John Bouvier Kennedy Schlossberg, known to friends and voters alike as Jack, is thirty-three and running as a Democrat to represent New York’s Twelfth Congressional District. Shakespeare, who wrote endlessly about the inner lives of the Tudors and Plantagenets, might have struggled with the curious history play that is Schlossberg’s life of legacy and expectation. His biography blends the conventional-aristocratic—Park Avenue; Martha’s Vineyard; a Yale B.A.; a Harvard J.D./M.B.A.—with a sustained string of social-media provocations, from a riff on the “hotness” of Usha Vance to a dramatic reading of Melania Trump’s letter to Vladimir Putin, complete with a dubious Slovenian accent and a blond wig.

Schlossberg grew up amid the ambient din of people wondering if, or when, he would follow in the footsteps of his grandfather John, his great-uncles Robert and Edward, and many other relations—and, more recently, whether he would take on Robert, Jr., whom he loathes both politically and personally. Despite the somewhat wandery path of his post-collegiate years, Schlossberg finally took the leap into electoral politics last fall, when Jerry Nadler, after three decades in Congress, decided to retire. In the early going of the campaign, Schlossberg, floating on name recognition, dominated the polls, trailed by Nadler’s protégé, Micah Lasher; the anti-A.I. crusader Alex Bores; and the former Republican Never Trumper George Conway. Then, a few weeks ago, Nicholas Fandos of the Times published a front-page article that described both Schlossberg and his campaign as chaotic and undisciplined. Schlossberg’s poll numbers have been plummeting ever since.

When we met recently for an interview for The New Yorker Radio Hour, Schlossberg seemed off balance from the Times piece and the direction that the race had taken. He displayed little of the confidence of a political natural: the buoyancy and self-possession, the Clintonian focus and eye contact. And, as he made clear, the loss of his older sister Tatiana, who died of cancer last year, weighed heavily on him, too. Our conversation has been edited for length and clarity.

Jack, I first want to express my condolences about your sister, who died some time ago and wrote an extraordinary piece for us. You must miss her enormously.

I do. Tatiana was my best friend. We could finish each other’s sentences, and I miss her every day. That piece was extraordinary. She was a beautiful writer.

Why did you decide to run into the teeth of such grief?

Well, I wasn’t planning on running for office now. I wasn’t plotting and waiting in the wings for a seat to run for. It’s an unlikely path that led me here, and it kind of started at the end of 2023. I went to law school, business school. I graduated, took the bar, and I finished all that, and I thought I was going to be an environmental lawyer. I was excited, because that’s what I studied and that was what I cared about. But at the same time, I still am—and always will be, irrespective of his decision to run for a second term—a huge Joe Biden fan.

I knew the truth, which was that he had accomplished so much in the first years of his term. I mean—biggest investment in energy and infrastructure in decades, ended our longest war, ended the pandemic. And nobody knew about this at the time. And if you think back, it was a different world. R.F.K., Jr., was a Democrat running for President, and a Trump victory did not seem like an inevitability.

So I decided to go work on the Biden campaign. And, long story short, we didn’t really . . . They hired me to help with youth-voter engagement, but we didn’t really see eye to eye on video stuff. So I left the campaign—

Tell me about that. What did you want to do and what did they want you—

I wanted to go hard after R.F.K., Jr., and at the time, there was a lot of risk aversion there. So I quit, because I couldn’t live with myself if I didn’t speak out in the way I wanted to. And I got a lot of heat for that, but I knew I had to do it my way.

I spent about a month writing draft over draft about what kind of statement I wanted to release about R.F.K., Jr. And, one day, I just took my phone out and started talking to it and posted it. It went viral in a way that I never imagined, and overnight I built a fan base that I was as surprised as anyone to have.

About a month later, I got a call from the Biden campaign, asking me to come back to make more videos, to speak at the D.N.C., to be a delegate from New York, and to travel to every swing state across the country—which I wasn’t paid to do, and took upon myself. I had a lot of success doing it, and I’m really proud of that.

And it showed me that I had something to offer the Party in the kind of social-media engagement that I was getting, not because I was in an ad campaign or was a movie star, but because I was speaking truth to power about our political systems.

Do you think there are things that you did before, on TikTok, that you wouldn’t do these days, now that you’re wearing a shirt and tie and campaigning? Would you put on a blond wig and imitate Putin or do some of the crazier things you did?

Yeah, I mean, I wouldn’t call them crazy. I think satire is a really powerful political tool, and it’s not like I was making videos that nobody was watching. I was breaking through pretty well.

Yeah, you were.

And, I think, raising awareness on issues for people who otherwise might not receive that information. But the internet and social media change rapidly. The first stage of me going viral was very much happy, comedy, silly. This was a time when, you know, the ’24 election hadn’t happened yet.

