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Jack Schlossberg

Episode Transcript

Speaker 1

What do you think about Jack Schlasberg.

Speaker 2

Well, I don't know a ton about him.

Speaker 3

I think he's hot and that's my main interest.

But I thought he was a little bit more contained than what I just observed on Twitter.

The first tweet that sucks.

Speaker 2

Me in this isn't all caps Happy birthday to Dax Shepherd's wife.

And then two spaces down Kristen, two spaces down Bell, two spaces down, all.

Speaker 3

Caps again Dax Shepherd, and then we go into normal text.

Speaker 4

Wonder if he'd ever have me on his podcast Space question Mark after he made racist comments about me space exclamation point, two spaces.

Speaker 2

Down, dackx all caps, did you get face filler?

Speaker 4

Space question where?

Speaker 5

And then I just started scrolling his.

Speaker 4

Page and I'm like, this man is insane.

Speaker 2

I don't know if he's just being an edge lord with this one, but this is another tweet we deserve to know if Megan Kelly was born with.

Speaker 4

Male or female genitalia four exclamation points.

Speaker 3

Justice will prevail.

Speaker 4

Wait, I have to find my other favorite one.

His tweets are.

Speaker 6

Just so off the wall.

Speaker 5

Where is that incredible to me?

Speaker 7

Oh?

Speaker 4

Yeah?

Speaker 6

He called gif me a bitch, which I just thought was funny.

Speaker 4

I mean RFK RFK Junior says no vaccines.

Speaker 2

But wants everyone to wear wearable My first Amendment right not to have an or ring.

Speaker 5

Corporate bitch that he talked kid's menu is DEI.

Speaker 2

I just don't even know what he's fucking talking about.

Speaker 5

I'm George Severes, I'm Lyra Smith, and this is United.

Speaker 6

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 talking about JFK's grandson and social media Jester Jack Schlossberg.

Speaker 1

You may have seen his speech at the twenty twenty four DNC or you may have seen him dancing shirtless on Instagram.

Either way, he's been getting people talking.

So where did he come from?

Speaker 6

So, like we said, he is jfka's grandson for most of his life he's currently thirty two.

I believe for most of his life did everything you would expect a young handsome Kennedy, especially one who is the literal grandson of JFK to do.

He was sort of tangentially involved in politics and the way you would expect.

He had a position at the JFK Presidential Library, where he was involved in selecting the recipients of various citizenship awards.

He spoke at the twenty twenty DNC in favor of Joe Biden.

He attended the Met Gala with his mom, Caroline Kennedy.

He went to law school.

He went to Harvard.

You know again, anything you might.

Speaker 1

Expect, Harvard and Yale got them, both, Harvard and Yale.

Speaker 5

I'm sorry, that's right.

I gotta catch them all.

Speaker 6

But then there was this sort of change that happened around early twenty twenty four when he became a very frequent poster on social media, and he is big on Twitter, he was big on Instagram.

Speaker 5

He has tiktoks.

Speaker 6

He now, you know, a year and a half later, has launched his own YouTube talk show, and he became sort of this weird anomaly where he combined the glamour of being a Kennedy with the sort of humor of being like a shit poster for lack of a better worse, and his content is very kind of unpredictable.

So his tweets and tiktoks range from traditional jokes that like a comedy front facing camera media might make to different characters and doing accents to literally pranks, like he lied about being Justin Baldoni's lawyer just to mess with people, and then the media covered it and then people had to like fact check it and uncover that it was false.

He sometimes will make fun of his own family, both his own immediate family and also the Kennedy name more broadly, and then sometimes he's more earnest, like he endorsed Zora Lundani for mayor of New York and posted a video while going to vote for him.

He's expressed his support for more progressive democratic politicians like Pritzker, and so you never know whether he is serious or whether he's not.

He's obviously, you know, very pot so people like watching videos of him, and he plays into that too.

He'll post videos of him shirtless or of him, you know, smugging at the camera, and it has led to some stuff.

I mean, he was hired as a Vogue political correspondent at some point and produced I don't know, somewhere around four articles total.

He has been on talk shows, he's been interviewed a couple of times, but he's sort of still kind of a.

Speaker 1

Mission ouside a cameo on Blue Bloods.

Speaker 5

I did not know that he had a cameo on Blue Bloods.

Speaker 6

There you go, so LRA, is he someone who is on your feed a lot?

Speaker 5

Do you get served as contact?

Speaker 1

Yes?

Speaker 5

And I got it before I knew who he was.

Speaker 1

Him singing ticket to Ride I think was the first video I saw of him, and I liked it.

Speaker 8

She's got a ticket to ride, She's got a ticket to rah h.

She's got a ticket to ride, but she don't care.

Speaker 6

I think I first saw him on Twitter, and he has there's this way of tweeting, both grammatically and syntactically, and also in his use of capitalization stuff that's almost and I mean this only inform and not in content.

