Jack Schlossberg, the only grandson of former president John F. Kennedy who is running in the Democratic primary for New York's 12th Congressional District, received no "earned income" in 2025 but holds millions of dollars worth of assets in four trust funds, a Washington Free Beacon review of his financial disclosures found.
The total value of Schlossberg’s disclosed assets ranges from $10.5 million to $31.9 million, according to the disclosures, which cover the period between January 2025 and February 2026. His assets include lucrative investment portfolios parked in four trust funds worth between $4.1 million and $11.7 million, the 25-page document shows. The documents indicate Schlossberg owns a stake of up to $5 million in Red Gate Farm LLC, the corporation that manages the remainder of a vast Martha's Vineyard estate once owned by his grandmother, Jacqueline Kennedy Onassis.
Schlossberg generated plenty of income from his financial holdings: He reported receiving up to $1,000,000 in dividends and capital gains from an investment in chipmaker Nvidia in 2025 alone. But he disclosed no "earned income"—that is, money earned from working a job.
Schlossberg also disclosed a number of "positions." He listed himself as the "managing member" of Squid Island LLC, a "social media political commentary" company worth up to $100,000; as a "member" of Red Gate Farm LLC, the corporation that controls the Martha's Vineyard estate; as a "member" of Rory's Place LLC, a restaurant in California; and as a "political correspondent" for Vogue. A Vogue representative, however, said Schlossberg "was Vogue's election correspondent through the 2024 election, so he did not work with us in 2025."
The disclosures tell the story of a 33-year-old loaded with family money who does little besides post commentary online. Schlossberg has amassed hundreds of thousands of followers on Instagram and TikTok, where he posts bizarre political content. In one since-deleted video, he filmed himself performing a Nazi salute that was likely intended to mock Tesla billionaire Elon Musk, the Free Beacon reported.
In addition to his short-lived stint at Vogue, Schlossberg, who holds degrees from Harvard and Yale universities, briefly worked as a staff assistant in the State Department's Bureau of Oceans and International Environmental and Scientific Affairs in 2016. His longest-running position appears to be his role as chairman of the John F. Kennedy Library Foundation’s New Frontier Award, which he held from 2013 to 2023.
Schlossberg’s congressional bid is off to a rocky start, though he sat down for a friendly interview with CNN's Dana Bash on Wednesday. His campaign manager resigned in December, just a month after the Kennedy heir declared his candidacy, and his social media antics have drawn scrutiny. In January 2025, Schlossberg posted a comment on X about procuring "Jew blood" and male semen in an apparent dig against Secretary of Health and Human Services Robert F. Kennedy Jr., his mother’s cousin.
The Kennedy family originally listed Jackie Kennedy's sprawling Martha's Vineyard estate for $65 million in 2019. Rather than sell the entire property—home to "stunningly beautiful windswept coastal dunes, wetlands, hillocks and salt-blasted heathlands," according to the Vineyard Gazette—the family sold a portion of the property spanning 336 acres to a nonprofit that planned to conserve the land. Though the family has received praise from conservationists for doing so, it received $37 million in the sales and still controls the 60 acres that contain the family home and other buildings. Schlossberg was spotted at the estate's private beach in 2021.
A focus on conservation efforts is apparent in Schlossberg’s disclosure. The Kennedy scion reported "environmental and climate" holdings worth up to $250,000. He did hedge his bets with fossil fuel positions, though, holding a stake in "Contango Oil and Gas Management" worth no more than $15,000.
Schlossberg also disclosed a stake in Rory's Place, an "eatery featuring wood-fired fare" and "a natural wine selection" in Ojai, Calif. Operated by the wife of Schlossberg's sister, Rose, the restaurant has garnered decidedly mixed reviews.
"For a relatively expensive (for how much you received) steak it was arguably the worst steak I have ever eaten," wrote one annoyed Yelp reviewer, who also noted an added "3% extra on your bill for ‘employee health’ whatever that means!"
Another Yelp reviewer wrote that "the food is inconsistent and not good, the attitude of the staff is appalling, it seems like no one is managing it at all," and warned others not to eat at the restaurant.
"I ordered 6 oysters, and one of them, didn’t have an oyster," that reviewer noted. "I told the waiter, and she told me, that’s how they come."
Though Schlossberg’s assets are mostly illiquid, he did report having no debts. A representative for Schlossberg did not respond to a request for comment.