You’ve said, “I’ve got a legal education and a lifetime of working on the issues I care about.” But you haven’t worked as a lawyer post—

Not at a law firm.

But, then, how so?

How so what?

How did you use your legal education?

Well, I understand that content creation is a new profession and that for a lot of people it’s not synonymous with a quote-unquote real job. But I’ve been arguing with evidence supported by facts, very clear arguments made on behalf of the issues that I think are important, and those issues are: corruption of the Trump Administration; his terrible, irresponsible foreign-policy decisions; advocating and arguing for why the Democratic Party—its history and current policies—reflect putting a priority on organized labor and working families.

And on social media, it’s not like I was successful just because of my name. You have to make an argument in ninety seconds, with a lot of complicated information. And synthesizing that information, breaking it down into one, two, and three points and having a conclusion—that’s the exercise of law school.

Jack, you know, somebody my age, my first memory is the death of your grandfather. That’s a big set of imperatives to carry on your shoulders. When did this sort of enter your life, that there was something unusual attached to your future?

There is one moment that sticks out. It’s tenth-grade history class, and we’re learning about President Kennedy, and I—

This is at the Collegiate School—

This is at the Collegiate School, on the Upper West Side. And Dr. Grossberg was giving us a lecture about the Kennedy Administration, and I felt uncomfortable, and I was goofing off in the back of class.

And she called on me, because she knew I was making trouble, and she asked me about the Kennedy Administration’s policy in Laos, and I wasn’t familiar with that at the time. And it was mortifying because I wanted . . . You know, I said I didn’t know. And I went home and started reading Ted Sorensen’s book on my grandfather, and I started listening to and watching his speeches every single day after school.

I made myself do that before I started my homework every day: listen to one speech or read a chapter of a book about him. And I got really inspired by the story that I read. J.F.K. sent a man to the moon. He drafted the Civil Rights Act, established the Peace Corps. There are so many things about the progressive agenda, supporting the arts, that he represented and that trace their origins back to the early nineteen-sixties.

But it’s a complex legacy as well, even for a liberal. Included in that is the beginnings of Vietnam, of the Bay of Pigs, all kinds of things, on both a personal level and on a political level. How do you take all that in? And I return to my original question: When did you start feeling that voice in your head, in the ambient sound of your life, that you’ve got to do something about that?

I’ve loved politics since I can remember, and I feel motivated by the call to answer. . . . You know, answering the call of public service is what President Kennedy represents. And, sure, there are complications in his legacy, and in other members of my family, but, over-all, it really stands for the progressive values that are under attack right now by President Trump. I mean, there’s a reason President Trump fixates on John F. Kennedy and our family name. There’s a reason why he renamed the Kennedy Center the Trump-Kennedy Center.

Your granduncle and godfather, the late Ted Kennedy, once ran for President, and he faced a correspondent named Roger Mudd, and he was asked a very simple question: “Why are you running for President?” And I think it’s fair to say that he kicked the can, at the very best.

That’s right. Famously.

Why are you running for Congress? You’re in my district!

Well, I’m running because I want to pass laws. I want to pass laws that help the people in this district and in our country. I want to fight for federal funding for the district New York 12, and I’ve released plans that I want to pass in Congress, like passing a renter’s deduction so people can deduct their rent from their taxes.

I wanna make H.I.V. medication free at the point of care. I wanna make the child tax credit paid out monthly, not annually, which during COVID cut child poverty to historic lows.

But have you worked on behalf of any of those causes affirmatively and spent time on them? In other words, you have opinions. We all have opinions. What have you done affirmatively that gives confidence to a voter that says, “This is a guy who selflessly worked on behalf of some of these things,” whether at a lower level of politics or in hard volunteer work where he sweated it out?

Yeah, absolutely.

Why do you deserve this seat?

Well, I think my experience is why people are so excited about our campaign. I graduated with a J.D./M.B.A. from a top university, and I went and, with that education, was a top surrogate volunteer for the Biden campaign, travelled to every single swing state in this country.

You did volunteer campaign work.

Well, yeah, but I think it’s much more significant than that. I was a top surrogate for the campaign, who travelled all over and inspired a new generation of Americans to believe in public service and politics, and overnight built an audience of millions of people just using my own two thumbs on my social media, and single-handedly inspired them to volunteer for and be excited about the Party in 2024.

Nobody asked me to do that. Nobody showed me the road map for it. And I’ve been working on causes that I care about my entire life. I’ve been representing a family legacy that is synonymous with the Democratic Party and progressive values. And in 2024—

What does that mean, beyond the sheer presence of—

That means working for and with the John F. Kennedy Library, presenting the Profile in Courage Award. This year will—

You presented the award?

