Jack Schlossberg’s Congressional Run

Summary

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United States of Kennedy

Episode Title: Jack Schlossberg’s Congressional Run
Date: December 1, 2025
Hosts: George Civeris, Julia Claire
Guest: Kara Vogt (Washington Post political features writer)

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Episode Overview

Theme:
This episode explores the recent announcement that Jack Schlossberg, the only grandson of JFK, is running for Congress in New York’s 12th district. George, Julia, and special guest Kara Vogt dive into Schlossberg’s eccentric public persona, the tension between legacy and individuality, and what his run says about both dynastic politics and modern political media.

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Key Discussion Points and Insights

1. The Big News: Jack Schlossberg’s Congressional Campaign

[02:56]

• Schlossberg is among over ten candidates vying to replace Jerry Nadler in NY-12, a wealthy, Democratic stronghold.
• The district offers “immediate access to the city’s concentration of wealthy donors, media giants, and Democratic top brass” (Julia quoting The New York Times).

2. Jack Schlossberg: Kennedy Scion Turned Viral Curiosity

[03:31] – [04:20]

• Known for social media antics: shirtless singing/dancing videos, online spats with cousin RFK Jr., provocative tweets.
• Has described wilder behavior as a “strategic ploy to get people talking about politics and reclaim the attention economy.”
  • “He once, of course, tweeted to his followers asking if Usha Vance is hot [referring to J.D. Vance’s wife].” — George [03:58]

3. Kara Vogt’s Reporting: Portrait of a "Silly Goose"

[04:58] – [11:21]

• Kara details her year-long attempt to profile Schlossberg, including personal family challenges (sister Tatiana’s cancer diagnosis).
• Unpacks his blend of tradition (Profiles in Courage Awards, “putting on a suit and talking about his grandpa”) with performative, sometimes trollish online bits.
• “I feel like I got the bit… he was lending this political heritage, this really American idealism… to this new way of doing politics.” — Kara [05:34]
• Kara notes that Schlossberg embraced her offhand description, calling himself a “silly goose” in public—a phrase she coined in their chats.
  • “Everywhere I go, I see Jack calling himself a silly goose.” — Kara [10:18]

4. Navigating the Kennedy Legacy

[11:21] – [12:39]

• The “tension” of living up to both the Kennedy myth and his own identity: earnest one moment, provocateur the next.
  • “He both tries to live up to it sometimes and doesn’t at others.” — George [11:30]

5. Social Media Star to Candidate: What Changes?

[12:39] – [14:06], [17:49] – [22:10]

• After early forays as a surf-shop employee and viral actor, Schlossberg tried “to formalize whatever that organic energy is,” launching a YouTube show and now his campaign.
  • “He was gonna be an actor, he was gonna practice law, he was gonna work for the Biden campaign. The jobs… it’s almost like when you ask a 5-year-old what they want to be when they grow up. It was all very like, anything, anything.” — Kara [12:54]
• Since announcing, he’s scrubbed his social media: YouTube show unlisted, tweets (including infamously off-color ones like “Pod Save my limp dick” [21:29]) deleted.
• Discussed whether this “cleanup” is a mistake, possibly removing what made him appealing: authentic, goofy, a digital native unafraid to be weird.
  • “What he is doing is not why he resonated with people in the first place. Yeah. Like, I feel that in my bones.” — Kara [22:04]
  • “Anyone who works in oppositional research has already gotten all these tweets… so it’s not like… they just get the entire ream of any filthy thing he ever said.” — Kara [24:19]
  • “To even think this could make a difference makes me think he’s working with someone who doesn’t quite know how the media ecosystem works.” — George [24:30]

6. Campaign Messaging: Platitudes over Policy

[25:41] – [29:40]

• Hosts review Schlossberg’s campaign website: imagery echoing JFK and JFK Jr., list of vague “12 Promises” (e.g., “courage,” “positivity,” “accountability”) without concrete policy.
  • “They almost strike you as something you would find on bad art at home goods.” — Julia [27:13]
  • “It kind of strikes me as someone who doesn’t quite know who he is yet, but also someone who much has been asked of him, specifically from the Democratic establishment.” — Julia [29:40]
• Kara notes he’s “really earnest… even though he is funny, there is an earnestness in his humor. He is never actually totally detached.”

7. Within the Democratic Establishment: Symbol or Change Agent?

[29:40] – [32:37]

• Schlossberg was asked to speak at the 2024 DNC, consciously grouped with Jimmy Carter’s grandson to present a “blessing” from Democratic dynasties.
• His actual campaign and online persona clash with the symbolic expectations placed on him by party leaders.
  • “He didn’t talk about what the party could be doing reaching out to young people… He was talking about his grandparents and he talks about his mother. And I think to the Democratic Party he is still that. He is above all else a Kennedy who can remind Democrats of the good times.” — Kara [30:28]

8. Public Perception: The Internet “Ick” and Dynastic Fatigue

[37:48] – [43:31]

• Despite internet virality, his campaign announcement was widely met with skepticism and even derision, largely due to dynastic fatigue and tough competition.
  • “Despite all the love he has experienced over the last two years, when he did finally announce his run, the reaction that I saw at least was mostly negative.” — George [37:48]
  • “People of both genders… were like, what if we kiss under the ball drop? To being like, ew. Ew. I’m just so sick of seeing Jack Schlossberg. He’s giving me the ick.” — Kara [40:54]
• Discussion of a shifting generational mood: voters (especially younger ones) are less jazzed about “legacy” candidates, especially with the current association of another Kennedy (RFK Jr.) as a problematic public figure.
  • “It seems that there is really not an appetite right now for dynastic politics, at least maybe not in his district, honestly…” — Julia [41:42]