It's almost Trumpian like.

He's almost making fun of Trump's style of tweeting.

So, for example, his pinned tweet right now you know as of July twenty twenty five, so apologetist.

This has changed his pin tweet is Jesus Christ's body type.

My thoughts colin Jesus was thin most popular guy of all time, not jacked toned, but not big.

So my question is did Jesus want to put on muscle but couldn't or was he lean on purpose talk soon Jack.

I mean, if you have been on Twitter sort of like throughout the twenty tens, you recognize this as kind of a classic shit post.

There are so many guys and you know, and women and people's fall genders who sort of tweet in this like half joking way, and the humor just sort of comes from the absurdity.

So I just thought he was kind of like a slightly self aware slash occasionally annoying hot millennial guys.

Speaker 1

But the thing about his tweets is that they're not drill like you know, this is a Kennedy and he's often talking about politicians, correspondents, serious news like people in the news.

But he continues to like ship post in the same style kind of no matter what he's talking about, unless he gets really sincere, which happens.

But the thing about that is that to me, it seems like he takes risks in that you don't know who's reading it and what they're going to understand as a joke or not, and it doesn't seem like he really cares if you get the joke or not, which is it's risky because you could offend people very easily if you were just simply putting things out there and saying, I don't care if you get it.

Speaker 6

In his relationship to humor and satire is I would say, generously inconsistent.

Like some of his his jokes are just very funny, and then other times it's completely out of nowhere.

I mean, a recent twek that I saw was which member of Trump's cabinet has had the most homosexual experiences and then he lists a variety of options.

Another one recently was Kid's menu is dei.

So of course the joke there is that the Kids' menu, because it appeals to children rather than adults, is a form of DEI.

Speaker 5

So you know, you sort of.

Speaker 6

See what he's going for there, And I want to get to the larger project, if there is any in his larger relationship to comedy, But I first want to go through some of our favorite recent posts of his, just so if anyone, you know, if anyone here is wisely not on TikTok or on X, they can kind of understand what we're talking about.

So, Lyra, do you have any that you made notice I do.

Speaker 1

Let me preface this by saying, many of the people whose opinion I greatly respect, really don't like him, but I do like him, and I can't hide it, and I can't fight.

I've been watching hours upon hours at this point now in preparation for this, but also months ago, and I think I absolutely tilt into the favorable group.

And one of the videos, or like the video that I think was like the turning point for me where there was no going back, is his video complaining or criticizing when people say, hey, man, have a safe flight.

Speaker 7

Have a safe flight, safe trip, have a safe flight, get there safe, be safe, have a safe flight, have.

Speaker 9

A safe flight.

How what do you want me to do?

Huh?

Speaker 5

What are you doing?

Speaker 1

It's like, on the one hand, he's saying that in general you're a passenger, you're not in control of the plane.

But also as a Kennedy people saying to him a man, have a safe flight, it has a different meaning.

Speaker 5

Yeah, it's funny.

Speaker 6

I would say that is a perfect example of like his content at its best.

I mean, first all, the premise is a classic stand up comedy premise.

Speaker 1

Well, it's Seinfeld complaining about the pilot, telling them like what altitude we're gonna be flying at?

Speaker 5

It's classic Seinfeld humor.

Speaker 6

It is genuinely a funny premis like, of course, to tell someone have a safe flight is a ridiculous thing.

They do not have any control over the flight they're going to have.

And as you're saying, he's using his identity as a Kennedy to humorous ends without I mean, yes, it's sort of gallows humor.

But he's not offending anyone, you know, he's not making some grand statement about the Democratic Party.

Speaker 5

He's not endorsing a candidate.

Speaker 1

Yeah, And I think that another one for me was his Valentine Stay video where he's just announcing that he needs a Valentine.

And I think that one I really liked because it's like the most self aware I've seen of him.

He's like comment subscribe at the end, like it's an obvious joke.

Speaker 6

Yeah, he likes playing with I would say even his identity as sort of a you know, internet crush.

He will often joke about.

One time he joked about going through a breakup and he was like, my heart is breaking.

And then I saw an interview with him where he said that people actually in his life texted him to say, oh my god, I'm so sorry.

Speaker 5

Heartbreak is so hard.

Speaker 6

And then he was like, oh no, I was completely kidding.

So he both exudes this kind of like single guy energy, but then he also has this distance with his audience, like he's not actually, you know, being horny.

Speaker 1

Yeah, there's really not a lot of dirt out there.

He's not stirring gossip about like his romantic life or his sex life at all.

Yeah.

Speaker 6

We talk about this later in the episode, but he does that classic Kennedy thing of being both overexposed and a complete mystery.

Like I see his content all the time, I would recognize him if I saw him.

I have now heard his opinions on a variety of issues.