Yeah. And represented my family, alongside my mother, who was Ambassador to Japan. It’s, like—it might not sound like work to some people, and I’m not saying that that’s a traditional job, but a lot of work goes into it.

As I said, I was in the middle of explaining . . . I created a platform to advocate for the Party when nobody else had been, and built a huge fan base doing that, and then created a media company with results that anyone comparable in that field would kill for. And just because I turned down millions of dollars in brand deals and book deals, because I wanted not to be bought and paid for, I don’t think that means that that’s not a job. So I think that my experience is exactly what the Democratic Party needs right now from candidates.

In your previous interviews, you’ve said that money in politics is a very important issue to you.

I think it’s the single most important issue facing our country and our party, and I think people, even the people who do care a lot about this issue, don’t care about it enough. Citizens United has fundamentally changed our country. Super PACs are a huge part of the reason why our government does not function, why we can’t get legislation passed on—

How is your candidacy funded? You decided not to take PAC money.

Yeah. On the first day of the campaign, I made a pledge: No super-PAC money. I will disavow any super-PAC support. No corporate-PAC money, no money from Big Tech or A.I., no special-interest-group money. And I said that at a time when I did not realize my two main opponents, Alex Bores and Micah Lasher, would accept tens of millions of dollars in super-PAC money, tens of millions of dollars from billionaires.

O.K., I understand that objection. But they would turn around and say, “But I’m not connected like my opponent. I don’t have Bette Midler, Lorne Michaels, Paul Simon donating to my campaign. I don’t have a personal fortune that I can draw on.”

Well, first of all, each of them are millionaires, so that is irrelevant. Second of all, we need to explain this to people so they understand. There are two types of ways money gets into politics: the hard side and the soft side.

Sure.

I’ve accepted contributions on the hard side. That means, if you or anybody—Lorne Michaels, whoever you just referenced—contributes to our campaign, that’s a hard-money contribution that is limited at $3,500 for a primary, and it has to be disclosed. That is fundamentally different from a super PAC, which can raise and spend unlimited amounts of money, and it’s often not disclosed.

That is how you get campaigns that can raise tens of millions of dollars. We have outraised our opponents on the hard side, the campaign side, and people don’t understand that even though we’ve outraised them, and we’ve raised three million dollars—which is in the upper echelon for any congressional campaign—that leaves us with a budget for paid media for the entire campaign that is less than what my opponents regularly spend in a single day.

It’s also very important to remember that Alex Bores is backed by a guy named Chris Larsen. Chris Larsen has a company called Ripple. Ripple has a super PAC that is actively funding Trump MAGA candidates around the country, five of whom just won their primaries. And Micah Lasher’s super PAC is funded by a billionaire who just spent tens of millions of dollars against—

Who is that?

Michael Bloomberg, against Mayor Mamdani, trying to defeat the Democratic nominee for mayor in the last election.

But Michael Bloomberg has also supported plenty of Democrats in terms of funding.

True, but I don’t think that—it doesn’t really make a difference for me if you’ve supported some Democrats if you’re also actively supporting Republicans around the country. You gotta pick a side right now.

Jack, you were ahead in the race by five points.

Or eight or ten.

And now you’re behind.

According to some polls.

There was a precipitous dip. And what seemed to happen is—there was a piece in the Times that, among other things, described your campaign, with a lot of reporting, as disorganized. After that article was published, your poll numbers took a big hit. How do you respond to that Times piece?

There’s one thing that is accurate in the article, and that’s that we’re different from the other campaigns, and that’s by design. Most people don’t know how campaigns are structured. A typical campaign has a campaign manager, and then probably ten different consulting firms, a compliance firm, a mail firm, a TV firm, a digital firm. And that’s the kind of structure that I started with in the outset. These stories and anecdotes date back to the end of November, early December, when I hired several consulting firms that I quickly realized did not have much to offer me, and I quickly decided to part ways and build a campaign structure that worked for me.

And look, that piece, printed on the front page of the New York Times, with a lot of anonymous sources, no accusations of any wrongdoing. I’m not here to complain about my press coverage, but I wish the media would cover my opponents with half the level of scrutiny that our campaign has gotten. The idea that I slept through my launch day is demonstrably false. And anonymous sources and disgruntled employees describing a campaign as erratic and chaotic—well, not many people can keep up with the pace that we set.

Any congressperson, if they get one initiative to the top of the heap—not just in one term but in five terms—is lucky, unless they’re Nancy Pelosi or somebody like that. Certainly a freshman. So what would be the absolute top priority that you would be absolutely focussed on?

Well, I will answer your question, but I will start by saying that I don’t think we can afford to set our sights on just one issue, and that the Democratic Party is about to face a question of whether or not we hold President Trump accountable, whether or not we try to impeach him and investigate and prosecute his Cabinet for the crimes that have been committed.

So you would move to impeach President Trump.