9. The Burden of Legacy: What Can Modern Kennedys Be?

[43:31] – [45:37]

• Drawing parallels to the Bush family and the British royal family, the hosts and Kara debate whether it’s possible for dynastic heirs to find authentic roles outside politics.
  • “If you’re going into politics, there is a thought and expectation about who you are and what you represent… It is impossible to figure out who you are without that history weighing on you.” — Kara [43:31]
  • “Honestly, I could see someone like Jack being equally as successful in a similar role [as Jenna Bush] in a non political, but still entertainment, still a very visible legacy of this family.” — Julia [45:06]
  • Kara: “There is a way of being able to translate the life experience and the people, you know, for the rest of us. That I think is one of the most compelling ways to be a Kennedy right now.” [45:20]

10. The Camelot Paradox: Kennedys & Media Attention

[45:50] – [47:47]

• Reflection on why the Kennedys both court and spurn the press—how sustaining the family myth depends on a delicate dance with public attention.
  • “Their power is only really derived from public attention. And yet to lend oneself publicly… is also to lose the really humanity of being a private citizen…” — Kara [46:20]
  • “It feels to me, it’s a two way street… there are at least some members of the family who aren’t ready to give up on being this important family for America.” — Kara [47:11]

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Notable Quotes & Memorable Moments

• On Jack’s Self-Awareness:
  “He was like, oh, that’s really — that’s a good way to think about it. I hadn’t thought about myself that way.” — Kara on Jack adopting the “silly goose” label [10:18]

• On the Campaign’s Tone:
  “They almost strike you as something you would find on bad art at home goods.” — Julia, on the 12 Promises [27:13]

• On Gen X and Kennedy Nostalgia:
  “John Jr. was going to be the last great hope, I think, and maybe would have been that person for Gen X had he not reached his untimely end.” — Julia [42:57]

• On Media and Myth:
  "Their power is only really derived from public attention. And yet to lend oneself publicly ... is also to lose the really humanity of being a private citizen..." — Kara [46:20]

• On Dynastic Fatigue:
  “It seems that there is really not an appetite right now for dynastic politics…” — Julia [41:42]

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Important Segment Timestamps

• Announcement & Race Overview: [02:56] – [03:31]
• The “Silly Goose” Persona Origin Story: [04:58] – [10:18]
• Kennedy Traditions vs. Modern Tactics: [11:21] – [12:39]
• Social Media to Seriousness—The Campaign Pivot: [17:49] – [22:10]
• Website and Campaign Platform Review: [25:41] – [29:40]
• Democratic Party Perceptions: [29:40] – [32:37]
• Public and Internet Reaction: [37:48] – [43:31]
• The Burden and Paradox of Kennedy Legacy: [43:31] – [47:47]

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Conclusion

The episode threads together the complexities of Jack Schlossberg’s identity as a Kennedy, a viral internet figure, and now, a congressional candidate. The hosts and Kara Vogt share skepticism about the wisdom of Jack’s shifting persona—questioning whether discarding his wild authenticity for platitudes will resonate with voters or merely underscore the tensions inherent in American dynastic politics. Ultimately, Schlossberg’s run serves as a microcosm for the enduring allure and awkwardness of the Kennedy legacy in an era increasingly skeptical of inherited power.

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Transcript

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[George Taveras]

I'm George Severis.

[Julia Claire]

And I'm Julia Claire, and this is.

[George Taveras]

United States of Kennedy, a podcast about our cultural fascination with the Kennedy dynasty. Every Week, we go into one aspect of the Kennedy story. And today we are taking a little break from our regularly scheduled programming to talk about something that's been in the news lately that is right up our alley.

[Julia Claire]

And no, we're not talking about RFK jr. S erotic poetry or his recent decision to change the CDC website's language on vaccines and autism.

[George Taveras]

We are talking about something a little less alarming than that, which is that one of our favorite characters here on United States of Kennedy church, Jack Schlossberg, JFK's only grandson, has announced that he is running for Congress in New York.

[Julia Claire]

Schlossberg is one of over 10 people currently running to replace Jerry Nadler in New York's 12th congressional district. This is the wealthiest district in New York and a huge Democratic stronghold. According to the New York Times, quote, it offers immediate access to the city's concentration of wealthy donors, media giants, and Democratic top brass.

[George Taveras]

So we've talked about Schlossberg before on the podcast, mostly as a sort of confounding curiosity. This very strange, very 2024, 2025 social media star. So he's posting shirtless videos of himself singing and dancing. Then he's starting fights with his cousin, RFK Jr. He is talking about how the Democratic Party needs to move on from old men, and he's endorsing Zoran Mamdani in the New York mayoral election. And then there's the sort of more trollish part of him. He once, of course, tweeted to his followers asking if Usha Vance is hot. His own grandmother, Jacqueline Kennedy. And when he's confronted about this behavior, he claims that it is all a strategic ploy to get people talking about politics and reclaim the attention economy from the Republicans.

[Julia Claire]

I mean, clearly he's a genius. But today we wanted to talk more specifically about his foray into electoral politics and what the race might look like for him. To do that, we are joined by Washington Post political features writer Kara Vogt.

[George Taveras]

Okay. Hello, Kara. So let's get into it. Almost exactly a year ago today, you wrote this big piece in the Washington Post on Jack Schlossberg titled We don't know Jack, and I want to know what led to that piece and what the experience of trying to chase him down was like.

