Yahoo News What’s Eating Jack Schlossberg?
Tracking down John Bouvier Kennedy Schlossberg is not easy. Even though he is a ubiquitous presence on social media, Jack, as he’s called, is tough to find IRL and even harder to get on the phone. I spent most of the spring and early summer trying to reach the 31-year-old scion of America’s most illustrious political dynasty (and graduate of Yale, Harvard Law School, and Harvard Business School) to see, well, if he’s okay or whether he’s lost his mind, given the series of bizarre videos he’s been posting lately on Instagram and TikTok.
“Can you tell him to email me in a month?” he wrote to a mutual friend in April. I seemed to be getting somewhere. This might happen, I thought. As instructed, I emailed him in early May. He didn’t respond. Somewhat discouraged, I tried him again a few weeks later, right before Memorial Day weekend. “Sure, here’s my cell,” he replied. “Could you call in an hour? Also, can we stick to 5 mins?’ Of course we could, I responded, somewhat disappointed that our chat might be so short. Then I realized that he hadn’t included his phone number in the email. Jack, how about that phone number? He quickly shared it. Then there were the requisite voicemails left. A breakthrough was close.
I’d never met Jack before, but I still felt somewhat protective of him. I grew up in Massachusetts, where the Kennedys were—and remain—revered. I met his grandmother, Jackie, on a few occasions, much to the delight of my mother, who like many women of that time tried to emulate the former first lady. I once changed a flat tire for Jack’s mother, Caroline, when she was a Harvard undergrad. (She has no recollection that I helped.) I was a high school friend of Jack’s late uncle, John F. Kennedy Jr. In fact, Uncle John was one of the main characters in my 2019 book, Four Friends, about four of my Andover classmates who died young and tragically. I thought it would be fitting to speak with Jack, if I could, as we were approaching the 25th anniversary of John’s senseless death off the coast of Martha’s Vineyard.
When we finally spoke, Jack was open, gregarious, and charming. In that way he reminded me of JFK Jr. He also, like his uncle, is smart and spoke in complete sentences. Jack told me he had just moved to Louisiana (!), some 45 minutes outside New Orleans. He headed down to the state six months ago. “I absolutely love it,” he told me. “It’s getting to know a different part of the country, and that’s been so much fun for me.” He had just moved out of his parents’ Manhattan apartment into his own apartment but then, after three months, he decided to up and leave. [After this interview, Jack informed T&C that he has “things going on in Louisiana but is back in his Chelsea apartment now.”]
He also told me he has been auditioning for acting roles—he declined to say which ones—something his uncle had done at Andover and Brown and briefly in New York City before becoming an assistant district attorney. Unlike Uncle John, Jack passed the New York bar exam on his first try. “Lots of people are saying I scored in the top 1 percent with a 332,” he told me, with deserved pride. He also said he has started writing a book, although he doesn’t have a publisher for it yet. “My book is about my method and how I see the world.” He declined to discuss his dating status.
Once we covered the basics, Jack agreed to talk about his videos, which, if you haven’t seen them, run the gamut. Poke around his profile pages—they're not private—and you’ll find him sashaying shirtless in one video to the Beatles’ “Ticket to Ride,” like a male version of Little Edie Bouvier Beale in Grey Gardens. In others he makes unapologetic attacks on the independent presidential candidacy of his cousin Robert Kennedy Jr. while pledging his unequivocal support for President Biden.
But the videos that are getting him some perhaps unwanted attention (or was that part of the plan?) include a recent group of Instagram reels in which he imitates the voices and ethnic mannerisms of a variety of stereotypical white males. There’s Jack, unshaven, driving a car and imitating a Russian named "Vlad" who believes that Bobby Kennedy Jr.’s candidacy is good for Putin and Russia. There’s Jack as “Joshua,” an older Jewish man, presumably from New York City, who doesn’t understand why anyone would vote for Bobby Kennedy Jr. “Wade,” a Southerner with three daughters who doesn’t want them growing up with “President Trump 2.0 grabbing stuff.” “Anthony” (or “Antny,” in Jack’s locution) is an Italian guy from Long Island who says, “Listen, who doesn’t like the Kennedys? But listen to me. This guy [RFK Jr.]. This guy…” And finally Boston-accented “Jimmy,” from Southie, who cares about three things when deciding who to vote for for president: the economy, the environment, and the reproductive rights of women. “I believe Joe Biden’s economic record is second to none,” he says. Jimmy also—curiously—calls Bobby “a prick.” And then he says, “I’m a tree hugger” but that he also “loves freakin’ oil” and “that’s not a contradiction.”
