Monday, June 1, 2026

Hit the Road, Jack: Kennedy Grandson Posts New Video, Prompts Comparisons to Famed Eccentric Ancestor

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Caroline Kennedy’s son, Jack Schlossberg, won’t stop posting strange videos.

In the new one, Jack — grandson of John F. Kennedy — plays a character named Reginald, who sings Joe Biden’s praises with an English accent.

Add Reggie to a list of characters with various accents whom Schlossberg plays in these videos. They are all pro-Biden and anti-Trump and cousin Robert Kennedy Jr. If they were set up in a professional manner, they might be effective. But Schlossberg is coming off now like a clown.

Most comments on the videos suggest these things: that he’s as mentally unwell as his grandmother, Jackie’s, famously eccentric cousin Little Edie Beale, of “Grey Gardens”; that his continued videos from a beach setting suggest he has no actual job and is out of touch with reality.

All of this points to Schlossberg actually maybe doing Biden hard, not good. He clearly knows his facts about Biden’s accomplishments. But to keep presenting them in a cavalier way is just tempting ridicule. One commenter said: “The ambassador [Caroline is US Ambassador to Australia] must be embarrassed with these undignified and embarrassing posts. Put a suit and tie on Sir.”

Another said: “Caroline Kennedy – get him into rehab.”

Comparisons to Edie Beale are not favorable. In the legendary Maysles brothers documentary, the Beales mother and daughter — Jackie Kennedy’s cousins — are living in a rundown Hamptons mansion called Grey Gardens. Little Edie’s famous line is “I’m a staunch person.” Now TikTokers are using that meme in videos covering Schlossberg’s postings. It’s not a good look.

Whatever is going on, maybe someone close to Schlossberg can put and end to it. Maybe that person would be the girl in the bikini who seems to be filming the videos. Her reflection turns up in one of them. He’s definitely JFK’s grandson.

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Roger Friedman
Roger Friedmanhttps://www.showbiz411.com
Roger Friedman is the founder and editor-in-chief of Showbiz411. He wrote the FOX411 column on FoxNews.com from 1999 to 2009 and previously edited Fame magazine and wrote the "Intelligencer" column at New York 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. is articles have appeared in dozens of publications over the years including New York Magazine, where he wrote the Intelligencer column in the mid 90s and covered the OJ Simpson trial, and Fox News (when it wasn't so crazy) where he covered Michael Jackson. 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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