Jack Schlossberg, John F. Kennedy’s only grandson, is more than just the heir to a storied American dynasty or a talking head on social media. With his towering frame, dark hair, and strong jawline, the 31-year-old is the spitting image of his uncle, John F. Kennedy Jr. To a younger generation, however, he is more notably the man behind a series of outré filled with colorful characters, playful ditties, and (and ) of props. “I am inspired by my family’s legacy of public service,” he tells . “I take that very seriously, and I want to contribute in my own way. I have big dreams, but I also know that I’m trying to make a positive impact today.”
Today, Schlossberg joins as a political correspondent ahead of the 2024 election, a role that will see him combine his background in law and business (he received his JD and MBA from Harvard) with the self-described “silly goose” tendencies he displays online. Galvanized by the spirit of his grandfather, Schlossberg aims to bring levity to a grave moment in American politics when many feel that democracy itself is on the ballot. For him, that means reaching an audience of young voters through amusing yet genuinely informative videos about the news out of Washington, from a breakdown of the (and its aftermath) to a recap of the . “If you’re going to ask people to think about something serious, you need to make it entertaining or fun,” Schlossberg says. “That’s what all the great leaders do. You can’t just hammer people with how bad stuff is. You’ve got to bring some positivity and good energy to the things you think are important. That’s the only strategy I have.”
Of course, for his legions of followers online, there is more to Schlossberg’s appeal than just his progressive politics: In response to the many, inquiries about his relationship status, he demurs, offering a coy “no comment.” He does share certain details about his private life, however. For one thing, he’s a voracious reader. (“I don’t know if your readers are going to love it, but it’s called and it’s about ExxonMobil…”) He is also an avid athlete—fond of water sports especially—though he’s been taking ballet recently to help rebound from an injury. He keeps his apartment stocked with fresh flowers (his favorites are carnations) and he attributes his largely colorless wardrobe to the Johnny Cash song “ ”: “Johnny Cash told me that I wasn’t allowed to ever wear anything but black,” he says.
Here, Jack Schlossberg tells about his first brushes with politics, what issues matter the most to him, and his hopes (and fears) for the months ahead. The conversation has been edited and condensed.
It was probably 2007. Obama was still a major underdog, but young people were excited about him. My Uncle Teddy—Senator Edward Kennedy—asked me what I thought of [Obama], and I said how much I loved him and thought he was the real deal. I know that my Uncle Teddy was just humoring me in a way, but I also felt like he wanted to hear the opinion of a young person and took it seriously. He and my mom [diplomat Caroline Kennedy] endorsed Obama right after he won the South Carolina primary. I felt so involved, so heard, so excited about politics, and felt that anything could happen and I could make a difference.
At that time in my life, I wasn’t good at anything, really. I was pretty bad at sports, and I was a bad student. But all of a sudden, Obama was running, and all I wanted to do was watch the news every day. I got super into politics, and I felt like it was the most exciting thing I’d ever seen. As I got older, I connected my own family history with it, and it made it all the more exciting. It felt like anything was possible with Obama because there was a bad situation, and then someone came along that everyone believed in and got behind, and then he did a great job. It seems like a quaint idea now, maybe. Everyone’s kind of had that coming-of-age with politics—of being super idealistic and then realizing that it’s a long struggle. My journey has been no different.
My grandfather, President Kennedy, is my hero. The first thing I ever got really nerdy about was him, his speeches, and his administration. I think that it’s a blueprint for how progressivism can work in America, and how America can lead the world in a positive, optimistic, science-driven way. As I’ve grown up, I’ve become more involved in the official obligations that come with being part of my family. I’ve met a lot of politicians and become all the more optimistic about our future by doing that work. I’ve connected to it on a personal level in terms of my own interests, and on a professional level as well, with the work that I do with the I’ve always felt super lucky that there’s this massive historical record about my family that I can learn from. A lot of people don’t get to have that kind of relationship with their ancestors. I’m so lucky for it, and so I try to learn as much as I can from them. I think my grandpa’s speeches are the coolest things ever. His administration actually did so much that’s still with us today, and I think that he inspired a whole generation of people to enter public service—and still does.