Even when he posted them, Jack seemed to know the videos would be controversial. He is the only grandson of President John F. Kennedy, and many people think (or hope) he has political aspirations of his own. And his mother is in politics. She’s Biden’s ambassador to Australia and was Obama’s ambassador to Japan. In another video Jack asked himself, rhetorically, if he “really wants to do this” because he’s “playing with fire.” His conclusion? Yes, he does.
Of course that was his answer. He’s a Kennedy. In my experience there are just different rules for his family—or the rules that exist for others don’t apply to them. That’s been the case pretty much since the patriarch, Joseph Kennedy, became one of the wealthiest men in America, then the U.S. ambassador to England during World War II and the first chairman of the Securities and Exchange Commission. For generations Americans have cut this one bloodline—the whole rich, good-looking, powerful, tragic family—a whole bunch of slack.
At Andover we definitely gave John-John enormous latitude when he had lapses of judgment, because he was so rich, handsome, charming, etc. We all thought we knew him: We’d seen him saluting his father’s casket. He was everyone’s little brother who we knew would grow up to become a prince. Regarding Jack, I think it’s safe to say that if the son of any U.S. ambassador without Kennedy in his name had made such videos, there’d be raised eyebrows at the State Department and in the media. The woke police would be swarming.
But no one’s complaining about Jack. Mostly it has just become a curiosity, a head-scratcher. There were articles about the videos in the New York Times and the New York Post. And questions on social media. For instance, GoddessFianna, writing on Reddit, thought his recent Instagram videos “have been weird” and that she has “the feeling he’s an eccentric dude, but the stuff he’s posting and the way he’s acting almost seems like he’s going through something.” She asked if anyone had any insight into him and his antics. A TikTok of him vibing, in sunglasses and a backward baseball cap, to a talented amateur’s live acoustic version of U2’s “With or Without You” got this response: “Looks of JFK Jr with the heart of Little Edie ♥️”
The family friends I talked to about Jack wonder just what he’s doing. “When he does working-class accents, he’s playing with fire,” said one. “Here’s this rich kid making fun. So that’s probably another problem he has to deal with.” But then the friend acknowledges the impersonations aren’t half bad. “He’s got all the stuff. He’s got the humor and the talent and the intelligence to be a really powerful force on social media and against Bobby. I just wish he’d kind of get it together.” Another longtime family friend seemed a little exasperated by it all. “He’s a good kid,” the friend said. “But I do not understand what he’s doing. I watched a little. People sent it to me. I have no fucking idea… People do really stupid shit and they do it when you think they’re too smart to do it.”
Jack doesn’t care if people are offended or if they think he’s a weirdo. That’s intentional, he says. He seems to enjoy the attention, in the same way Uncle John did before he got married and before he and his wife Carolyn were hounded mercilessly by the media. The videos have been a “huge, huge success,” Jack told me. “I think I’ve broken through to a younger audience. I think everyone’s looking for a little bit of levity and humor here, and if it’s all so serious all the time, it’s just too heavy.” The idea, he explained, was to convey his serious thoughts about the upcoming election in a funny and entertaining way. “I think a lot of people are confused, but I think a lot of people understand what I’m doing.”
That makes sense for the election-related videos. But what about the others? The one with Jack, in Hawaii, working hard to open a coconut with his bare hands, and succeeding. Or another, where Jack, sweaty, is just back from a run, wearing a T-shirt with the word “Funcle” on it, while nearby a flutist plays the theme from The Godfather. There’s Jack in some wood-paneled cafeteria explaining why he doesn’t like Italian food. There’s Jack, last July 3, on some island in the rain (Martha’s Vineyard?) ranting to his mother about how much he hates going out to restaurants. In this so-called “resta-rant,” Jack declares his “independence” from “ever going to a restaurant again.” Why, his mother asks him, kind of egging him on. “What’s wrong with going to a restaurant?” He says that going to restaurants is both “stupid” and “corrupt.” His mother chuckles, while Jack continues, “Let’s go to a fancy restaurant in the middle of the day. How does that sound? We’ll sit down in a chair for a couple hours and we’ll wait. And we’ll sit there and we’ll wait. And we’ll spend three hours there, but we’ll eat our food in five and a half minutes. And then when we get up, we’ll feel sick and we can’t do anything later. And then we won’t really want to eat dinner. And then the entire day is ruined.”