[Kara Vogt]

Thank you for asking. As I write in the piece, I encountered Jack the way I'm sure all of you did, which is on the Internet. And I can't remember exactly what led me to it, but I think it was the videos of him doing the various impressions of New Yorkers who do not want to vote for Robert F. Kennedy, Jr. For president. This was back in. I think it was April or May. Yes.

[George Taveras]

And there were a lot of accents, from what I remember, that some people took issue with. You know, Julia and I, in past lives were comedians. So we are obviously very well versed in sort of character work, and we really appreciate the intent.

[Kara Vogt]

Right. There was definitely some blowback. I think the New York Times headline on him doing that was like, offensive accents from the Kennedy scion, which was funny to me because they totally missed the point. But I will also say that missing the point was why I was so intrigued by Jack, because I feel like I got the bit. I feel like I understood what he was doing, that he was lending this political heritage, this really American idealism that anyone who knows the Kennedys has come to admire, lending it to this new way of doing politics. And I thought, holy shit, this kid is doing something fascinating. And I thought it was funny, too, because he was still doing all the very traditional Kennedy things of going to the Profile and Courage Awards and shaking hands and putting on a suit and talking about his grandpa. So I reached out to him on Instagram and I asked him for his email address, and he gave it to me, and we started a correspondence of, I'd like to write about you. I'm sure I'm not the only one. And we kept setting dates to get together to talk. And actually, I can talk about this now because I'm sure listeners of this show will have seen the news that his sister, Tatiana Schlossberg, has terminal cancer. Right about a month after Jack and I first started talking. We had set a date to get together for early June for this profile that I was going to write about him. And he said to me, I'm so sorry, My sister has just had a baby, and we think there's also cancer. And I was like, oh, my goodness. Wow. And I said, well, okay, totally. Please take time you need for your family. And as Tatiana writes in the piece, again, I don't feel badly disclosing this now because I think that this is all sort of in the open. She's really been on a roller coaster of, she's better. She's not doing better. She's better. For most of 2024, at least. The times when Jack and I were talking a lot, she seems like there was a good sense that she was on her way to remission and was going to be okay. But anyways, we had a false start there, and we got together. I happened to be in New York at the end of June. We took a long walk together in Chelsea, where Jack lived and talked about his family, about the campaign, about. This was the weekend after the debate between Joe Biden and Donald Trump. So everyone's like, what's going on?

[George Taveras]

Right.

[Kara Vogt]

He was himself trying to figure things out. He just signed this contract with Vogue. He didn't know what the Vogue thing was going to be, but he's like, you know, I think things are better. Like, we should do the profile sometime this summer. And I said, great. And then the can just kept getting kicked down the road for various reasons of busy or not a good time. I detailed all of that in the story I wrote about him. And our plan had always been to go paddleboarding, and that's one of Jack's favorite activities. And when I said, let's do something around the Chicago convention, the Democrats were there to coordinate. Kamala Harris. He said, great. And this is very funny. The kinds of things you do as a journalist are not so dissimilar from the kinds of things you do on a date or when you're, like, getting ready to meet up with somebody. Like, you pick out, what are you going to wear? How are you going to bring all the tools you need for the job without seeming really weird? Our job is so weird. We're, like, really invasive, and we're doing these weird things with people, these stunts. So I had ordered a very special waterproof case for my phone that would still allow me to use a microphone. So while we were out paddleboarding, I would have what I needed. But of course, we never went paddleboarding. He blew me off, and he just was like, now's not a good time. I'm the only person here representing my family at the dnc. It's not a good time. And I was, at this point, we'd pushed it three or four times. So speaking for myself, I was really mad. Said, such is life. Such is life. And then when all of these Jack Schlossberg lookalike contests started showing up last November about a year ago, I said to my editor at the time, I am the world's foremost expert on John Bovier Kennedy Schlossberg. And I am feeling crazy seeing all of these various things exploding, all of the interest in him hitting this, like, fever pitch. And at the time, Jack and I weren't talking that much, but he was still very much in the way that we all surveil each other. He's still looking at my Instagram stories, and he's looking at what I'm doing and something I should have said at the beginning. Full disclaimer. We all know I. The term silly goose has been our lexicon for a long time. But when Jack and I first started talking, when I was trying to pitch him on the kind of story I would do, I said, you know, you're like a silly goose. Like a silly goose who's, like, trying to get the truth out there. And he was like, oh, that's really. That's a good way to think about it. I hadn't thought about myself that way.

[Julia Claire]

Then.

[Kara Vogt]

Everywhere I go, I see Jack calling himself a silly goose. And this happens all the time. Maureen Dowd, who just wrote the wonderful profile of Jack for the New York Times, I happen to know that she had called Dick Cheney Darth Vader, and it became a name he liked so much that he stuck with it. And she said to me, like, yeah, take it as a term of endearment or as a sign of you doing good work. That someone. You say something to someone as a writer, and they want to make it their own thing. Long story short, I used the arc of Jack to tell the story of Jack and what he's like and trying to give a sense of not only his energy, his Persona, what he was doing as this online influencer for the Democrats, but then also a sense of what it's like to be a Kennedy, which I feel like with him, I got a good glimpse, which is enough attention to know and to have an impact, but not so much that there's scrutiny and not so much that there's pressure and the very weird extended family. I feel like I got a little glimpse into that, too, that there's an expectation that because you're related to someone who has a Kennedy last name, that you will behave a certain way. You have a certain duty.

[George Taveras]

Right.

[Kara Vogt]

I feel like Jack really thinks that tension, that kind of expectation that we put on Kennedys, I feel like he felt that very much.

