Over the past few weeks, more and more people have joined me in puzzling over a question I’ve had for a while now: What, exactly, is Jack Schlossberg’s deal?
Schlossberg is the 31-year-old son of Caroline Kennedy and grandson of President John F. Kennedy. In early May, some videos he posted on his Instagram account began going viral elsewhere on the internet. These videos are difficult to classify: In one, he breaks open a coconut. In another, he does a strange and seemingly impromptu performance of the song “Ticket to Ride.” In maybe the most discussed of the videos, he adopts multiple accents and personas to talk about politics, in particular his cousin Robert F. Kennedy Jr.’s current presidential run. (He’s against it.) In almost all of them, he is shirtless. Often, he’s being filmed by an unseen party—who is it? Could it be his mother?
I’m telling you: strange! And so were the headlines the videos inspired because, rather than properly convey their chaos, most tried to flatten the situation into more digestible narratives. In the grand tradition of it being news every time the internet discovers a new hot guy, the Daily Beast declared that “everyone” was thirsting over Schlossberg’s videos. Then we had publications like Vogue asserting that Schlossberg is “memeing for democracy.” (No.) In an oddly scoldy response, the New York Times ran a piece calling Schlossberg “un-Kennedyesque” for escalating the family feud with “cartoonish” videos.
In everyone’s defense, it’s not easy to distill what’s going on here. If I had to do it based only on the recent videos, I might say that it is my professional opinion that … Schlossberg is a big weirdo? Of course, he’s not just any weirdo but a young, handsome Kennedy weirdo, so it’s hard to look away. But the truth is that Schlossberg has been internet-famous for a while now. You may just need to have been a young American woman in the past quarter-century to fully understand.
By way of explanation, let me tell you about Josephine, whose last name I will be omitting, as a concession to her Google-ability. Josephine is 27 now, but when she was in high school, she ran a Kennedy fan Tumblr, which she was inspired to start after going to an exhibit of Jacques Lowe photos. This was also the era of Lana Del Rey’s “National Anthem” video, which traffics heavily in Camelot imagery. No wonder it all sent her down the Kennedy rabbit hole, which is not an unpopular rabbit hole to go down. In fact, Josephine is part of a proud tradition of girls who went through a Kennedy phase in adolescence. You’ve heard of horse girls, or mythology girls, or Holocaust literature girls—this is like that, but for Kennedys.
On Tumblr, Josephine was part of a small community of Kennedy girls who were Schlossberg fans. “It was mostly because he was young and hot,” she said. “The big comparison was that he looked like John-John”—John-John being the nickname for Schlossberg’s late uncle John F. Kennedy Jr. (Real Schlossberg heads know that the person he most resembles is his father, designer and artist Edwin Schlossberg.)
When Josephine first started following the younger Schlossberg, “he didn’t have a big internet persona, but I remember me and the Tumblr gang would find, like, his Yale friends on YouTube, and they made little improv videos.”
This is around when I became aware of Schlossberg too. Yeah, OK, so maybe I went through a Kennedy phase myself. Lots of girls do. Taylor Swift did. Shut up. Anyway. I remember the first time I got an inkling that Schlossberg was a different kind of Kennedy. In 2014 Gawker ran an item debunking the rumor that the then-21-year-old had come out as gay in an essay for his college newspaper. Schlossberg himself emailed Gawker, from his Yale email address, to state on the record that it was a hoax and that he wasn’t gay. Something about this made me stand up a little straighter and take notice. Schlossberg had taken swift, decisive action, and instead of going through some fearsome Kennedy publicity apparatus, he had done it himself. I recognize that this is ridiculous, but at the time, I was convinced—from his terse statement, so firm yet unhomophobic, followed by a simple “Thanks,” with a period, not an exclamation mark—that he was going to be president one day.
Did Schlossberg ask for this? For a fandom on Tumblr and a bunch of Kennedy girls being insane about him? No, not then at least. For a long time, Schlossberg did little to feed these pockets of fans on the internet, but they showed up just the same, intrigued by that Kennedy glow. Josephine recalled that for most of the time she’s kept up with him, “he was actually a boring person to follow. He wouldn’t really post much.” His enthusiasts still made fan pages for him and Redditors still speculated about his dating life, but there was sometimes little to go on. I noticed that @jacksxedits, a TikTok account that’s been posting Schlossberg fancams since at least 2020, has despite its name occasionally made forays into stanning other famous people, like Sen. Jon Ossoff and actress Roberta Colindrez, presumably during Schlossberg content droughts.
But over the past few years, it seems as if Schlossberg has started to cultivate his following a little more—or at least he’s been posting more, and posting weirder stuff. In August 2020, after he spoke at that year’s Democratic National Convention, he was praised as a shitposter par excellence by Mel magazine.
