For Jack Schlossberg, it can seem like his grandfather still gets top billing. But the 33-year-old grandson of the late President John F. Kennedy is out to make a name for himself. John Bouvier Kennedy Schlossberg is running for Congress in New York’s 12th district, the seat of retiring Congressman Jerry Nadler.
Schlossberg says, to those who may be thinking Oh, man, not another Kennedy, “People can think whatever they like. But I’m me. I’m Jack Schlossberg. And I’m proud of where I come from. But that’s not the only thing about me. I’m my own person, so you can count on me to think for myself.”
That may be. But he’s also inescapably a member of a family with the longest running storyline in American politics.
In just the last year, RFK Jr, a longtime vaccine skeptic, joined the Trump cabinet as Secretary of Health and Human Services; many of his own family members publicly rebuked him. Schlossberg said, “My cousin, RFK Jr., tries to pretend that he embodies a progressive agenda, when he’s in fact using his last name and lending it to President Trump, who is dismantling everything my family stood for.”
The Trump Administration hasn’t just targeted programs championed by JFK and his late brothers, Robert Sr and Teddy; President Trump also declassified files related to JFK’s assassination, then added his own name to the Kennedy Center before announcing it will close (he says for renovation).
According to Schlossberg, “That name, the ‘Trump Kennedy Center,’ is not gonna last.”
“Do you think that Trump is gonna have it razed to the ground?” I asked.
“I think he could easily demolish it,” Schlossberg replied. “He’s trying to kill JFK. JFK will never die, because he’s kept alive by the people who are fighting, organizing, and rising up now to remove Trump from power.”
Fighting words from someone who’s amassed an army of two million followers on social media:
… with some posts that are plain old silly; others that seek to educate and are positively wonky; and still others that have been more polarizing.
Schlossberg said, “You need to be aggressive right now to get your message through.”
He was asked if he crossed a line by posting a picture of Vice President JD Vance’s wife, Usha Vance, in which he superimposed his face on one of her kids. “I think what’s crossing a line is the propaganda that we see issued every single day by the White House and Vance,” he replied. “So, what are we gonna do – hold back? Hold back on our sense of humor and not tease them, make fun of them back?”
So, there is no line? “The line has been – first of all, I don’t think anyone was seriously thinking that I meant that we did actually have a love child!” he said. “You can point at anything I posted, I will point you back at a president who shares pictures of himself bombing U.S. citizens with fecal matter. This is a new era we’re living in.”
It’s time, Schlossberg says, for Democrats to take the gloves off. “You know what they’re doing to New York? They’re cutting off the funding that supports all the infrastructure for this city. They’re making New York and other blue states pay more just because they don’t like us. And what, I’m not supposed to make fun of JD Vance and his family? Why?”
For Schlossberg, politics is personal: “My grandmother wasn’t elected; my Uncle John wasn’t elected. People feel absolute free reign to say whatever they want about them. So, I’m gonna throw it right back at you. Because you know what? The time is not now to hold back, sit on your hands and say, ‘Hmm, okay. Well, why don’t we just play it safe?’ Absolutely not! We’re gonna get these people out of here.”
“He’s the outsider in this race”
Jack Schlossberg calls one of America’s most prominent Democrats, who’s also his mother, Caroline Kennedy, and his father, artist Ed Schlossberg, his most trusted advisers.
“He’s willing to take the consequences of what people think,” said Kennedy. “We need people who can reach a new generation. We’re not doing it with just boring talking points. And so, he has been able to connect with people. He’s been able to show that he thinks for himself.”
There are about a dozen candidates running for the Democratic nomination for this district. Yet, Schlossberg does not have a formal campaign organization, or even a campaign manager. Asked if she thought this was wise, Kennedy replied, “Well, I really trust Jack. I trust his judgment. Some of the other people have been preparing for this for years and years. But he came to this new. I mean, he’s the outsider in this race, actually – which is ironic. Yeah, ironic! And I think, you know, people might laugh when they hear that, but it’s actually true.”
An outsider with the education of an insider. Schlossberg has a degree in history from Yale, as well as a law degree and an MBA from Harvard. With that education, he could do many things that don’t involve running for office. “Yeah, I think he’d be great at this, though,” Kennedy said. “I mean, we need people with that kind of education, and we need people who are really informed and bring a set of values and have the courage to speak up. And I think Jack does all those things.”
“And a sense of humor!” added his father, Ed.
While he was growing up, his parents did their best to keep him out of the spotlight, though Schlossberg’s first communion did appear on the front page of the New York Daily News. “You shoulda been there. It was an amazing event!” he laughed.
That sense of humor has helped him through some challenging periods. There was a debilitating back injury in his 20s. “I blew out my back and my hip, and I had to get my whole hip reconstructed with two different surgeries. And I couldn’t really walk for about four years. But at the same time, in the metaphorical sense, strong backbone. Spine like a ramrod!”
What “family” is
For his family, which also includes older sisters Rose and Tatiana, Jack has been something of a cheerleader-in-chief. Ed said, “We’ve been through a lot of really difficult periods in our life, and he’s always there to lift it up and remember where we are, and we’re still here.”
Schlossberg announced his candidacy this past November, just one month before his sister, Tatiana, died at 35. She described her battle with cancer in an essay in The New Yorker magazine.
Asked how Tatiana felt about his candidacy, Schlossberg replied, “I can tell you now that she’s still rooting for us, and that the last thing that she said to me was, ‘You better win.’ No one knew me better, and I knew no one better than her.”
What was it like growing up with two older sisters? “It’s brutal. Absolutely brutal!” he said. “They don’t let you get away with anything. My style’s never good enough. I’ve never gotten an answer right in my entire life. But in all honesty, they taught me everything I know on how to be a strong person. And it’s also made me more conscientious and aware of my own privilege and position as a man in a world that often rewards certain types of behavior and certain people.”
In his small New York City apartment, he keeps images of Tatiana at his bedside. “Her wedding was in Martha’s Vineyard at my family’s house, my grandmother’s house there,” he said. “It was awesome. And her husband, George, is awesome.”
Campaigning is one of the few things that can pull him away from Tatiana’s two young children. Asked what kind of uncle he is, Schlossberg replied, “The best one!”
Jack Schlossberg’s family, and particularly his memories of Tatiana, at once cheer him up and spur him on. “We’re a really close family,” he said. “For me, when you talk about the Kennedy family, it’s a lot of people I don’t know. When you talk about what ‘family’ is, it’s me, my sisters, my parents. We’re a unit, and we’re really close.”
I asked, “When they say the Kennedy family, you think of those photos with, like, a cast of thousands. And you guys usually aren’t in those photos?”
“Yeah, we’re not really in those photos,” he said. “That’s a lotta, I mean, I don’t wanna, it’s all good. But you know, family is complicated.”
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Story produced by Mary Raffalli. Editor: Jason Schmidt.
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