Absolutely.

For what?

For bribery. He’s made four billion dollars so far this year, him and his family. He has signed contracts and made deals with foreign countries, after which his companies, his sons’ companies, have received preferable treatment, equity stake in large companies from those exact foreign governments.

He has a cryptocurrency in his own name that he has sold using the power of the Presidency. Bribery is specifically listed in the Constitution as a crime justifying impeachment. So the jet from Qatar; the stake in the tungsten mine, in Kazakhstan, that the Trump family organization has taken; the stock trading that the President has engaged in, especially recently, in massive tech stocks, ahead of a visit to China—all of these things demand investigation, and we have to hold him accountable, and that’s a difference between me and the others running. The person leading in the polls right now, Micah Lasher, does not think impeachment is worthy of the Democratic Party’s time. He thinks it’s a futile effort. He thinks it’s gonna be too hard. I think that we have absolutely no choice.

Do you think members of Congress should be able to trade stocks?

Absolutely not. I think that’s—

Does it worry you that Nancy Pelosi, who’s probably your most prominent endorser, has done better in the stock market than one could even possibly imagine?

I think Nancy Pelosi is the backbone of our party, and she exists in a system where she did nothing illegal. I wouldn’t trade stocks. But I’m not about to sit here and question and dismiss the tactics of the most effective progressive leader the Democratic Party’s ever had, certainly in my lifetime.

It’s not possible to both praise and at the same time criticize somebody like that?

I would not emulate her. I would not emulate her stock trading myself, and I think that’s the—

So what would you do? You have substantial means in your name. What would you do with those means in Congress?

I would put them into a blind trust that I was unable to trade.

Fair enough. You’ve been questioned about your stance on Israel, and called out for being a little inconsistent, so I want you to set the record straight. There was a piece in Politico recently. You’ve criticized Benjamin Netanyahu, the Prime Minister of Israel, and you said, I believe, that you wouldn’t send offensive weapons to Israel—there’d be no trading in that—but that you would support a continuation of the Iron Dome as a defensive measure. You see a lot of tension in New York City in particular on this issue. How have you changed, or not, in your over-all view of Israel?

I’m completely consistent no matter who I’m talking to about my views on this question. My stance on the U.S.-Israel military relationship has changed as the situation has changed, just as it has changed for A.O.C. and for Bernie. The Iran war marks a turning point. On the day the Iran war was initiated by President Trump, I said that I oppose the war. Opposing the war means opposing all funding for that war, including sending offensive weapons to Israel, with whom we are jointly operating in Iran.

So Iran under Donald Trump was the breaking point, not the behavior of the United States during Gaza when President Biden was in office?

Well, I think this is a very complicated situation in the Middle East. There are many factors contributing to the violence and war-making that is going on there. When the U.S. involvement in the region reached a fundamentally different threshold level, that is when I decided to say, “Stop sending bombs. Stop sending offensive weapons to—”

I guess what I’m asking is, were President Biden and Kamala Harris too easy on Netanyahu when they were in office?

I wouldn’t go that far. I think that it’s always easy to second-guess policy, but President Biden was a strong supporter of Israel. Certainly more could have been done to protect lives in Gaza, but I also believe that President Biden was able to get humanitarian aid into Gaza in a way President Trump refused to do, and that they did more to limit the loss of life there than President Trump has. So their record may not be perfect, but that’s how I see it.

Do you think history will be kind to President Biden when it comes to Gaza?

I don’t think that history will be kind to the U.S. when it comes to Gaza, but I do think that over time the situation has changed. In the year following October 7th, I think there was a fundamentally different situation, where Israel had been attacked, and they were justified in defending themselves. I don’t think the U.S. should continue supporting offensive weapons [going] to Israel, or their settlements in the West Bank, but we should not abandon our ally full stop. Israel is our historic ally. I hold out hope for a better future for the U.S. and Israel, and I also believe that we cannot afford to . . . For the same reason I oppose sending more offensive weapons, I support funding for the Iron Dome. It protects civilians—including six hundred thousand Americans who live in Israel.

You’ve backed Mayor Mamdani a number of times, right? In earlier races as well.

Yeah, I’m the only candidate who endorsed him before the mayoral primary.

And he describes himself as a democratic socialist, as Alexandria Ocasio-Cortez has, as well. Do you see yourself as a socialist, or a capitalist, or how would you describe your ideology?

I’m a Democrat and I’m an American and a New Yorker. I don’t . . . Those labels, I don’t subscribe to those labels.

They’re not just labels—they’re descriptors that have meaning.

Well, again, I’m a Democrat. I’m not a socialist. I believe in capitalism.

Fair enough. Jack Schlossberg, thank you so much.

Thank you. ♦

The New Yorker Radio Hour is a co-production of WNYC and The New Yorker.