But if you were to tell me at this point in time, where does he live, what is his day to day job, what is his plan?

Is he involved in politics?

I honestly would not really know.

Some of my favorites in terms of videos are he does this series with his dad where he just asks his dad questions and it's sort of charming because his dad is like pretending he doesn't want to be on camera, but then obviously is playing along.

There was this great video that is almost like hearkens back to a simpler time.

That's just him doing an Australian accent, and I'm pretty sure his mom is off camera and is just like laughing at him doing an Australian accent, which, you know, no matter what you think about Kennedy's, it is just charming to see a mother and an adult son, yeah, joking around.

Speaker 1

Early earliest ones.

And this is like pre even him being like all over TikTok.

Was him sitting And I also believe it's his mother sitting next to him laughing or or I think she's filming it.

And he's saying how much he hates eating in a restaurant in the middle of the day and.

Speaker 7

We have to say, wait there to eat something that we don't get to choose really what it is.

We only have a couple of choices, and you don't know what any of them are gonna taste like or what's good.

And we'll go eat there and it'll be covered in sugar, and then we're gonna sit there for most of the time and wait for some guy to come up and ask us some question.

Then we're gonna have to fucking talk to some guy about what we want to eat.

Speaker 6

Yes, Actually, restaurants are a favorite topic of his.

He has another one where he's like making fun of someone ordering at a restaurant and he's being like, we'll do the chicken, We'll do the salmon again.

It's like a classic stand up bit where he's like imitating someone ordering up at a restaurant.

Speaker 5

It's very like eighties.

Speaker 1

If you had the magic ability to delete or unsee anything that does really fit your personal desire expectation for this person and just be like delightedly surprised that he's really funny.

But there's no you know, filter like that.

Speaker 6

Yeah, So just to give people an idea of some of the things that he's done that have pissed people off that are not as charming as the ones we're talking about.

My example earlier, where he's speculating about which of Trump's cabinet members have had the most homosexual experiences.

That is, you could argue that's offensive to both the people he's accusing and you know, to gay people in general.

If he's using that as sort of like an accusation that it's something negative, obviously, you know, you could also argue that accusing people that espouse homophobic views of being gay is a way to kind of take them down a peg.

And accuse them of the one thing that they fear.

I'm sort of two minds about it.

I'm not gonna, you know, go out and protest because he is speculating that JD.

Vans is gay.

I could absolutely see the argument for why that is offensive.

I could see the argument for why that is stirring the pot in a way that is unproductive.

Who's to say, then there's more funny stuff that is so out of character.

Speaker 9

Like.

Speaker 6

Part of his job is presenting the Profiles and Courage Award to politicians and citizens that have shown courage, and one of the twenty twenty five recipients was Mike Pence.

So in the midst of all of this crazy should posting, he has a serious interview with Mike Pence about the courage he showed after January.

Speaker 1

Sixth, and it's you know, it's a pretty softball interview.

Speaker 7

What role should faith play in politics?

I know that your faith may have guided you in January sixth into or in many other decisions.

How has your faith played a role and how should faith play a role in our politics?

Speaker 6

Well, faith has ever played a role since the founding of this nation.

It's a topful interview because by definition he is quite literally giving him an award.

Speaker 5

He's not a journalistic.

Speaker 1

It doesn't seem like the same person, yes.

Speaker 6

Which is actually something I've noticed a lot.

Is he as almost these two personalities.

One is like millennial on funte, like he's a social media jester, and then the other one is like serious Kennedy.

His hair is perfect, he's wearing a suit, and he's like being interviewed.

Speaker 5

Along with his mom about the future of the Democratic Party.

Speaker 1

Yeah, I mean the offending tweet that pops to my mind first is the one where he said that Oosha Vance is hotter than Jackie oh.

Speaker 6

Right, which brings us to the question of why does he post.

I mean, obviously some of it is and he said this himself.

Some of this is just him entertaining himself and entertaining others and being funny.

But he does love to talk about how it's all for some greater purpose.

So we both have found interviews he's done where he talks about like his reasoning behind why he does all this.

Speaker 5

So in the simple as possible terms.

Speaker 6

When he was on Jimmy Kimmel, he was talking about how his goal is to get young people to vote basically, you know, using his platform as a young Kennedy to get young people.

Speaker 5

You have a big following on TikTok.

Speaker 6

How would you describe the videos you make for people like me who will not put TikTok on our phones.

Speaker 7

Well, I think what I'm trying to do with my videos is to bring some levity and some humor to serious political issues, something that you know so much about and do such a great job with on this show.

My videos maybe they're a little crazy, but maybe they're just crazy enough to work well.

Speaker 10

They have to be entertaining to get people interested in Your goal is to get people to vote.

Speaker 9

To absolutely get out and vote.

