The New Yorker Radio Hour - Jack Schlossberg, the Kennedy Running for Congress in New York

Episode Date: June 5, 2026

Jack Schlossberg, the grandson of John F. Kennedy, was one of a number of Kennedy family members who spoke out against the policies and the character of Robert F. Kennedy, Jr. Schlossberg became a public figure on social media, often trolling the right, doing his imitation of Vladimir Putin, or claiming that Usha Vance was carrying his baby. But, when Schlossberg decided to run for an open seat in Congress, critics pointed to his lack of experience in governing, or even holding a job. In some ways, Schlossberg seems a test case for how social-media influence may translate into electoral politics. “I understand that content creation is a new profession, and that it’s not synonymous for many people with a quote-unquote real job,” Schlossberg tells David Remnick. “I think that my experience is exactly what the Democratic Party needs right now from candidates.”  Further reading:  “How a Congressional Primary Became a Proxy Battle Over A.I.,” by Gideon Lewis-Kraus “ ‘Love Story’ Is a Forgettable Elegy for Gen X,” by Doreen St. Félix “A Battle with My Blood,” by Tatiana Schlossberg   New episodes of The New Yorker Radio Hour drop every Tuesday and Friday. Join host David Remnick as he discusses the latest in politics, news, and current events in conversation with political leaders, newsmakers, innovators, New Yorker staff writers, authors, actors, and musicians. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Hi, it's David Remnick. Please join us for a live taping of the New Yorker Radio Hour at the 25th anniversary of the Tribeca Festival. I'll be there with the former Obama speech writer and co-host of Pod Save America, John Lovett. We'll talk about the state of the nation and the state of podcasting and much more. The show is Wednesday, June 10th, and tickets are available at Tribecafilm.com.com slash audio. Tribecafilm.com slash audio. See you there. The New Yorker Radio Hour is a co-production of WNYC and The New Yorker.

Welcome to The New Yorker Radio Hour. I'm David Remnick. Even now, the Kennedy family appears in the media as the nation's royal family, a mix of political power and celebrity legacy as persistent in the modern American story as the tutors and the plantagenets were in Shakespeare's history plays. Six members of the family served in Congress. President John F. Kennedy remains a revered figure, and his brother Robert F. Kennedy was likely on his way to the White House when he, too, was assassinated. Bobby's son, a Kennedy of a very different ideological stripe, was running for president when he opted for an alliance with Donald Trump in exchange for a cabinet post running health and human services.

And you know what that's entailed. Several Kennedy family members have spoken out against R of K's policies and his character, including his cousin, Jack Schlossberg. Schlossberg, who has a law and business degree from Harvard, became a public figure through social media, occasionally trolling the right, like when he claimed that Ushah Vance was carrying his child. But when Schlossberg decided to run for Congress,

the attention became a lot more focused and more critical. Recent reporting in the New York Times suggested that he was not only inexperienced in politics, but unprofessional as a candidate, and that's a conclusion that Schlossberg disputes and will discuss. He seems in some way a test case for how well or not social media influence can translate into electoral politics. The seat he's running for is also my district in Manhattan,

and whoever wins it will be my representative in the House. So I was eager to speak with Josh Schlossberg. Jack, I first want to express my condolences about your sister, who died some time. and wrote an extraordinary piece that she just sent to me. I don't know what I did to deserve that. And I don't think we changed five words in the whole thing. It was extraordinary.

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, and it was classic Tatiana, who wrote it, didn't think it was good,

and then sent it in, and it didn't need any edits. And I think, you know, I remember reading that it was one of the top. read stories on the New Yorker page. It was. And, you know, she was such an admirer and longtime reader of the New Yorker. And I know she, her dream was to be published in that publication.

And so I think it was fitting that she, and only she could make such an impact with her writing. 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. You know, 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. And I was excited because that's what I studied and I cared about. But at the same time, I still am and always will be irrespective of the decision to run for a second term. I'm a huge Joe Biden fan. And I knew what, I knew the truth, which was that he had accomplished so much in his, 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. Like, RFK Jr. was a Democrat running for president, and a Trump victory did not seem like an inevitability. And so I decided to go work on the campaign, the Biden campaign at that time. 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. about that. What did you want to do and what did they want you to do? I wanted to go hard after RFK 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. So I, you know, I spent about a month writing over draft, over draft, over what kind of statement I wanted to release about RFK Jr. And one day I just picked up my phone out of my pocket and started talking to it and posted it. He's trading in on Camelot, celebrity, conspiracy theories, and conflict for personal gain and fame. I've listened to him. I know him. I have no idea why anyone thinks he should be president. What I do know is, his candidacy is an embarrassment. Let's not be distracted again by somebody's vanity project. And, you know, it went viral in a way that.

