Isaac Chotiner on Confrontation, Curiosity, and Being the 'Interview Assassin'

Summary

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On with Kara Swisher

Episode: Isaac Chotiner on Confrontation, Curiosity, and Being the 'Interview Assassin'

Date: January 5, 2026
Host: Kara Swisher
Guest: Isaac Chotiner (Staff Writer, The New Yorker)

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Episode Overview

This episode features a deep dive into the art and ethics of interviewing with Isaac Chotiner, notable for his incisive, often relentless Q&As in The New Yorker. Kara Swisher, herself a famed interrogator, probes Chotiner on his approach to confrontation, preparation, handling difficult guests, media criticism, journalistic partisanship, and what it means to hold power to account in 2026’s fractured media landscape. The conversation covers the reputations both have developed for being “tough,” how they think about getting real answers, and the growing challenges facing journalists with hesitant or hostile subjects.

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Key Discussion Points & Insights

1. Chotiner’s “Interview Assassin” Reputation and Style

• Swisher probes Chotiner’s tough interviewer image

  • “You have a reputation for getting powerful people to tie themselves into verbal and intellectual knots.” (03:27)
  • Chotiner downplays the ‘assassin’ label, noting, “I try not to do the majority of my interviews that type… it tends to be the ones that go viral.” (03:46)

• Interview Format: Phone vs. In-person

  • Chotiner values the phone for its emotional distance:
    • “It’s easier to have a confrontational interview [on the phone].” (04:28)

• Types of Interviews

  • Chotiner divides his work:
    • “There are kind of one of two categories. The first is you’re interested in the person… the second is you’re interested in their expertise.” (05:13)

2. Preparation and Process

• Selection and Planning
  • Chotiner collaborates with his editor and colleagues for interview targets:
    • “It’s some combination of what’s in the news, things that personally interest me, and things someone brings to my attention.” (06:29)
• Preparation Depth
  • Swisher and Chotiner both: meticulous research is essential—even when feigning naivete for the audience’s benefit.
    • “I would sort of play the role of… the person who didn’t know and was asking these experts questions, the way average people… were wondering what was going on.” (09:31)
  • Chotiner admits journalism carries a certain fraudulence:
    • “You sort of inherently come across as knowing more than you do… It’s all bullshit to some degree.” (10:53)

3. Objectivity, Opinion, and Fairness

• On Bringing Opinion
  • Chotiner: letting his own perspective in allows for richer questions without false neutrality.
    • “I can ask questions that make it clear what my point of view is and not feel like that’s violating the terms of the interview.” (12:10)
• Trust and Transparency
  • Swisher agrees: “Truthful, not neutral… I think you get more trust.” (13:39)

4. Landing and Conducting Tough Interviews

• Convincing Reluctant/Hostile Guests

  • Chotiner: “You can’t promise things that you can’t promise. You can’t say things are going to be off limits.” (15:15)
  • Both prefer to reach out to subjects directly for more genuine results: “I actually prefer text if possible.” (16:02)

• Balancing Preparedness and Flexibility

  • Chotiner doesn’t script everything, keeps things flexible, especially if the topic is more familiar.
    • “I have kind of notes in front of me… but I try and keep it flexible… feels stifling if I’m just reading questions.” (16:33)

• The Power of Listening

  • Chotiner finds even when paying attention, reviewing transcripts reveals missed nuances:
    • “I’m always surprised… that there are things that I missed or nuances I missed.” (18:09)

5. Written vs. Audio Interviews

• Chotiner prefers print
  • He appreciates the Q&A format’s ability to edit for precision but admits tone can be easily misread.
    • “Written words can be misleading… People can give responses that seem hostile when they’re not.” (19:30)

6. Handling Viral/Career-Defining Interviews

• High-Profile Catastrophes
  • Swisher asks about the “career-ending” Karine Jean-Pierre interview:
    • Chotiner: “My goal isn’t to make people look foolish… we all have contradictions and hypocrisies.” (24:18, 25:19)
  • On ‘gotcha’ questions:
    • “If people have some hypocrisies or contradictions, then they can say, ‘Yeah, I’m a hypocrite.’” (25:59)

7. Limits and Ethics

• Where Chotiner draws the line
  • He avoids questions about private consensual behavior or inviting petty professional criticism. (28:13)

8. Critiquing Other Journalists/Public Media Feuds

• Chotiner is unabashedly critical of bad journalism:
  • “There’s a lot of terrible journalism out there and seems worth paying attention to, pointing out. Making it better.” (40:54)

9. Access, Media Environment, and the Future

• Journalist Access Shrinking
  • “It’s gotten harder and harder to get Republicans to talk… I’ve stopped trying as much as I used to.” (15:05, 42:49)
  • Swisher: “They don’t need [the media] at all—it’s direct to customer, essentially.” (41:19)
• Power and Censorship
  • The duo discuss mounting pressures from ownership and government during regulatory/merger moments (CBS, Paramount, Warner Bros.).
    • Chotiner: “It’s really bleak and depressing times… the Trump White House has smartly understood that… regulatory approvals [can be] conditional on kissing the ring.” (45:22)