Speaker 7

My goal for being here tonight and my goal for the next few weeks is to get young people excited to vote, to vote for Kamala Harris, like I'm going to.

I was just in.

Speaker 6

And then when he was on Jen Saki's podcast, he talked a little more in depth about a strategy, and he was sort of saying that he felt Republicans are better at the social media game, especially post Trump, and are just better recording attention.

They're better according controversy, and so the reason he is posting in such a crazy and controversial way is because he thinks the Democrats can sort of like learn from their playbook.

Speaker 7

I think that the Internet is a place where it's difficult to break through, and it's difficult to break through, especially if you're not saying something that's controversial or at least somehow unexpected.

And I think that I see that Democrats play that game not as well as we could.

And I think that I use my judgment to make posts that I think are funny or silly but have a purpose either to make you think this guy's crazy, why is he talking about his own family that way?

But to be honest.

Speaker 9

Then you get all these retweets quotes.

Speaker 7

And everybody flips out about it, and I think that that's kind of the game that the other side has been playing really well, which is flipping people out and getting a reaction is almost half the battle.

And not every post is going to be hilarious or risky in some way.

Some of them have to be serious and boring, but they can't all be serious and boring, and so I think that it's very important to switch it up and to take risks, because I think that's not only entertaining for me myself as I laugh and post it on my phone.

But also a good way to signal to people that you're willing to either fight for them or speak your own mind, if you're willing to say something that's other people might not get or you know, might engender a reaction that some people don't like.

Speaker 6

And so that video is him answering a question about the tweet you were just talking about, Lyra, which is that he tweeted asking his readers whether they thought Oosha Van's was hotter than Jackie Oh, who is again his grandmother.

Speaker 1

This week, he released his new show on YouTube.

He released two episodes two days in a row, and within one of those episodes, he reads a news story response to the camera and then you watch live as he drafts and then posts a tweet about the news story.

And it is like really a window into what his processes with these tweets, and what is his process is just dumping out jokes and thoughts and not caring for a second it seems, you know, like how it's going.

Speaker 5

To be received.

Speaker 6

Yeah, he has this way of thinking where he sort of believes anything is fair game.

He's like, if I post something that is a lie, that is actually a commentary on misinformation, and I'm like making fun of the media ecosystem because they're going to pick it up and it's going to be on page six, and I'm actually doing social commentary.

If I post something that is offensive, that is because we need to take a page out of the Republican playbook and court controversy because it'll get people paying attention, and we need to appeal to young people that have a sense of humor.

If I post something that is earnest, it is because I care deeply about my family's legacy and my grandfather's legacy, and I really want to be a statesman like the other men and women in my family.

If I post something that is just a complete silly joke, it's because I think people should laugh, and I'm just entertaining myself and entertaining everyone else.

And it's actually not all that serious, and nothing is really serious.

So he there really is no gotcha question you can ask him.

And it's funny because I understand the perspective that his behavior is reckless, but I also tend to, you know, fifty percent of the time at least agree with him that there should be a little more like what's the word, sort of just like Jouis de vill to day to day political commentary, like it is engaging ultimately to watch this stuff.

Speaker 2

Yeah.

Speaker 1

The other thing that is interesting to note when he's like having these public takes on the current election in New York is that Andrew Cuomo was married to his aunt for fifteen years, and I just think that, oh yeah, I.

Speaker 6

Mean, once you start looking at the personal connections, he does not care about the fact that some of the people that he is dragging are you know, his own cousins and like people that were married to other family members, people that have Kennedy relationships.

I mean, he posted recently, I have never met Cheryl Hines, but if I did, I'd tell her she looks super dehydrated.

I mean, so he's pretty much saying that his cousin's wife is ugly.

And actually, I think one of the things that first started getting him attention in the political press was his open disdain for RFK Junior Because, as we've talked about before, it took a while for the rest of the Kennedys to sort of like condemn RFK Junior in an organized way, and from the beginning, he was just like my cousin sucks.

Speaker 1

Yeah, just saying flat out he's a bad person that you cannot trust and very much not the Kennedy way.

The Kennedy way is like you keep your mouth shut about the faults of your relatives.

Speaker 5

It's funny, like.

Speaker 6

The question of whether or not Jack's social media presence serves one big purpose is like designed to make you feel crazy, because, as you said, his process is just like firing off his thoughts at any given time, and he is just sort of vibes based.

Speaker 1

I do want to say I watched both episodes of Getting the Van, his new YouTube show, and I am saying this as a producer.

It's a phenomenally produced show.

The setup is perfect for him and he gets to be free do his thing.

It doesn't always work, sometimes it does.

Is there a sort of central gimmick to it?

Okay, there's a very shaky explanation of why he's in a van at one point where he says that he's going to drive across the country in the van and talk to everyone, and then he compares his van to the vans that they are using to grab people off the street and deport them, and he says he wants to do the opposite.

