Jack Schlossberg (Michael Loccisano/Getty Images for Empire State Realty Trust)
Jack Schlossberg, the only grandson of former president John F. Kennedy and now a Democratic candidate for New York’s 12th Congressional District, disclosed millions of dollars in assets held in four trust funds—but no “earned income,” financial records reviewed by the Washington Free Beacon show.
Schlossberg, according to the filings, didn’t actually work a job last year but holds between $10.5 million and $31.9 million in assets parked mostly in four trust funds and four JPMorgan accounts. Must be nice. One of the trusts includes a stake of as much as $5 million in Red Gate Farm LLC, the entity that manages the remaining 60 acres of Jacqueline Kennedy Onassis’s sprawling Martha’s Vineyard estate (the Kennedy family has netted $37 million selling 336 acres of the property). Schlossberg revealed a more modest stake in Rory’s Place, an “eatery featuring wood-fired fare” owned by his sister’s wife. It has garnered reviews like, “I ordered 6 oysters, and one of them didn’t have an oyster.”
Schlossberg may not have had a job but he had plenty of income. In 2025 alone, he made up to $1 million in dividends and capital gains from an investment in chipmaker Nvidia. He also disclosed a number of “positions,” people like Schlossberg might call them jobs, including one as the “managing member” of Squid Island LLC, a “social media commentary” company worth up to $100,000. It generated no income. While he said he was a “political correspondent” for Vogue, the magazine said he didn’t hold the position in 2025 or 2026, the time period the disclosure covers.
“The disclosures tell the story of a 33-year-old loaded with family money who does little besides posting online,” our Jon Levine writes. “Schlossberg has amassed hundreds of thousands of followers on Instagram and TikTok, where he posts bizarre political content. In one since-deleted video, Schlossberg filmed himself performing a Nazi salute that was likely intended to mock Tesla billionaire Elon Musk, the Free Beacon reported. … Schlossberg, who holds degrees from Harvard and Yale universities, briefly worked as a staff assistant in the State Department’s Bureau of Oceans in 2016. His longest-running position appears to be his role as chairman of the New Frontier Award at the John F. Kennedy Library Foundation, which he held from 2013 to 2023.”
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