I never imagined. And overnight, I, you know, I built a fan base that I was as surprised as anyone to have. And about a month later, I got a call from the Biden campaign asking me to come back to make more videos, to speak to the DNC, 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 I took upon myself, and 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, you know, not because I was, was in an ad campaign or 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 now and now that you're wearing a shirt and tie in campaigning? Do you put on a blonde wig and imitate Putin and some of the crazier things you did? This is me, Vlad. I just want to say again point I'm making stories.

This is why I vote for RFK Jr. I am from Russia. He is hero of Russia. Yeah, I mean, I wouldn't call them crazy. I think satire is a really powerful political tool, and I think that it's not like I was making videos that nobody was watching. I was breaking through pretty well.

Yeah, you were. And I think, you know, raising awareness on issues for people who otherwise might not receive that information. But, you know, the Internet and social media changes rapidly. The first stage of me going viral was very much happy, comedy, silly, and this was a time when, you know, the 24 election had not been finished yet. You've said, I've got a legal education in 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 think, you know, I understand that content creation is a new profession and that it's not synonymous for many people 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 history and current policies reflect putting a priority on organized labor and working families. and, you know, on social media, it's not like I was, you know, successful just because of my name. You have to make an argument in 90 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 in my age, my first memory is the death of your grandfather. That's a big set of imperatives to carry on your shoulder. So when did this sort of enter your life?

that you had this, there was something unusual attached to your future. There is at one moment that sticks out in my life, and it's 10th grade history class. And we're learning about President Kennedy. 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 in the back 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 I started reading Ted Sorensen's book on my grandfather, and I started listening and watching to his speeches every single day after school. And I made myself do that before I started my homework every day

was listen to one speech or read a chapter of a book. And I got really inspired by the story that I read. And, you know, JFK sent a man to the moon. He drafted the Civil Rights Act. the Peace Corps. There are so many things about the progressive agenda supporting the arts that he represented and that started or traced their origins back to the early 1960s. But it's a complex legacy as well even for a liberal. Yeah.

Included in that is the beginnings of Vietnam, 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 do 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 overall, 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. Now, I guess he was your grand uncle and godfather, the late Ted Kennedy, once ran for president, and he faced a correspondent named Roger Mudd. 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. Famously, yes. famously. Why do you want to be president? Well, I'm, were I to make the announcement and to run, the reasons that I would run is because I have a great belief in this country. 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 run. And I've run. released plans that I want to pass in Congress, like it's passing a renter's deduction so people can deduct their rent from their taxes. I want to make HIV medication free at the point of care. I want to make the child tax credit paid out monthly, not annually, which during COVID cut child poverty in, you know, 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, 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. You know, that I graduated with a JDMBA from a top university. And I went and with that education went and was a top. surrogate volunteer for the Biden campaign traveled to every single swing state in this country. You did volunteer campaign work. Well, yeah, but I think it's, you know, much more significantly than that.

I was, you know, a top surrogate for the campaign that traveled all over and inspired a new generation of Americans to believe in public service and politics. And overnight built a audience of millions of people just using my own two thumbs on my social media and single-handedly inspired them to volunteer. volunteer for and be excited about the party in 2024. And nobody asked me to do that. Nobody showed me their roadmap 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 yourself in the world? Working for and with the John F. Kennedy Library presenting the Profile and Courage Award every single year this year. You presented the award. Yeah. And represent my family in

alongside my mother as ambassadors to Japan. 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 that 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 means that that's not a job. So I think that my experience is exactly what the Democratic Party needs right now from candidates. I'm speaking with Jack Schlossberg, who's running for Congress. We'll continue in a moment. This is the New Yorker Radio Hour. This is the New Yorker Radio Hour. I'm David Remnick. And I've been speaking today with Jack Schlossberg. Schlossberg is a grandson of President Kennedy. And in November, he announced that he'd run for Congress in Manhattan. The incumbent, who's now retiring, is a liberal stalwart named Jerry Nadler, who began serving in Congress in 1992, just a few months before Jack Schlossberg was born.