Speaker 6

With his I mean, again, this is classic Jack Schlosberg Gallows humor.

Speaker 5

It's like, if you squint, it makes sense.

Speaker 6

If you squint and you maybe have like a couple of Martini's, you're like, wow, he's kind of a comedic genius.

But if you take it literally, it really is a bit first draft.

You know, it's I gotta say, it's really giving freshman at the Harvard lampoon, pitching ideas for the big issue.

Speaker 1

For sure, but then with such confidence in charisma, well in the delivery the Kennedy.

Speaker 5

Chart, I mean, that's the confidence of charisma.

Speaker 6

Are in his DNA.

There's really nothing he can do.

There's no surgery he can get that can remove them.

So obviously we are a little more charmed by him than we would have maybe admitted.

Speaker 5

A couple of weeks ago.

But we also do recognize that he has flaws, so don't write in.

Speaker 6

But we wanted to talk to someone that has actually had a personal relationship with him and that has had a conversation with him.

So joining us today to investigate is William Cohen.

He's a business journalist and the co founder of the media company Puck and he was actually high school friends with jfk Junior, so he goes way back with the Kennedy family.

But for our purposes, he wrote a profile of Jack Schlasberg last year for Town and Country titled you don't know Jack, Bill, Thanks for chatting with us.

Speaker 9

Nice to see you both.

Speaker 6

So when we were looking up who to talk to about the topic of Jack Schlosberg and Jack Schlosberg's social media presence and his present and future as a sort of Democratic Party influencer, millennial influencer, we were kind of surprised to find this article you wrote for Town and Country almost exactly a year ago.

Obviously, you are a very accomplished business reporter or co founder of Puck.

This is not your normal beat, I guess.

So we were wondering, like, how did that come about?

Speaker 10

You'd be surprised when my normal beats consist of one of the books that I wrote, probably five or six years ago now, was a book called Four Friends, about four of my friends from high school, one of whom was Jfkate.

Speaker 9

Junior, John F.

Kennedy Junior.

Speaker 10

It was a profile of him, how he lived and how he died.

The story of the book was that I had four of these friends from high school, all who died young and tragically, and so it was a way to explore the meaning of life as well as how these guys lived.

I know, only knew them for three or four years, and obviously they had lives of thirty or forty years, So what was the rest of their lives like so, and how did they get there in the first place, all that kind of thing.

So I became one of those people pe Bull who had written about the Kennedys.

And so once you become one of those people who's written about the Kennedys, then sometimes you get asked to continue.

Speaker 9

To write about them.

Speaker 10

And I'm from Massachusetts, Central Massachusetts.

Kennedy's were always a central theme in my growing up and always been a big fan of them.

They obviously made mistakes and didn't live flawless lives, to put it mildly, but always were fascinating and inspiring.

And John was a friend of mine, and what happened to him was terrible.

I think his upside was huge, and so you know, naturally I've been interested in Jack Schlattsburgh and his sisters, his parents, given how much Jack resembles my friend John, you know, with a twist of his fond which makes a little more complex physical specimen than John Junior was, of course, you know, the ultimate male figure.

So anyway, I was, of course always impressed with Jack's academic accomplishments Yale, Harvard Business School, Harvard Law School, the Profiles and Courage Award every year, standing next to his mother talking about, you know, why they had chosen who they had chosen.

And then he seemed to develop this very unique social media presence which was sort of out of character for Kennedy's generally, and really kind of out there generally for people of his cohorts.

So just became really kind of interesting, What's Jack up to?

What's this all about?

Talked to Town and Country about that.

We agreed it would be an interesting peace and eventually, of course I tracked him down, found him living outside of New Orleans, believe it or not, and had a nice conversation with him.

I think this guy has a tremendous upside right up there with his uncle.

I know, people think he's engaging in sort of like bizarre behavior online.

And I have kids who are his age, so my kids don't do that kind of stuff.

I'm not sure I can fully relate to it, but I feel like he's relating to his peers and his audience and making an impression.

And this is just sort of the way you make an impression these days, are one of the ways.

And I think he's creative and smart and interesting and funny and clever, and yeah, it's not typical by any means, especially for somebody with his pedigree and his academic accomplishments.

I mean, why isn't he working in an investment bank or why isn't he working at Cravath.

I don't know, but he's doing this, and he's doing his thing, and certainly wouldn't be surprised to see him emerge in a political fashion at some point.

Speaker 1

Do you think that that's what his aspirations are?

Do you have any thoughts on what you think he's working towards based on the way that he's very he has kind of two sides.

He has the very polished public speaking side, and then he has the just full blown content you would make like if you were not a famous, notable person, that is pretty.

Speaker 5

Silly a lot of times.

Speaker 10

Well, he certainly cleans up well, right, I mean, he looks great in the suit.