It’s funny. Or at least I think so. Jack has great timing, and he’s a natural in front of the camera even when things get more cringe. In a “Hey, Dad” series, Jack asks his obviously annoyed father, Ed Schlossberg, existential questions while he’s reading the newspaper or in the kitchen—questions that probably should be answered, you know, privately and off-camera.
“If someone is treating someone else in a way I wouldn’t want to be treated, should I step in?” Jack asks. His father doesn’t answer.
“Hey, Dad?” Jack asks in another video. “Yes, Jack,” his father responds, in a bit of pique. “Should I do what I love, or what you want me to do?” There’s no response.
On Twitter, or X as it is now known, Jack (he has no blue check) has 59,400 followers, who he treats to such off-the-wall observations as there is “soooo much SALAD in Washington DC no?” He has wondered whether AI is “sexual”? And if it’s not, “does that limit its potential or make it unstoppable?” He doesn’t like electric vehicles because “they’re dumb,” and Teslas “make me car SICK” and have a “VERY sexual aesthetic (in a bad way).” (Maybe Elon personally denied him the blue check.) He has written that he drives a Toyota and that “nobody’s done more for enviro than TOYOTA.” Jack was a history major at Yale, with a focus on Japan. After graduating, he spent a year in Japan, working for Suntory Holdings, the beverage conglomerate, and Rakuten Inc., an e-commerce company. So maybe he just likes Japanese things.
He’s not blowing himself up, he told me. His social media posts about the upcoming presidential election contain messages that are important, and important to him. “I can’t sing and I can’t dance, but I can do accents and I’ve always been able to,” he said. “I’m just trying to use the tools at my disposal to get out a message that I think is super-serious and important, and that is that a vote for Bobby Kennedy Jr. is a vote for Donald Trump.” He said this is a “two-man” race between Biden and Trump, and everything else is a distraction. “If you can get that message out there, in whatever way works, it doesn’t make it any less serious, or any less strategic, to get more people to watch it. And so that’s really all I’ve been trying to do. If I wanted to blow myself up, I could be doing a lot more, and I don’t want to do that. And I wish none of this was happening. And I wish that Bobby wasn’t running and people weren’t being confused by him and led to believe that there was some other answer, or that the Democratic Party wasn’t behind them, or that Joe Biden hasn’t been a fantastic president.”
Jack said he wishes there were more young people talking about Biden’s record of success. He thinks the Democratic Party needs a better social media and messaging strategy to make sure people understand Biden’s accomplishments. “I think it’s up to all of us to try to do what we can,” he said. “And this year, for me, that meant making these videos online. I’m trying to do whatever I can to help President Biden win.” He said he’s been getting “tons” of responses from people “cheering me on” and “telling me that I helped them see something they didn’t necessarily see before. If I get one person to think that, that’s a huge success, and I think there’s a lot more than one person.”
He said he’s “very interested” in how information travels across the Internet and that his recent videos were a bit of an experiment in watching how messages move online. “It’s a lot harder for a positive message to spread than it is for a takedown. I think that if there was anything strategic about my videos, it was to try to combine those two things so that a strong opinion, which travels fast online, was combined with a serious set of facts. And I think that you need that combination in order to break through, and to make things exciting.”
Young people, he pointed out, spend huge amounts of time online. “And they need to be given a reason, and need to be equipped with arguments for why they should be doing what they’re doing,” he said. “And I think that that’s kind of what I was trying to do with my videos, was give people a real argument that they can feel comfortable voting for Joe Biden, because there’s not enough positive messaging online about him.”
