Jack Schlossberg, the Kennedy Running for Congress in New York

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1:01The 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 Tudors 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.

1:54And you know what that's entailed. Several Kennedy family members have spoken out against RFK'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 Usha 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.

2:36He 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 ago 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.

3:15Jack Schlossberg: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. 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.

3:50Why did you decide to run into the teeth of such grief?

3:56Jack Schlossberg: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 that was what 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 the truth, which was that he had accomplished so much in the first years of his term.

4:31Jack Schlossberg: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. Tell me about that. What did you want to do and what did they want you to do?

5:02Jack Schlossberg: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 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 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.

5:41Jack Schlossberg: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 in an ad campaign or a movie star, but because I was speaking truth to power about our political systems.

6:30Do you think there are things that you did before on TikTok that you wouldn't do now, now that you're wearing a shirt and tie and campaigning? Would you put on a blonde wig and imitate Putin and all the kind of some of the crazier things you did?

6:41Jack Schlossberg: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, you know, it's not like I was making videos that nobody was watching. I was breaking through pretty well. Yeah, you were. And I think advocate, 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.

7:17Jack Schlossberg: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 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 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's history and current policies reflect putting a priority on organized labor and working families.

8:19Jack Schlossberg: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 my age, my first memory is the death of your grandfather. That's a big set of imperatives to carry on your shoulders. So when did this sort of enter your life, that you had this, there was something unusual attached to your future? There is that one moment that sticks out in my life, and it's 10th grade history class.

8:59Jack Schlossberg: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.

9:29Jack Schlossberg: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.

10:12How 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?

10:27Jack Schlossberg:I've loved politics since I can remember, and I feel motivated by the call to answer. 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 granduncle and godfather, the late Ted Kennedy, once ran for president, and he faced a correspondent named Roger Mudd.

11:06He 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. That's right. Famously, yes. Famously. Why do you want to be president?

11:21Jack Schlossberg:Well, I'm...

11:26Jack Schlossberg: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 of 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 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 to historic lows.

12:06But 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?

12:30Jack Schlossberg:Yeah, absolutely. Why do you deserve this seat? Well, I think my experience is why people are so excited about our campaign. You know, I graduated with a JD MBA 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.

13:02Jack Schlossberg: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 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.

13:40You presented the award. Yeah, and represent my family alongside my mother as ambassador to Japan.

13:49Jack Schlossberg: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.

14:30I'm speaking with Jack Schlossberg, who's running for Congress. We'll continue in a moment. This is the New Yorker Radio Hour.

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17:47This 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 and politics is a very important issue to you.

18:19Jack Schlossberg:I think it's the single most important issue facing our country and our party. And I think 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.

18:52Jack Schlossberg:And I said that at a time when I did not realize my two main opponents, Alex Oras 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. And 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, you know, we need to explain this to people so they understand.

19:25Jack Schlossberg: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, Lorne 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.

20:15And I just – it's very important also to remember that Alex Boras is backed by a guy named Chris Larson.

20:22Jack Schlossberg: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 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 Momdani 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 that, you know, it's not really, 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.