He's very articular when he's talking about the Profile and Courage awards are at the convention.

He can definitely turn it on and he knows how to do that, and he can be silly and irreverent too.

Frankly, it is very charming and compelling and magnetic and captivating.

So what thirty two now or something.

I could certainly run for political office, not quite for president yet, but I wouldn't be surprised to see him do that.

I know he told me he was doing some acting gigs down in Louisiana.

He was probably working on a memoir.

I don't know where that stands now.

I didn't think that he had quite enough yet to write a memoir, you know, not going the traditional route, just like his uncle didn't go the traditional rutie who you know, he started George, and he definitely was thinking about running for political office at the time of his death.

Speaker 9

And I probably would have won.

Speaker 10

And you know, I've speculated that the two twenty sixteen presidential election could have been JFK.

Junior versus Donald Trump, with JFK.

Junior easily winning, but obviously that was not to be.

So, you know, I think Jack chooses this route.

I don't really see what the negatives are for him succeeding.

Speaker 6

He's sort of I think, despite the fact that he has this incredibly consistent output and that there is just so much footage of him online, he still remains sort of a mystery at his core.

I think part of it is because he's sometimes joking, sometimes being serious.

He sort of changes his vibe based on what's.

Speaker 5

In the news.

Speaker 6

There are certain things he reacts really strongly to, an other things that he ignores.

He has a sort of interesting relationship with the media, and that he's both suspicious of the media but also really just like his uncle, Yes, exactly eggs media narratives on.

So I'm wondering, you know, you spend time both with him but also just like looking at all his do you have a concept of like what his core beliefs are, what his political views are.

You know, if we're talking about a potential future in which he goes into politics, what would his public beliefs look like?

Speaker 10

Well, and I'd also just throw in that, you know, there was a period of time after he went a little bit wacky where he said I'm stepping off social media for a little while, see you later, guys, and then I don't know how much longer it was a month or six weeks he was back.

Speaker 6

I mean, well, of course, a huge part of being a social media influencer is constantly announcing or taking time off.

Speaker 10

Okay, well, you guys might know that better than I do.

There's no question what his political views are.

And he's very much progressive and the non Bobby Kennedy junior mold or the old Bobby Kennedy junior mold back when he was doing Riverkeeper and being an environmentalist.

No, he's very much in the family mold, you know, very I've spoken very anti Trump, anti isolationism, immigration, you know, all the things I think that make America great again, honestly, and not what the MAGA movement thinks makes America great again.

So I think he would have I mean, he'd be like a total breath of fresh air.

I think he'd have a lot of success politically if we can never make it through the period they we're in now, and he would ever decide to turn his attention to politics.

Speaker 1

I mean, the thing about the influencer side and the influencer role in general, is that target audience is split.

That's part of the fervor that people feel about influencers is that a lot of times half of them are following just to criticize or to take part in looking for faults and looking for things to make fun of them for complain about.

It just makes me wonder, what do you think that we expect or desire from a Kennedy today that's different than in the past, or is it the same.

Speaker 10

I wrote a piece a couple of months ago about the feud among the family against Bobby Junior.

But one family friend says something to me which really got me thinking, You know, to people in their twenties even know who Carolyn Kennedy is.

So Carolyn Kennedy does this video coming out against Bobby Junior.

As I mean, people at my age think, whoa Carolyn Kennedy, Ambassador to Australia, the Bassard in Japan.

She never talks to the press, She's always controlled, she never criticizes anyone in the family.

Then she makes this video that's against her own cousin and frightly so obviously, and we're all like jaws on the ground.

Did you see the video that Carolyn Kennedy just made and released and then somebody said, but yeah, but how many people twenties third even know who she is, let alone caere And I think there's an element of that.

So I think, like every generation, there's delusion and dissipation of the family fabulousness, and I think to some degree we're seeing that, although there's a lot of people in that generation who are the new generation, who are quite accomplished, and so I think because of the Kennedy name, a lot is still expected.

When somebody with that name and that pedigree shows themselves to be talented or differentiated or politically oriented, immediately a lot.

Speaker 9

Is expected of them.

Speaker 10

I mean, if Jack we're working at Goldman Sachs, I don't think a lot would be expected of him.

But when he's making political videos and being overtly political and raising the question of whether he's going to go into politics, then immediately a lot is expected of him.

I don't think much was expected a John Junior when he was in the DA's office, although he did a good job when he started George and ran George again.

I think he proved himself that that was a magazine ahead of its time, and he did a lot of very clever things, although managing the finances was not in his sweet spot.

But then again, when he started to think about turning to politics, whether to run against Hillary Clinton for senator from New York or governor against Pataki, I think people really started to get excited and thought wow.

When he appeared at the convention, that was just a really wow moment.

Speaker 9

Right.

Speaker 10

I think when Kennedy's start tilting towards politics, a lot is expected of them still, even if most people don't know who Carolyn Kennedy is anymore.