[George Taveras]

Yeah, well, he both tries to live up to it sometimes and doesn't at others. I mean, the tension you're describing is him being a silly goose, as you say, in the sense that he is posting crazy things online, whether it's shirtless videos of himself dancing or really provocative Twitter jokes or whatever. So he's doing that on the one side, and then he's also interviewing Mike Pence and giving him the Profile Encourage Award on the other. So it's interesting now, seeing him run for Congress, you're sort of like, so, which one of the two won over on the one hand, the Kennedy side did because he's going into electoral politics, which he feels is his birthright. On the other hand, what set him apart is the sort of crazy, crazy social media star thing. And so if he abandons that, then he only has the Kennedy name to trade in on. But since writing this piece, how has he changed? Would you describe him differently now in the years since then? Obviously, Donald Trump was eventually elected after Jack was like, very focused on being a mouthpiece for the DNC and going on Jimmy Kimmel and speaking at the DNC and whatever. How has he evolved over the last year?

[Kara Vogt]

So I'm gonna bring in some of the reporting from Maureen Dowd's profile and fill it in with some of my own knowledge. So about a year and a half ago, last spring, Jack was living in Hawaii, working in a surf shop. He did not have a plan, he did not know what he was going to do. And the videos were pretty organic and silly and they took off. It was the right content for the right time in a moment of politics that felt so icky and weird. And here's this symbol of Americana helping us feel a little less icky and weird about all of it. He was gonna be an actor, he was gonna practice law, he was gonna work for the Biden campaign. I mean, the jobs that Maureen mentions in that piece, it's almost like when you ask a 5 year old what they wanna be when they grow up. It was all very like, anything, anything. And I don't have inside knowledge into this, but what I've seen from Jacques over the last 18 months, two years, is an attempt to formalize whatever that organic energy is, an attempt to put it into something like a YouTube show and now like a run for Congress. I do believe that he very much embodies the sense of, you know, to quote his grandfather, what can you do for your country? I just really botched that on a Kennedy podcast. I'm really sorry.

[Julia Claire]

Wait, it's ask not what your country can do for you. Ask what you can do for your.

[George Taveras]

Country you can do for your country. I have to say, I've always thought that is such a crazy thing to say in an inauguration speech when you're trying to prove what you are offering to the people, to be like, okay, thank you for electing me. And now the ball's in your court, folks. Like, it really has always struck me as so strange.

[Julia Claire]

We'll be back with more United States of Kennedy after this break.

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[Julia Claire]

And we're back with more United States of Kennedy.

[George Taveras]

One of the reasons why I'm asking about the YouTube show is because we noticed that it's one of the many things that has now been scrapped from the Internet. So if you go on the YouTube page, it says all 10 episodes are unlisted, which means, I believe that if you have the link, you can watch them. They're not like deleted.

[Kara Vogt]

But they're not publicly available.

[George Taveras]

But they're not publicly available. Yeah. So yes. And the YouTube show, for anyone who doesn't know he was in a van and doing a combination of like speaking directly to camera and also interviewing guests.

[Kara Vogt]

Right. And I think it was mostly the camera stuff. I didn't catch every episode. I did watch the Schumer episode because I was like, what are we doing here? The show did not take off. I think that he has much more of an audience when he is just kind of reacting spontaneously. And I also think that there's a lot of people with shows, there's a lot of influencers who have a YouTube show. He is not special and he's late to the game in that regard. And now we're seeing in his congressional run, that's an attempt to formalize some of that joie de vive too, of like trying to fit it into the strictures of running for office. And you have to wonder what his campaign would look like if he was not a Kennedy, because plenty of influencers run for office. I'm forgetting her name. There was a young woman in Arizona who just ran in the special election. Who is that? She's a Democratic influencer.

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[George Taveras]

Deja Fox.

[Kara Vogt]

Yes. Great. Very big deal. Gen Z. Democratic influencer. And they're not really bound by the should I go to shake hands at the soup kitchen Energy. I haven't kept up with what Jack's stops have been so far about organizing and that kind of thing. But there's a real old school energy that feels like it's on his campaign. And I have to wonder how much of that is just that's the way Jack wants it and how much of that is. There's an expectation that he would have a more traditional campaign in some respects. And also, do I see it that way because of the way that we all view Kennedys. Kind of novel and new and interesting, but we always have this lens on him because of where he came from and what past generations did. Kennedy's are a Rorschach test. Right? The way that we see them tells us as much about us as it does about.

[George Taveras]

Yeah, totally.

[Kara Vogt]

Right.

[Julia Claire]

And I think when he first came into the public consciousness, it was through these very silly videos. And I think that did butt up against a lot of our views of what a Kennedy is or what a Kennedy is, quote, unquote, supposed to be. And now his campaign is like a push and pull between those two almost opposing forces. Because the reason why he has become notable and popular is because of this goofiness, this silliness, these kind of irreverent social media posts. But now that he is running for a congressional seat, it seems like he is either himself or he is being advised to pull back and distance himself from that. What has made him prominent.

[George Taveras]

Right. That's what seems confusing to me because we watched and listened to some interviews with him last time we talked about him on a broader level. If he. Months ago he did this interview with Jen Psaki, he went on Kimmel. And his value proposition has always been, I am being intentionally provocative in order to gain the attention economy the same way Republicans do because Democrats are too scared to be controversial and provocative. But if we game the attention economy, get eyeballs and ears on our side, then we can use that attention power to talk about the real issues. And you even said it like, he's a silly goose and he's out there to spread the truth or whatever. And I really have noticed that since announcing the congressional run, he hid his YouTube series. He has deleted certain tweets. Julia, what was the one you found?