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Notable Quotes (with Timestamps)

• “You have a reputation for getting powerful people to tie themselves into verbal and intellectual knots.”
  — Kara Swisher (03:27)

• “It’s easier to have a confrontational interview [on the phone]… like the old joke about how it’s easier to break up with your spouse over the phone.”
  — Isaac Chotiner (04:28)

• “I can ask questions that make it clear what my point of view is and not feel like that’s violating the terms of the interview.”
  — Isaac Chotiner (12:10)

• “It’s all bullshit to some degree.”
  — Isaac Chotiner, on journalism’s ‘fraudulence’ (10:53)

• “I think hiding a point of view has always been a mistake… Truthful, not neutral.”
  — Kara Swisher (13:39)

• “If people have some hypocrisies or contradictions, then they can say, ‘Yeah, I’m a hypocrite,’ or they can explain it… highlighting those things is a really interesting way of looking at where people’s blind spots are…”
  — Isaac Chotiner (25:59)

• “The reason I want to talk to people is to find out if they’re dumb.”
  — Isaac Chotiner (52:14)

• “Once Trump is… no longer president, is the country going to revert to some sort of normalcy in whatever that meant pre-Trump?”
  — Isaac Chotiner (55:03)

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Timestamps for Key Segments

• [03:00] - Introduction to Chotiner and his interview approach
• [05:10] - Types of interview subjects and formats
• [09:31] - Preparation and knowledge (or lack of) as interviewing tactic
• [12:10] - Distinction between reporting and opinion; views on neutrality
• [15:15] - Strategies for convincing guests; limited promises
• [16:33] - Preparedness versus flexibility in the interview process
• [18:09] - Importance of listening and surprises in transcription
• [19:30] - Print Q&A vs. podcast/audio—challenges with tone and editing
• [23:38] - Discussing viral, controversial interviews and their afterlife
• [25:59] - 'Gotcha' questions and exposing contradictions
• [28:13] - Chotiner’s ethical boundaries
• [40:54] - Criticizing bad journalism and public media feuds
• [41:19] - Decline of access/interview opportunities for journalists
• [45:22] - Pressures from executives/politics on newsroom independence
• [51:49] - Interest in investigative reporting over “principals” interviews
• [55:03] - Big questions for 2026 and what comes after Trump
• [56:42] - How to (hypothetically) interview Trump as an exit interview

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Memorable Moments

• Chotiner compares interviewing to breaking up:
  “[It’s] easier to have a confrontational interview [over the phone]… like the old joke about breaking up with your spouse over the phone.” (04:28)

• Swisher and Chotiner both revel in heightening discomfort:
  Swisher: “I don’t mind them getting upset in front of me or being upset or being rude back at me.” (36:28)

• On trying to find out who’s actually ‘dumb’ among the powerful:
  “The reason I want to talk to people is to find out if they’re dumb.” (52:14)

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Outside Expert Segment

• Anna Sale (Death, Sex & Money) asks:

  • Do you aim to break through public figures’ self-presentation?
    • Chotiner: “Absolutely a goal is to try and get people who… haven’t said [something] a million times before.” (31:15)
  • Is it easier to be incisive with someone you aren’t personally aligned with?
    • Chotiner: “If you’re more aligned with someone… it’s definitely worth trying to remind yourself… you may not be paying as close attention as you should.” (32:18)

• Most intimidating interview?

  • “The most intimidated I ever was… was the novelist V.S. Naipaul at his house in London… He was quite bullying.” (33:02–33:41)

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Final Reflections & Closing

• Story selection/people Chotiner still wants to interview:

  • Narendra Modi would be his #1 get; regrets not landing Henry Kissinger. (43:52)

• Swisher’s hypothetical first question for Trump:

  • “Did your parents hug you enough?” (57:45)

• Chotiner reveals a personal tidbit:

  • “I’m a big Houston Rockets fan and very… anxious fan. Don’t handle my emotions well about it.” (58:04)

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Takeaway

This episode is a master class in the modern interview: equal parts confrontation and curiosity, method and instinct, vulnerability and persistence. Chotiner and Swisher dissect not only ‘how’ they do what they do—but why forthrightness, transparency of perspective, deep research, and a willingness to make subjects and audiences uncomfortable are critical to journalism that matters, especially in an age when power too often refuses scrutiny.

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Transcript

[Kara Swisher]

I'm more explicit than you are. I'm like, what you're doing here is this, and you look like an idiot. And I actually say you look like an idiot. And it tends to work, especially with men.

[Isaac Chotiner]

You can try it here if you want.

[Kara Swisher]

No, that's okay. You're not. I don't need to. I would if I had to.

[Isaac Chotiner]

It's on.