Speaker 6

Do you think the fact that RFK Junior is so off the deep end in terms of what is expected of a Kennedy means that, in a weird way, the window has opened for Jack to be a little more unhinged on social media.

And it actually is not that big of a deal because at least his politics are correct on line with the family.

Speaker 10

Yeah, I don't think people in this family are criticizing him for his you know, sometimes wacky videos.

I mean, the family is much more critical of RFK Junior obviously, because he seems to have like totally gone off the deep end, you know, the whole running for president and then dropping the campaign and then endorsing Trump and somehow getting in the cabinet and all these sort of wacky policies that he's espousing from a position of power is definitely not what is typical for this family.

The rift is not uniform and universal.

I think obviously his family, his children support him, most of them, while pretty much everyone else in the family is on the other side.

Speaker 6

Did you ever hear from Jack after your piece came out or have you been in touch with him at all over the last year?

Speaker 1

Oh?

Speaker 10

Actually, he did write me and said basically, he said he thought it was really fair and complimentary.

But I've tried reaching out to him since, you know, for the next article, and he didn't respond.

My thinking was that maybe other people wondered why he had spoken to me, and maybe that wasn't the smartest thing for him to do, although I don't know why not, but whatever, and so he wasn't He might have been so like, Okay, now I'm done engaging with the media again, or this guy in particular, I don't you know.

Speaker 9

Yeah, that's just sort of speculation on my part.

Speaker 1

Well, and you know, like very recently he's been so vocal against the Ryan Murphy Show.

Have you seen this.

Do you know what I'm talking about?

Ryan Harfy's doing a show about JFP Jr.

And Carolyn Bessaid, and Jack is frequently posting things and calling Ryan Murphy like a pervert ease.

Speaker 5

He said he looks like a thumb the other day.

Speaker 9

Okay, I've missed some of this.

Speaker 1

It's been going on, And what really are there expectations for how they're represented?

Speaker 10

Well, it was the culture massively public figures, right, So they're going to be represented in any number of ways, some of them flattering, some of them not.

For the article I did about the sort of internescing warfare related to Bobby Junior, I talked to Larry Lehmer, who wrote The Kennedy Women, and he was finishing up or his new book about Andy Warhol was coming out, but then he was going right back to writing a new book about Jack Kennedy.

The father found some stash of a secret stash of letters or something that he was so excited to go through and then write another book about this guy.

And now there's been this rash of books about Carolyn Bissett and Carolyn and John and now there's this series or whatever it's going to be about them.

So they're you know, massively public figures, have been you know, their whole lives.

I don't think there's anybody who can really still compare to them in terms of being sort of massively public figures.

Not the Bushes, not Obama, not Biden, not Trump.

I mean, you know, so you know, I think like that, you know, once people get done, you know, digesting and hopefully you know, getting beyond what Trump has been doing to us.

I don't think anybody's going to be writing books about Donald Trump fifty years from now because you know, the new letters emerge or or you know something about his exotic lifestyle or whatever it is.

You know, this is just not that interest in that.

I mean, this family was you know, glamorous, and you know, I mean, was there ever a more beautiful couple than John and Jackie?

I mean, I don't think.

Speaker 7

So.

Speaker 6

This is something we keep sort of writing into with people of all generations, and I think now with jack Schlassberg it is revived in some younger people.

It's just like this idea of the Kennedy effect, Like when you are in a room with them, or even when you watch them on television, there's just something about the charm and about the chrisma that works on you even if you don't want it to.

So you know, as someone who knew JFK Jr.

In person, someone who has met various members of the family, what is that like in person?

Speaker 10

Well, with JFK Jr.

It was unlike anything I've ever seen in my life.

And I've met Obama and was obviously quite impressed and taken with him.

But John Junior, I mean, it was he just warped the room, He warped the behavior of other people.

Speaker 9

He was.

Speaker 10

I mean, he was just the brightest, shining celebrity in any room.

Speaker 9

And I mean just like it was.

Speaker 10

A buzz went through the audience as soon as he walked into a room.

Was there, Oh my god, these JFK.

Junior's here.

But you know, obviously, you know I was friendly with him, and we transcended all of that, of course, But you know, I would just stand back and watch it on many occasions and just sort of be in awe of it.

Speaker 5

Specific instances or moments come to mind.

Speaker 10

Oh, I mean, certainly there due I mean I remember once I think I told this story in the book, but I was working at are at Rockefeller Center, and I lived on the Upper West Side, and so would walk home on a nice night from Rockefeller Center to my apartment on Riverside Drive.

And I was walking up Broadway and got to Columbus Circle to what used to be the old Paramount building, which had a movie theater in the basement.

Now it's some sort of Trump building.

It's where Jean George is right there at the Columbus Circle.