[Julia Claire]

Oh, the one immediately after the 2024 election where some of Harris staffers went on Pod Save America and the tweet said, I think Pod save my limp dick.

[George Taveras]

Right. So that's gone now.

[Julia Claire]

So that's gone now.

[Kara Vogt]

Oh, I should check my profile for broken links. I think I mentioned that one at length. Yeah, yeah.

[George Taveras]

I remember last time we were talking about him, I looked through his Twitt to be like, what are his craziest recent tweets? And it was like, I would scroll for, you know, 15 minutes, and it would still be like, a week ago. I did the same thing today. And he barely tweets anymore. And when he does, it's very serious. So I don't know. What. Do you think this makes sense as a strategy? Isn't he sort of abandoning what drew people to him?

[Kara Vogt]

So I have a rule for myself because I live in Washington and I work for the Washington Post, that I do not go too deep on New York politics because it's a city that is so full of so many political reporters with way too much time on their hands. So I cannot speak to the particulars of the New York 12. What I can say is what he is doing is not why he resonated with people in the first place. Yeah. Like, I feel that in my bones. And I don't know if it's a good political strategy. I have no idea what these voters are like. It is interesting to me, though, in a moment when so much of the discourse in politics is about authenticity. You know, I'm thinking about not to, like, compare him to Graham Platner, the Senate candidate who's running in Maine, who, in case your listeners are not caught up, Democrat, progressive, but likes hunting and is an oyster farmer and has this kind of hipster energy to him, like sort of Noah Khan core. And he has this tattoo from when he was in the armed services that, it turns out, was a Nazi symbol. And he got it covered up recently once the symbolism of the tattoo was known. And I'm bringing this up because there's a way in which really leaning into who you are and your story and where you've been without shame is really powerful for a lot of people. There's a lot of people in this world who have made a lot of mistakes and said things they wish they hadn't said and posted things they wish they hadn't posted and have talked about, you know, learn my lesson, or, yeah, that was weird. Or even just owned it and been like, you know what? At the time, POD should save my limp dick. You know, like, for example. And I feel like what made Jack powerful last year and what made him so interesting is that because of who he was, there were things that he could get away with and things that were funny and things that made sense. If they came out of anybody else's mouth or were on anyone else's feed, you would be like, what? Like, I can't even imagine most other interesting Democratic influencers saying, pod, save my limp dick, and having it have that effect. And I, I would be curious what this campaign would have looked like if he just left everything up there and the oppo people went through. And also, it's very silly because, like, anyone who works in oppositional research has already gotten all these tweets because they know how this works, and there's ways to recover them very easily. So it's not like if an enterprising reporter wasn't asking around, they just get the entire ream of any filthy thing he ever said. Right.

[George Taveras]

If anything, that's what makes me think it is a incorrect strategy. Not because he's, like, trying to be respectable. Like, I get trying to be respectable. To even think this could make a difference makes me think he's working with someone who doesn't quite know how the media ecosystem works.

[Julia Claire]

Yeah, I, I think also, you know, we just, obviously in New York, we just had the mayoral race, and Zoran is someone who's also a digital native, a social media native, and he just left all of his tweets up, which I think makes sense.

[Kara Vogt]

And those music videos.

[Julia Claire]

Right. And he kind of made it part of his campaign. And like, oh, look at me. I was so silly. And to your point about Graham Platner, a lot of his posts, you know, opposition research has uncovered some Reddit posts of his, and he has also folded that into his story, saying, I was a lost young man, as so many American men are. And I, you know, I have since learned and educated myself and changed. And there's something powerful, there is something that resonates with people. And I'm confused about Jack's decision to distance himself from the very thing that endeared him to people.

[George Taveras]

Yeah. You know, we wanted to sort of take some time to go through his campaign website and more specifically, you know. Okay, so how is he selling himself now? This is like his. This is almost like a big reset for, let's say two years. All the media coverage of him was like, look at this strange curiosity. You'll never believe this. He's a Kennedy, but he's shirtless and he's hot and he, like, has a funny good relationship with his parents, and they're sometimes in his videos. But then he also can dress up and suddenly he's covered like an influencer. And then suddenly it's this very old fashioned. First of all, the imagery, Julia pointed this out to me earlier, the imagery really, like references a bunch of old Kennedy.

[Kara Vogt]

Yes.

[George Taveras]

Images. Whether that's his grandfather or whether that's JFK Jr and then we have 12 promises to the people of New York's 12th district and it's these really like platitude ridden sentences for each one.

[Kara Vogt]

Also not for nothing, but like I just googled Jack Schlossberg to pull this website up and it wasn't even the first five pages of results I had to actually put in Jack Schlossberg campaign to get it it. So that doesn't SEO.

[Julia Claire]

So the 12th promises to the people of New York's 12th district, service, courage, strength, accountability, optimism, independence, focus, pragmatism, unity, patriotism, creativity and positivity. I mean they almost strike you as something you would find on bad art at home goods.

[George Taveras]

Yeah, well, and also each of them is truly written as like a thesis statement in a high school essay or something. It really is very much like Gandhi.

[Julia Claire]

Once said, like under, under focus it says all three branches of government are equal, but Congress comes first. Just check the Constitution. It's article one for a reason. People's House has all the power.

[George Taveras]

I do want to say in his defense, you know, it's important to remember and I know we don't want to talk about the ins and outs of New York politics. It's important to remember he is running for New York's 12th Congress congressional district, which is if you're thinking of like the most stereotypical rich, out of touch, vote blue, no matter who Democrats that will respond even to this day to like, we gotta get that Cheeto out of the White House like this, this is that district.

