Wednesday, July 15, 2026

JFK Grandson Jack Schlossberg Continues to Unravel on Instagram: “I’m not a bad guy, I’m an honest man…I don’t like Italian food”

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It’s the continuing saga of Jack Schlossberg, determined to be weirder than his cousin, Robert Kennedy Jr.

Schlossberg, son of Caroline Kennedy and grandson of JFK, is unraveling on Instagram. Is he crazy? No. Eccentric? Yes, truly, madly, deeply. Whatever’s going on, I’m surprised his family or friends still haven’t intervened.

And what about a job? Why is he still hanging out in Hawaii, surfing and posting videos?

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Roger Friedman
Roger Friedman
Roger Friedman is the founder and editor-in-chief of Showbiz411. He wrote the FOX411 column on FoxNews.com from 1999 to 2009, where he covered Michael Jackson, and previously wrote the "Intelligencer" column at New York magazine in the mid-1990s, where he covered the O.J. Simpson trial. He also edited Fame magazine. His bylines have appeared in The New York Times, The Washington Post, the New York Daily News, the New York Post, Vogue, Details, and the Miami Herald. He is a voting member of the Critics Choice Awards (Film and Television branches), and his movie reviews are tracked by Rotten Tomatoes. With D.A. Pennebaker and Chris Hegedus, he co-produced the 2002 documentary "Only the Strong Survive," which screened at Directors' Fortnight at the Cannes Film Festival.

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