He said he’d love to be doing “even more” for the Biden campaign and would if he were asked directly to participate. “But that’s not only my decision,” he said. “There are other people involved.” For the record, Jack is not currently involved in any official capacity with the Biden reelection campaign. (In an interview Kevin Munoz, the senior Biden-Harris campaign spokesperson, told me that the campaign has engaged with Kerry Kennedy, one of Jack’s many cousins and Bobby Jr.’s sister, to lead the family’s pro-Biden and anti-Bobby efforts, as has been reported in the New York Times. “I love Bobby,” she told the Times. “It’s heart-wrenching to be in this position.”)
It’s not as if Jack is never serious. His foray into political influencing started about a year ago, when he recorded the kind of scripted message that you’d expect from a Kennedy about an upcoming presidential election. “President John F. Kennedy is my grandfather,” Jack said in the video. “And his legacy is important. It’s about a lot more than Camelot and conspiracy theories. It’s about public service and courage. It’s about civil rights, the Cuban Missile Crisis, and landing a man on the moon. Joe Biden shares my grandfather’s vision for America that we do things not because they are easy, but because they are hard. And he is in the middle of becoming the greatest progressive president we’ve ever had.” Then, like a pro, he rattled off Biden’s various accomplishments during his first term.
It was a direct, articulate, and sober message, the kind of public endorsement you would expect from a scion of the Kennedy clan. It was also similar to Jack’s few other previous public appearances, for instance when he and his mother jointly announced the annual Profile in Courage Award at the JFK Library, on a spit of land overlooking Boston Harbor. Jack, dressed in a dark suit, white shirt, and thin, dark tie, stood at the lectern, cracking a few jokes, praising the selflessness of others, and looking every inch the graduate of two Harvard professional schools and the future politician that many people would love to see him become.
In those moments Jack reminds me of John Jr., especially the time when, at 27, John introduced his uncle, Senator Ted Kennedy, at the 1988 Democratic Convention, to wild applause. It’s not the only way Jack reminds me of John. He looks a lot like him, for starters, if somewhat less chiseled. They both enjoy (or enjoyed) seemingly outlandish stunts, especially on the Hudson River, despite the big ships that traverse those waters; John liked to kayak on the Hudson, Jack prefers paddleboarding. In 2017 he paddled the 25 miles around Manhattan (for charity) and wrote about it for New York magazine. (It took him almost five hours.) They both went to law school, and neither really wanted to practice law. John started a magazine, George; Jack wrote regularly for the Yale Daily News and now clearly seems keen on exploring other forms of media. And, of course, both harbor (or harbored) political aspirations. There are differences, too. John’s risk-taking tended more toward physical danger: the crazy kayaking trips to the Arctic Circle and to Scandinavia; flying and then crashing a crazy whirlybird contraption; and, sadly, piloting his own plane to his death. Jack’s risk-taking seems more of the intellectual variety. And John liked to stick to the Kennedy family tradition of discretion and mystery; Jack seems to delight in turning it on its head.
A number of older folks I spoke with about Jack and his social media presence appeared to be baffled by it. They think he’s being way too unconventional and edgy and may be doing himself more long-term harm than good, especially if he aspires to a political career. Some think what he’s doing is absurd; others think he looks like a movie star. Of course, the older generation could be just plain wrong. He could be having a big impact on his generation. But they also think that given his DNA, his youth, his intelligence, his looks, and his megaphone, he could have an even greater impact. They think, for instance, that if he teamed up with his mother—she’s back in the United States for the summer—the duo could be incredibly powerful and effective surrogates for Biden. (She would have to give up her ambassadorship to participate in the campaign.) Jack agreed. “And that’s something you may see from me,” he said.
Before we hung up, I asked him the question everyone wants the answer to: Has he thought about going into the family business? “Not anytime soon,” he said, “but I love politics. I love public service. I’m inspired by that legacy of my family. But I have no immediate plans.” His focus now, he said, is to do what he can to help President Biden get reelected. “My purpose has been, the entire time, to help people see how great President Biden has been, and to try to get young people to vote for him,” he said. “That’s incredibly important. I think this is the most important election of our lifetime. And I think that voting for Bobby is voting for Trump, and I think that’s not the right path for us to take, and that my goal, and what I wake up thinking about every day, is, ‘What can I do to help President Biden get reelected?’ I think I’ve done something.”
He certainly has.
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