[Kara Vogt]

Yes.

[George Taveras]

So yes, it might seem completely beside the point to us and we might think it sounds like lame or something, but these are exactly the kind of people who would respond to this kind of messaging. So that would be my one point in his defense.

[Kara Vogt]

I also think that one of the through lines of Jack from the time when he and I first started talking to now is he's really earnest. And even though he is funny, there is an earnestness in his humor. He is never actually totally detached. There isn't a wryness, there isn't a cynicism. It's silly, it's ridiculous, over the top, but it's always earnest. And Julia, as you were reading those qualities aloud in some of the descriptions, what's funny is the intonation of it is still very Jack. Like in that he has a kind of Peter Pan ish quality to him that is part of the charm a little bit like, I'm not gonna be weighed down by my three and a half decades of living in America in a mostly post 911 world. I am going to still see the good qualities. And there's a bit of a wink and a nod to me as I hear you read through them, that if you know Jack and you're familiar with his game, you can kind of see the sort of intent behind the earnestness. And I guess to the point George was just making about the voters, if you don't know it, it just sounds like a nice young boy whose grandfather was their favorite president, and they will go out and vote for him. So maybe he's trying to kind of have it both ways. I don't know if it'll be effective for voters, but I could see it that way, that he's not being dishonest and, like, totally burying who he was, but he's playing up the very particular aspect of his earnest self to various audiences and seeing how the chips fall.

[Julia Claire]

I mean, he's also not making any specific policy promises. It's all these, as George said, vague platitudes. So I don't know. It's interesting. It kind of strikes me as someone who doesn't quite know who he is yet, but also someone who much has been asked of him, specifically from the Democratic establishment. You know, as you noted in your piece, in 2024, he was named a New York delegate at the DNC, and then he was a speaker at the DNC in Chicago. But then in the aftermath of Kamala's loss, he was very critical of Kamala's campaign. You know, rightfully so. Sure. But I'm confused about this push and pull with him. Like, do you have a sense of how he is perceived within the Democratic Party?

[Kara Vogt]

I think it was telling that Jack was asked to speak. And to be clear, like, this convention came together very quickly. Right. It wasn't like, oh, we know exactly what's gonna happen, because Kamala Harris became the nomin a couple weeks before. So a lot of seat of the pants stuff. I know that his addition was a little bit on the later side, and it was telling, I think, that they had him show up with Jimmy Carter's grandson. Remember that? It was an early block. I forgot what day of the week it is. Was not during the prime time. So this was really fan service for the people in the convention center. And it was getting the blessing of the Kennedy family and the blessing of the Carter family. And that was important in a moment when RFK Jr is still looming as this free radical. He hadn't quite linked arms with Trump yet. I think that was coming in, like, the week or so later. And that's what he talked about. At the dnc. He talked about the legacy, he talked about the baton. He didn't talk about himself. He didn't talk about his videos. He didn't talk about what the party could be doing reaching out to young people who the likes of whom follow him. He was talking about his grandparents and he talks about his mother. And I think to the Democratic Party he is still that. He is above all else a Kennedy who can remind Democrats of the good times.

[George Taveras]

It's also like because RFK Jr. Especially now, obviously is inside the Trump administration, which he wasn't then. There is almost, I would imagine in the Democrats mind this idea of they have the bad Kennedy and we have the good Kennedy. Look, they have the one who's spreading misinformation and having affairs with journalists and then we have the one who's young and attractive and has hope in his eyes and you know, is in inspiring the youth.

[Kara Vogt]

Yeah, I think that's probably right. But I think it's telling because I don't think the value they saw in him is really through the things that connected so many people to him, which is his social media talents and his like just attention talent. And that's what he talked to Jen Psaki about. And in other interviews he's discussed this. There's a real disconnect between the value that Jack can add to Democrats and the value they want him to add. At least historically speaking. The run for Congress is like a whole other thing.

[Julia Claire]

Right. Right.

[George Taveras]

We're going to take a short break. Stay with us.

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[George Taveras]

And we're back with United States of Kennedy.

[Julia Claire]

Well, it seems like the value that perhaps he has to the Democratic Party. How they see him is symbolic. And I'm curious if you have a sense of how he sees himself in that way. And how do you think he sees his own role inside or outside of the Democratic establishment?

[Kara Vogt]

So Jack and I have never spoken on the record, so I want to just premise what I'm about to say that way, because I'm not at liberty to share what's in his head. But I think you see this play out on social media. I think you see it play out before he started cleaning up his various feeds. I think there's a real tension of being yanked in the direction of like, okay, it's your turn, kid. We need you to come do this thing. And just like your sisters and your mother before you, it's your turn to carry the mantle for us. And I think he does have really strong ideas about the fact that the party is not doing what it can to attract new audiences, to bring people into the fold. I think his criticism of the campaign after the fact was the most telling aspect of this.

[George Taveras]

And his endorsement of Zoran, you could say, like he felt very passionate about, you know, he has this famous video where he's like, we need to get all these old Democrats out of office. We need young blood, blah, blah. Julie and I were talking about this off mic earlier and she made the point that he both represents the establishment and not the establishment. Like, in his mind, he doesn't shy away from the Kennedy name. Like, it's very open. It's on his website. Like, he both, both thinks part of the value proposition is that he is a quintessential Democratic candidate from the old times. And also that he's part of a new generation that is unseating the old crusty men.

[Kara Vogt]

Right. And I think that as we've been discussing, though, it doesn't work so seamlessly as him being able to do both things. In fact, both things are often at odds with each other in how they manifest in him.