I was walking by and finding my own business, and John rode up on his bicycle and there was scaffolding around the building.

They were doing one of their numerous refurbishments of the building.

And he locked his bike to the scaffolding and said hello, and we started talking and reminiscing and catching up.

And the first thing I noticed it is fly was down, and I told him about that, and then.

Speaker 9

We're in time for like twenty minutes.

Speaker 10

Finally he says to me, well, you know, I really should go because.

Speaker 9

I'm facing on her name.

Speaker 10

Who is the actress who was in Splash, who's married now, Hannah Daryl Hannah Darryl.

Is you know, waiting for me inside to go to the movies?

Said John, Why in the world are you sitting here talking to me when Darryl is waiting for you down in the movie theater and you're twenty minutes late.

Now, you didn't need to spend time with me talking about nothing.

You know, Darryl is going to be pissed.

Well, that's just the way it was with John.

You know, he was very much like in the moment and very absent minded and lost his wallet, lost his bike, blah blah blah.

And yet but eventually he kind of you know, he definitely got it together.

I mean, to start and run and produce a magazine like George every month, I mean that requires a lot of skills organizational and leadership and editorial judgment, and he pulled it off.

Speaker 6

I Mean, you mentioned a lot of the similarities between JFK Junior and Jack in the piece, and obviously a lot of them have come up in this conversation.

There's a real parallel between George Magazine and Jack's Instagram, just in the sense that each of them is like the media form of its time.

It's like, of course, in the nineties, what you would want to do if you wanted to be a media figure is start a sexy political magazine that sort of like you know, Vanity fair esque and then, of course now the cool thing to do is to do vertical short form video.

A lot of the similarities are very self evident, but I'm wondering if there's anything else that you can talk about in terms of the parallels you see between Jack and his uncle.

Speaker 10

There's obviously a physical appearance, there's similarities.

I think Jack probably has more raw intelligence than John did.

Not to say that John wasn't smart, because he was, but he was lazy.

Speaker 9

He was intellectually lazy.

Speaker 10

I think Jack is obviously quite gifted intellectually.

Jack Schlasburg he had a much more normalized upbringing, except that he you know, he did spend time in Japan when his mother was ambassador of Japan, and in time in Australia when his mother was an ambassador to Australia.

But you know, you know, his father wasn't President of the United States, and you know, assassinated.

Speaker 6

Can I ask you one final question, do you have any sense of what Jack's social life and social circle are like?

I'm realizing, you know, we're talking a lot about JFK.

Junior and his various friendships and the people he surrounded himself with.

I mean, George Magazine was a very collaborative effort, and it just sort of occurred to me in this conversation.

You know, all of Jack's videos are just him or just him with a member of his family.

He's not like a he doesn't have sort of the socialite tendencies that some of the other members of his family have.

And I'm wondering what is his day to day like, not that you have answered that question, you.

Speaker 10

Know, well, I did ask him, you know, did he have a girlfriend, And you know, he didn't want to get into his personal life, which you know, I felt like I had to ask because everybody wanted to know, and I felt like I wasn't surprised that he didn't want to answer.

You know, I think there's a lot of speculation, but I think you know, when he's what thirty two now, right, I was married by that time.

I think people are curious what is so well, I think people are curious, like what he does.

I mean, he was, you know, covering the election for Vogue.

I mean, I don't know how many articles he produced there or how or why he got I mean, I guess I could figure out why he got that, but you know, I'm not sure how qualified he was for it, but again, he's pretty smart.

But you know, Okay, that's over.

I don't know what he's doing now.

I know he's moved back to New York.

Speaker 5

Yeah.

Speaker 6

It's another element of the mystery at the center of this personality is he's both complet overexposed and also completely mysterious.

Speaker 9

And I'm sure that is by design.

Speaker 6

And it's a very Kennedy thing to be both overexposed and unknowable.

Speaker 10

Right, And I think John Junior was plenty overexposed, but more knowable.

Yeah, I think he was less mysterious, at least to me.

I mean maybe it's because I knew him and friends with him, but yeah, you know, I think we knew who he was dating and you know what he was doing, right.

You know, when I got done with that article and after talking to him, people would ask me, and I would say, I think he's got a very steep trajectory.

I think he could do whatever he wants to do, sort of like John Junior at that age.

He can do whatever he wants to do, and I think people will embrace it and give him a chance.

Speaker 5

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

Speaker 6

Join us next week for the second Kennedy film of the month, We're talking with Hunter Harris all about Pablo Lorraine Jackie, the twenty sixteen films starring Natalie Portman as Jackie Kennedy in the aftermath of JFK's assassination.

Speaker 1

Right, go and rewatch it, or, in the case of almost everyone I tried to talk to you about it, watch it for the first time and listen next Monday.

So subscribe and follow United States of Kennedy for all things Kennedy every week.