I was in 10th grade, taking U.S. history, and we were learning about the Kennedy Administration. I felt uncomfortable, so I was goofing off. The teacher called on me and tried to make me look stupid by asking me what the Kennedy Administration’s policy was in Laos—which I still don’t know the answer to after many years of trying to figure it out. Nobody does. I was really embarrassed. That day, I went home and started reading. That’s when I started getting serious about learning about my family and got really inspired by it. I think one gift that [President Kennedy] gave me was , his famous moon speech. That line, “not because they are easy, because they are hard,” is something that really resonates with me. I think it’s a timeless message. I just read and read and read, and it made me way smarter, and it made me a way clearer thinker. I went to law school super liberal, and I came out of the program with the same thinking—just realizing that I was still right, but that I had not known what I was talking about before. It made me much more aware of every point of view and more open to other ways of thinking. I still have the same values that I did when I got there, but I think my way of thinking is completely different. Whenever I am thinking about something, I can hear other students—the super conservative kids—and they’re not always wrong. I love it. I feel like that’s what makes life so fun. Most people are very, very smart. If you can channel people’s voices, I think it makes you smarter.
You asked earlier about my family. I feel like the one thing about my family—the legacy of it—is to try to stay positive about government, and that’s something that’s pretty lost on both sides these days. I try to stay positive, and for some reason, these days, that’s a unique perspective. I think that says a lot about our media environment. To me, if you’re going to talk about stuff, it’s a responsibility to try to make it a little bit better. I really feel like there’s such an opportunity to frame everything with climate, the environment, and energy differently. I think that they’re interconnected. I obviously believe climate change is the most important issue that we need to deal with, and I also see it as the greatest opportunity we have. There’s this battle between fossil fuels and environmentalists that I think needs to be put to rest. Everyone needs to get on the same team and realize that the environmental movement of the past was about stopping development, and the environmental movement of the future is going to be about building huge infrastructure projects like a new energy grid and renewable power sources. That’s what I studied in school: environmental law. . [Since 2019] . But at the same time, you’d never know that because we let the right wing say that [liberals] hate oil and want to make it harder to drill, that we’re all environmentalist tree-huggers and we don’t like the economy. It’s completely not true. Those two things don’t need to be set up in opposition to each other, and they can’t be if either problem is going to get solved. People need to get onboard with the idea that corporations aren’t always bad and that we’ve got to work together.
I think it goes under the broad banner of civil rights, which are under attack right now in America by the Supreme Court. is just one example of a Supreme Court that’s actually trying to go back in time and take power back for themselves. It’s completely anti-democratic and it doesn’t stop there—it goes to things like voting rights, which are under attack all across the board. That’s the biggest issue, practically, that our country faces right now: that our rights are being taken away by a fringe minority in broad daylight.
I would say it would be for others to describe. I guess I’m just having a good time. I’m a fun, wacky guy. I’m a silly goose—a silly goose who’s trying, just trying, to get the truth out there. I try to say things that I think are important. People can tell when people are being authentic and don’t have any other agenda. I think that comes through in ways that are intangible but people pick up on, especially younger people who are super fluent with social media. There are things that you can tell are authentic versus not, and I think people respond well to that with me. I think very deeply and critically about what I want to say.
This election year is so important to me, and that’s why I’ve been trying to be out there more. This is a really pivotal moment in history, and it’s such an exciting time to be alive and to be able to vote. I want to get that vibe out there because I think there’s a lot of negative energy about politics, and I want to bring some positivity out there because I think this really matters. The stakes are very high. I think there are two fundamentally different views of government being offered as choices. I’m worried. I feel like things will actually go badly in daily life if Trump wins: people will lose their healthcare, voting rights will continue to be under attack, our elections will be way less safe, and we’re going to pull out of all of our alliances. These are actual things that are going to go really badly really quickly if Trump wins, and I think that’s looking more and more likely every day. It’s going to be a lot more work for younger people in the long run to have to clean that up than it is to show up and vote one day out of the year. I really am focused on creating a positive outcome where the good guys win. It’s going to be more complicated than that, but I’m still optimistic. Things don’t have to get way worse. I don’t want young people to grow up only knowing a certain era of government where they don’t think anything can get done. Whatever people decide is up to them. I think, however, the choice that you’re actually making about the government you want is the same today as it was a month ago. It’s worth showing up to vote even if you’re not enthusiastic about the candidate so that things don’t get way worse. I understand if that’s not an appealing message to people, but I still think, at the end of the day, voting for Democrats is going to be the right way to go. There’s so many amazing people in public service right now—people who are good at their jobs—and we don’t hear from them that often. There’s going to be a new generation that enters politics in the next few years, and I think that’s really exciting.