[George Taveras]

Yeah. And so we've talked about, you know, how he's perceived within the Democratic Party, how he perceives himself. I mean, the obvious next question is how. How actual normal people perceive him. Because I have to say I was not surprised, but I was intrigued by the fact that despite all the love he has experienced over the last two years, when he did finally announce his run, the reaction that I saw at least was mostly negative. All these people that thought he was so fun and funny and shared his videos were not being like, all right, I'm pumped up, let's go. I think part of that is because it's such a crowded field. And I was just saying before, like, he's not even in this field. The young and hot one. There's literally like a 25 year old former Parkland teen who's cool and gay and going around and giving, like, fun interviews, which really sucks for him. He can't even be, like, the infant terrible of this specific campaign.

[Kara Vogt]

Totally.

[George Taveras]

What is your take on the response? I mean, it sort of landed with a thud to me.

[Kara Vogt]

Yeah, I think there's a couple things going on. One of them is, for sure, this is a really crowded race full of charismatic, gay, beautiful men.

[George Taveras]

Exactly.

[Kara Vogt]

Yeah. But, like, also maybe George Conway. Kellyanne Conway. It is a clown car of people running.

[EF Ultimate Break Announcer]

Yeah.

[George Taveras]

And there's also, like, in the more serious side, there's, you know, Michael Asher is, like, Jerry Nadler's protege, and Nadler will probably endorse him. Like, there's already a candidate for the serious older people. There's already a candidate for the, like, young, progressive people. There's very little to grasp onto.

[Kara Vogt]

But the comparison point and the scene setting here is important because you can imagine in another race where it's just. I don't know. Just for example, let's say Jack and Dan Goldman, the kind of older. I forget which district he represents. Forgive me, New Yorkers.

[George Taveras]

It's my district.

[Julia Claire]

Of course it's ours.

[George Taveras]

Yeah, it's ours. It's ours.

[Kara Vogt]

Okay, great. So he is very serious and a little bit older and not a good hang and, like, very establishment coded. And you could see, like, someone like Jack running against him and just kind of dancing circles around him, being like, look at me. He can't do that in this race. So his fish tank is. He's a little bit boxed in by the other fish that are already there. I don't know why I'm talking about fish. Just please bear with me. It's a tablet. Well, the other thing is, I do think that for whatever reason, there are some people who are getting the ick out there. I think that Jack's popularity really was peak pre to post election. And in fact, pre2024 election, when he was starting to do more events with Pennsylvania Governor Josh Shapiro and Michigan Governor Gretchen Whitmer. You could kind of see this, like, strain of, like, he's trying to make these guys a little cool, like, make it kind of get people excited about the. I felt like that was some of his weakest content that he was making. And after the election, he exploded with his, like, tear it all down energy. And then with the show, I hear more people who last summer were saying, oh, my God, Carol, he's gonna be at the convention. What if we kiss under the balloon drop? Just, like, fantasizing about, like, what it would be like to meet Jack Schlossner.

[Julia Claire]

I mean, they were calling him the Internet's baby girl, right?

[Kara Vogt]

Very baby girl. People of both genders, I should say, were, like, reaching out to me. All sexual orientations were like, what if we kiss under the ball drop? To being like, ew, Ew. I'm just so sick of seeing Jack Schlossberg. He's giving me the ick. I don't know what makes the Internet turn on somebody like that. I can't figure it out. I would be curious if you guys have any thoughts on why that is, but it is definitely happening.

[Julia Claire]

I have a theory in this particular political moment. It's interesting because Jack, as we said, he endorsed Zoron. In Zoran's victory speech, he specifically referenced that his election is the end of a political dynasty. It is the end of the Cuomo dynasty, and it is implicitly or explicitly, hopefully, the end of dynastic politics in America.

[Kara Vogt]

And crucially, a Cuomo dynasty is, in part a Kennedy dynasty, given the marriages.

[Julia Claire]

Right. I can see why people like Jack Schlossberg as a fun, kooky, almost like a little Edie, deeply little Ed coded for the modern age. But it seems that there is really not an appetite right now for dynastic politics, at least maybe not in his district, honestly, because his district went for Cuomo. So maybe there is more of an appetite in his district for a member of a political dynasty. But I think it's both the fact that we are sick of dynastic politics writ large in this country and also that the other most prominent Kennedy right now is. Is anathema to anyone left of center.

[Kara Vogt]

That's my theory.

[George Taveras]

Right. And the fact that Jack has obviously spent so much of his time arguing with the Kennedy you're referring to, RFK Jr. Is not quite having the intended effect. It's like the Kennedy name has still taken a hit because of, you know, the last two years.

[Julia Claire]

Definitely.

[George Taveras]

And to be honest, the last generation that really associated the Kennedys with this statesmanship and with JFK is the boomers. Like, it just isn't that anymore.

[Julia Claire]

John Jr. Was going to be the last great hope, I think, and maybe would have been that person for Gen X had he not breached his untimely end. And it seems like Jack is trying to kind of emulate that, too. He wants to be connected to that legacy. On his campaign website, there's a picture of him on a bicycle that is almost an exact recreation of a paparazzi shot of JFK Jr. So I think what I keep coming back to over and over Again, is that this is someone who kind of has a little bit of an identity crime crisis.