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 people do care a lot about this issue and they don't even 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. 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 AI, no special interest group money. And I said that at a time when I did not realize my two main opponents, Alex Bores and Michael Lasher, would accept tens of millions of dollars in Super PAC money, tens of millions of dollars from billionaires. Okay, I understand that objection, but they would turn around and say,

but I'm not connected like our opponent. I don't have Bet Midler, Lauren 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, you know, 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. I've accepted contributions on the hard side. That means, you know, if you or anybody, Lauren Michaels, whoever you just referenced,

contributes to our campaign, that's a hard money side 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 to the campaign side. And people don't understand that even though we've outraised them and we've raised $3 million, 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 they regularly spend my opponents in a single day. And it's very important also to remember that Alex Bores is backed by a guy named Chris Larson. Chris Larson 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 Michael Lashers, a super PAC is funded by a billionaire who just spent tens of billions of dollars against...

Who is that? Michael Bloomberg, against Mayor Mondani, trying to defeat the Democratic nominee for mayor in the last election. Michael Bloomberg has also supported plenty of Democrats in terms of funding. True, but I don't think that, you know, 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. Jack, you were ahead in the race by five points. Or like 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 New York Times that, among other things, described your campaign with a lot of reporting, describing disorganization. After that article was published, I think your polls took a big hit. How do you respond to that Times piece? You know, there was one thing that is accurate in that 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 10 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 that I quickly realized was not for me. The people quoted in that article, all of those stories and anecdotes date back to end of November, early December, when I hired a consulting, 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, you know, printed on the front page of the New York Times with a lot of anonymous sources, no accusations of any wrongdoing. You know, 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 one 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 something like that. but certainly a freshman. What would be the absolute top priority that you would be absolutely focused 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 are committed. So you would move to impeach President Trump, for what? For bribery. He's made $4 billion so far this year, him and his family. He has signed contracts and made deals with foreign countries, following after which his

companies, his son's 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. I think all of these things, bribery is specifically listed in the Constitution as a crime, a justifying impeachment. So, you know, 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 other's running. The person leading in the

polls right now, Michael Lashir, he does not think impeachment is worthy of the Democratic Party's time. He thinks it's a futile effort. He thinks it's going to be too hard. I think that's, we have absolutely no choice. Do you think members of Congress should be able to trade stocks? Absolutely not. I think that's a no-brainer. So where are you that Nancy Pelosi is 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. She exists in a system where she did nothing illegal, and I wouldn't trade stocks.

I'd take it upon myself to do that, but I'm not about to sit here in question and dismiss the tactics of the most effective progressive leader of 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. Well, I would not emulate her stock trading myself, and I would not emulate her stock trading myself, and I, I think that that's... 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, which is... 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 you would support

a continuation of 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 overall 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 AOC 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. I oppose the war. And opposing the war means all funding for that war, including sending offensive weapons to Israel,

with whom we are jointly operating in Iran. To 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 warmaking that is going on there. When the U.S. involvement in the region reached a different, fundamentally different threshold level, that is when I decided to say stop sending bombs, stop sending offensive weapons to Israel. I guess when I'm asking you, was President Biden and Kamala Harris too easy?

on Netanyahu when they were in office? I wouldn't go that far. You know, I think that it's always easy to second-guess policy, but, you know, I think, you know, President Biden was a strong, strong supporter of Israel and 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 live. limit the loss of life there than President Trump has. So their record may not be perfect, but that's how I see it. You think history will be kind to President Biden when it comes to Gaza? I don't think history will be kind to the U.S. when it comes to Gaza, but I do think that, you know, 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. And now I think the situation is very different, where I don't think the U.S. should continue supporting offensive weapons to Israel or their settlements in the West Bank, but that we should not abandon our ally full stop, that 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 oppose, I support funding for the Iron Dome. It protects civilians, including 600,000 Americans who live in Israel. You've backed Mayor Mamdani, I think, any 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 Alexander Acacio-Cortez has as well. Do you or do you see yourself as 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 meaningful. 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. Jack Schlossberg. Thank you so much. Thank you. Jack Schlossberg is writing for Congress, and the primary is on June 23rd.

I'm David Remnick. Thanks so much for listening today. See you next time. The New Yorker Radio Hour, is a co-production of WNYC and The New Yorker. Our theme music was composed and performed by Merrill Garbus of Tune Yards, with additional music by Louis Mitchell and Jared Paul. This episode was produced by Max Balton, Adam Howard, David Krasnow,

Jeffrey Masters, Louis Mitchell, Jared Paul, and Ursula Summer. With guidance from Emily Boutin and assistance from Michael May, David Gable, Alex Barish, Victor Gwan, and Alejandra Deccett. The New Yorker Radio Hour is supported in part by the Trurina Endowment Fund.