He can be funny: I find some of his tweets particularly Dadaist and incomprehensible. But I do think some of his work, such as it is, goes beyond shitposting to something else. A turning point might have come last summer, when Schlossberg went viral with a bizarre rant about restaurants: His opinion was that restaurants “ruin your whole life.” That sounds funny, and maybe it was, a little, but 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. That’s not a crime, but there have been moments when Schlossberg’s account has inspired the same feelings within me that Britney Spears’ famously erratic Instagram presence has: I want to let him be, I don’t want to be glib, but, um … we’re all seeing this, right? He himself recently mocked this very attitude in a video: “Schlossberg, dude, you’re playing with fire, man,” he says, in a dialogue with himself.
Most of Schlossberg’s family isn’t like this. “I have not really thought of the Kennedys over the last two, three decades as seeking media attention,” John Hellmann, a professor at the Ohio State University and the author of The Kennedy Obsession: The American Myth of JFK, told me. “And that just goes double for Caroline Kennedy. It all seemed to be about dignity and about not wanting to attract unwanted attention.” If other Kennedy descendants share Schlossberg’s burning desire to shitpost, they don’t do so publicly. The mystery is why Schlossberg is putting himself out there like this. When the Times called Schlossberg “un-Kennedyesque,” this no doubt is part of what the paper was snottily getting at—that while it’s OK to seek attention in running for office, starting a magazine (à la John-John), or being photographed in cool places as a socialite, doing so on social media is something to clutch one’s pearls over.
For his part, Hellmann said he understood that reaction. When he saw what Schlossberg was up to, “I couldn’t help but think, What is he thinking?” he said. In this way, the Times wasn’t totally off base to notice that something about the videos doesn’t square with the image we have of the Kennedys. “We continue to have the idea that the Kennedys are kind of like the royal family of America,” he told me. “There’s this aura about them, and we still invest them with a certain amount of hope and dreams.” Pillbox hats, wholesome family photo shoots, touch football, @jackuno flexing over a body of water: One of these things is not like the others.
Though Hellmann said he wasn’t sure to what degree this holds for younger generations of Americans, I’d say there’s still something to it—I don’t know about “hopes and dreams,” but interest and intrigue for sure. Why else would 140,000 people be following Schlossberg on Instagram? It ain’t purely for the content.
Earlier generations of Kennedys didn’t have to contend with the same media landscape we have. “The Kennedys are tied up in Americans’ ideas of themselves as a nation and as families and individuals, but it’s always connected to the media,” Hellmann said. With JFK, it was the nascent medium of television, and with JFK Jr., magazines, so why not social media? Who’s to say JFK Jr. wouldn’t have been posting Instagram stories if he were a young man today? It’s fair to say, though, he wouldn’t be doing it quite so messily. Schlossberg doesn’t merely post; he’s what GQ recently called a “chaos follow.” Hellmann told me that JFK’s “great talent was as a shaper of narrative, of story.” Schlossberg’s stories could oftentimes use some shaping.
Indeed, Schlossberg is recording the kind of weird videos that, if anything, I would associate with off-kilter reality stars. I say reality stars—i.e., people who are obsessed with attention but not necessarily talented at creating content or anything else—because TikTok stars and other internet creators tend to have a bit more savvy about these things: They are trying to build an audience, so they want to make videos people like. Schlossberg seems as if he doesn’t really care about his viewers. I get the sense that he’s doing what he’s doing for no other reason than to amuse himself.
Maybe it’s that quality that ironically makes his audience like him even more. “The appeal of him, and maybe the rest of the family less so because they don’t really post anything, is that he’s just a weird, weird guy,” Josephine, the former Kennedy fan Tumblr impresario, told me. “He taps into the Gen Z randomness and kind of spoofs some of it a little bit because they are supposed to be like American royalty, right? And he just does not lean into that. He brings a layer of self-awareness to this family that’s had this mystique.” Still, even she doesn’t understand some of his recent videos. “I felt like it was an inside joke that I didn’t get,” she said of the “Ticket to Ride” one. “I don’t know who this is for.”
I actually like a lot of Schlossberg’s antics, but the problem with endorsing him as some kind of savior of democracy is that his videos about his cousin are … frequently unwatchable? I do not want to watch a man, even a handsome Kennedy man, create a bunch of weird characters to explain to me how great Biden is. And another thing: He’s trying to be an edgy … Biden supporter? He’s willing to turn himself into a caricature of a himbo on the internet, but supporting fellow Irish Democrats is the part of his family’s legacy that’s beyond reproach?
Maybe Schlossberg shitposts because he resents the golden-boy image that’s been thrust upon him. As another great shitposter once wrote, “They want me to act professional on the internet. No, I won’t lol.” But K.D. plays, I’m told, excellent basketball when he’s not goofing around on the internet—does Schlossberg have some larger endgame here? For a while, I’ve been wondering why he doesn’t start a TikTok account and sort of professionalize his whole operation, go straight with it, in a place where his fans can congregate and leave comments. Lo and behold, while writing this, I discovered that he seems to have started one, and over the period of a few days I’ve watched it climb from 500-odd followers to 5,000 to, last I checked, some 45,000. Good for him. My one note is that he should find a way to be, say, 10 to 20 percent less deranged. All he needs is one friend or family member to occasionally tell him which posts to leave in the drafts. Maybe president isn’t in the cards. But I see big things for him as an influencer.
