blonde wig, and delivered a bizarre rant about restaurants. "You have to read to get your food?" Schlossberg asked. "Why? You don’t actually need to do that, and that’s why I’m never, ever going to a restaurant again." He has repeatedly filmed himself singing and dancing without a shirt, or speaking directly to the camera using a dialect one might describe as "flamboyant homosexual." He describes himself as "very straight," but concedes that "people often wonder" about that.
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"I feel sorry for the kid," the attorney Alan Dershowitz told the Times. "He's obviously disturbed. Everybody on [Martha's] Vineyard feels sorry for him. Generally, when he’s with his mother, he’s well behaved, but then goes off on these wild rants."
Following what many presume to have been a family intervention, Schlossberg briefly stopped posting online and deleted most of his zaniest content. He soon returned and hasn't looked back. He launched a short-lived YouTube series that involved him driving around in a van ranting about Trump. He even tried to become an actor. It didn't work out, but the experience boosted his confidence. "I believed in myself as a performer," he told Times columnist Maureen Dowd. "That led me to the social media realm."
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It goes without saying that Schlossberg—or any member of the Kennedy family—can never be allowed to serve in Congress. He might be the only candidate in history who deserves to lose even more than Sean Eldridge, the obnoxious philosophy major who lost to the incumbent Republican by 30 points in 2014. Eldridge's wealthy husband, Chris Hughes, bought several mansions in multiple districts in an effort to get his spouse elected. Hughes is best known for being Mark Zuckerberg’s roommate at Harvard and inventing the Facebook "poke" button.

