JFK’s Grandson Jack Schlossberg Loves Posting Weird, Charming Videos Online

Caroline Kennedy’s son has a unique relationship with the Internet, but it’s not entirely clear what his motivation is

ack Schlossberg speaks at the John F. Kennedy Library at the annual JFK Profile in Courage Award on May 20, 2018 in Boston, Massachusetts
ack Schlossberg speaks at the John F. Kennedy Library at the annual JFK Profile in Courage Award on May 20, 2018 in Boston, Massachusetts (RYAN MCBRIDE/AFP via Getty Images)

After seemingly taking a few weeks off, JFK’s grandson Jack Schlossberg has offered yet another bizarre video online.

In his most recent video shared on Saturday, the son of U.S. Ambassador to Australia Caroline Kennedy and her husband designer and author Edwin Schlossberg is singing “New York, New York” while walking inside a building in New York.

On Thursday, Schlossberg shared a video of himself holding up a notepad with the word “ibuprofen” written across it in capital letters. “What is this?” he asked. “What is that word? What is that? I don’t know what to do with this. What’s this?”

“What’s this, what is this?” he asked as he turned to a second page with the word “Telluride” scrawled across it. “What do you do with this? What am I supposed to do with this?”

The video was posted a day after Schlossberg posted a video that celebrated the winner of the 2024 John F. Kennedy Profiles in Courage Award, Kentucky’s Secretary of State Michael G. Adams. The video was more in line with political content that Schlossberg — who has been critical of his cousin Robert F. Kennedy Jr. and an outspoken supporter of President Biden — has posted in the past.

The pattern — a video featuring a skateboarding Schlossberg quoting “She Walks in Beauty” by Lord Byron is preceded by another political video that features him literally buttoned-up and ready to work — has played out over several weeks. On May 22, Schlossberg admitted his “hottest take” is that he doesn’t like Italian food, which was followed by another video of him moonwalking in socks in a Walmart.

The videos are all entertaining and certainly unexpected from a member of the family that many consider to be America’s version of royalty, but their existence begs the question: why is Schlossberg doing this in the first place?

The answer, wrote Slate’s Heather Schwedel in late May, might just be that Schlossberg is a lot weirder than most of us would have assumed. Schwedel recalled Schlossberg’s viral July 4, 2023, video in which he derided restaurants (“My friends don’t like eating dinner. Most people in the world don’t spend their lives eating dinner,” he said) and noted that “it more made me consider the irony that Schlossberg is so opposed to the RFK Jr. campaign when the two sometimes seem like different sides of the same unhinged coin.”

Schlossberg’s social media accounts, she continued, sometimes inspire the same concern that Schwedel expressed about that of Britney Spears: “I want to let him be, I don’t want to be glib, but, um … we’re all seeing this, right?”

Considering the effort that most of the Kennedys appear to exert to live as under the radar as they can, the fervor with which Schlossberg has embraced weirdo Internet fame could be startling. After all, despite the decades that have transpired since JFK’s presidency and even since the whirlwind that accompanied the too-short life of his son, the Kennedy family is still regarded by most Americans as almost not human … but not in this way.

The most compelling part of Schlossberg’s social media presence might be that despite it all, he seems to be filming and sharing these videos for one person: himself.

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