[Kara Vogt]

Yeah. I mean, I think that this is probably not unique to a Kennedy, but if you're going to pursue the family business with a name like that, it is impossible to figure out who you are without that history weighing on you. And it'd be one thing if a member of the Bush family went and opened a pizza shop. No one in the Bush family, as far as I know, has a pizza shop. And you don't have to think too hard about how Prescott Bush made Pizza or George H.W. or George W. Because who the F knows? But if you're going into politics, there is a thought and expectation about who you are and what you represent. I don't know what ended up happening. One of the Bush grandchildren was thinking about running for, was it governor or Senate in Maine? I don't know if he actually launched his campaign. But you know, what is a bush in 2025 in the midst of MAGA, you know, there is constantly both liberal nostalgia for the Bushes, but also MAGA hatred for them. When Dick Cheney died, I follow a lot of the right online because of my job. And there was a real good riddance that to me being 36 years, gosh, it was the most firebrand liberals growing up who were like, I wish death upon Dick Cheney. So to see the MAGA people, like, spitting on his grave, I was like, wow, we've really come far. So that is all to say that I can only imagine how hard it is to figure out how to be a person in general when you have a legacy behind you, a high profile one, and you're trying to be yourself against that backdrop. I don't know if it's a possible thing to pull off.

[Julia Claire]

And I think to your point, what is a Bush right now and what is the role of a Kennedy? I actually think that the person who has gotten it exactly right is Jenna Bush.

[Kara Vogt]

That's right.

[Julia Claire]

And that is the kind of. And honestly, I could see someone like Jack being equally as successful in a similar role in a non political, but still entertainment, still a very visible legacy of this family.

[Kara Vogt]

Well, he wanted to be an actor. I mean, look at Patrick Schwarzenegger. And I know that he comes by that for various ways, but Maria Shriver was a journalist. John Jr. Was a journalist. There is a way of being able to translate the life experience and the people, you know, for the rest of us. That I think is one of the most compelling ways to be a Kennedy right now.

[George Taveras]

Yeah. And when Jack was a kooky social media influencer and Vogue columnist. There was something sort of perfect about that. It was like, all right, that's exactly what we can do with you. And you can sort of serve that function.

[Julia Claire]

So you note in your profile, or what was supposed to be a profile last year, that it did end up falling apart, because as you said, the can kept getting kicked down the road. And one of the passages that I thought was really interesting that you ended on was. And now here I was, was just another journalist who tried to scale the walls of Camelot only to belly flop into the moat. What is it about the Kennedys that makes them court media attention and then simultaneously spurn it?

[Kara Vogt]

The best example that comes to mind for me is the royal family in England, that their power is only really derived from public attention. And yet to lend oneself publicly in the way that the royal family does is also to lose the really humanity of being a private citizen, of having things you do that are not publicly available for consumption. But the Kennedys are kind of the same. And this has been a repeating theme throughout the generations of knowing that having an audience and keeping America enmeshed in the myth and the legacy is like, there's only power as long as that's still true. Right? If every Kennedy decided today to go be a private citizen, this generation would have some questions and be like, huh, what's up with them? But probably by the time the next couple generations came through, we wouldn't think about it. Be like, oh, yeah, there used to be Kennedy. The same way that, like, there used to be, you know, other very famous families, Astors. I don't know if Astors are still around. That's probably not a good example. But this is all to say that it feels to me, it's a two way street, that there are at least some members of the family who aren't ready to give up on being this important family for America. I don't think every member of the family feels this way. And I think that great New York magazine piece the Kennedys got at this is like, how much mileage does the Avery family member want from being a Kennedy? But I think that they let us get close and push us away because they understand the public and their love of them sustains the family name.

[George Taveras]

Wow, that is a perfect place to end. It could be the final sentence of every. Of every episode of United States of Kennedy. Thank you so much, Kara. This was really great. And our best wishes to Jack. Sadly, Julia and I are not in his district, so we can't vote for him.

[Julia Claire]

But, Jack, you always have an invitation.

[George Taveras]

To come on the show, and maybe if you do, we will move to the Upper west side. I hear it's really affordable.

[Julia Claire]

Really, really nice.

[George Taveras]

Yeah.

[Kara Vogt]

And I would also say that no matter what you think about him and what he's up to, he's definitely going through a lot with Tatiana's promise.

[George Taveras]

Yes.

[Kara Vogt]

Nothing but good thoughts for her and her family as they're. As they're making their way through it. Yeah.

[George Taveras]

And from us as well. Thank you so much, Kara.

[Kara Vogt]

Thanks, guys.

[Julia Claire]

Thank you, Kara.

[George Taveras]

So that's it for this week's episode.

[Julia Claire]

Next week, we're talking about the history of Kennedy fashion. So subscribe and follow United States of Kennedy for all things Kennedy each week. United States of Kennedy is hosted by me, Julia, Claire and George Taveras.

[George Taveras]

Original music by Joshua Topolsky.

[Julia Claire]

Editing by Graham Gibson.

[George Taveras]

Mixing and mastering by Doug Boehm.

[Julia Claire]

Research by Dave Roos and Austin Thompson.

[George Taveras]

Our producer is Carmen.

[Julia Claire]

Our executive producer is Jenna Cagle.

[George Taveras]

Created by Lyra Smith.

[Julia Claire]

United States of Kennedy is a production of I Heart Podcasts.

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[George Taveras]

Janice Torres here, and I'm Austin Hankwitz. We host the podcast Mind the Small Business Success Stories produced by Ruby Studio in partnership with Intuit QuickBooks.

[Kara Vogt]

We're back for season four to talk to some incredible small business owners.

[George Taveras]

The big thing about working at tech is that it's ever evolving, ever changing everyone. That's how fast the industry is changing. So what I'm really excited about is to be part of that change. So listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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