[Kara Swisher]

Hi, everyone from New York magazine and the Vox Media podcast network. This is on with Kara Swisher. And I'm Kara Swisher. My guest today is Isaac Chotner. He's a staff writer for the New Yorker and a principal contributor to the magazine's Q and A series. Chotner is famous for his intense and sometimes relentless ways of questioning his guests. Last year, he went viral for contentious conversations with former White House press secretary Karine Jean Pierre and legal scholar Cass Sunstein. Chotiner also isn't afraid to call out other journalists when he thinks their reporting lacks substance, something I completely endorse. I like what Isaac is doing, and one of the things I'm going to do this year is focus on people whose work I like. And of course, since we do interviews all year long, I want to talk to someone who I think is one of the better interviewers these days. In fact, one of the best. He's doing a lot of things that other people aren't, which is sort of celebrating his own idiosyncratic style and also really drilling down and getting real answers out of people. Something I try to do and not always successful at doing. And he often, often is. So let's get to my conversation with Isaac Jones. Our expert question comes from Anna Sale, host of the Slate podcast Death, Sex and Money, also an amazing interviewer. Don't go anywhere.

[Isaac Chotiner]

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[Kara Swisher]

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[Kara Swisher]

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[Isaac Chotiner]

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[Kara Swisher]

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[Isaac Chotiner]

Rage, babe, is kind of the currency or the power that's behind a lot of the content we might see this.

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[Isaac Chotiner]

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[Kara Swisher]

It is on. Isaac, thanks for coming on on.

[Isaac Chotiner]

Pleasure to be here.

[Kara Swisher]

So do you know why you're here?

[Isaac Chotiner]

No.

[Kara Swisher]

Because you're one of my favorite interviewers and I interview for a living and I've decided to please myself in 2026.

[Isaac Chotiner]

Well, it's very nice of you to say.

[Kara Swisher]

Yeah. So I want to talk a little bit about your craft and a bunch of things. And one of the things, I was at dinner last night with a lot of people and they are also fans of yours, but they don't know anything about you, like at all, which is really interesting. And of course I'm like a promiscuous blabber about myself and my family and everything. So I want to talk a little bit about that. But let's talk about the craft itself. You have a reputation for getting powerful people to tie themselves into verbal and intellectual knots. On the record, it's earned you a pretty intimidating nickname, the interview assassin. I don't know, are you amused by that characterization or does it miss something about your approach?

[Isaac Chotiner]

You know, it's fine. I guess I try not to do the majority of my interviews, that type of interview, which tends to kind of be the ones that go more viral on Twitter or whatever else. But, you know, it's. It's nice that people are reading and enjoying the work, I guess.

[Kara Swisher]

Do you think about it when you're doing it or do you feel like you have to live up to that or not at all?

[Isaac Chotiner]

No, no, not so much. I, you know, I guess maybe I kind of have an aggressive style in terms of asking questions, but I, it, you know, it's just sort of the way I do interviews, I guess. So I don't think about it consciously too much.

[Kara Swisher]

Do you think it's because most people do interviews not in that way or that are too soft? I think I think that's the case. But.

[Isaac Chotiner]

Well, you know, there's certainly a lot of interviews that are too soft, but I think that there are different ways of doing interviews that are hard hitting or whatever else. You know, I think one, one advantage that I have is that I get to do a lot of interviews over the phone. I do some in person and I do some with video over zoom, but a lot of them are phone interviews where I'm just talking to the person, I'm not seeing their face. And for me, that's much easier to do an interview that can be confrontational or, you know, there's like the old joke about how it's easier to, you know, break up with your spouse over the phone or whatever else. It's easier to. It's easier to have a confrontational interview. So I. I think for. For those types of interviews, I'm fortunate to be able to do them over the phone.

[Kara Swisher]

And what, do you pick that as a thing? Because most people don't do those anymore, right?

[Isaac Chotiner]

Yeah, no, I. I prefer them. I mean, you know, if it depends on what the interview you're doing. I tend to think of interviews as being kind of one of two categories. This is obviously very broad. The first is you're interested in the person you're talking to, and the second is you're interested in their expertise. And, you know, if. If a news event happens and I'm interviewing some. Someone about, you know, a coup in Turkey or something, usually the person I will interview, it's not that people are interested in what this historian of Turkey, what their personal life is like or what their office looks like. They're interested in the news they have to offer, the analysis they have to offer. And then there are interviews where you're talking to Jonathan Franzen or Zadie Smith or whoever else. And I think people then are more interested in kind of a little bit of scene, a little bit of, you know, what this person was like, where you met, so on and so forth. So I. I tend to think of the interviews in one two ways.

[Kara Swisher]

And do you choose who you interview, how much input and how does that happen? Talk a little bit of the process.

[Isaac Chotiner]

Yeah. You know, I talk to my editor, who's a wonderful editor named Micah at the New Yorker, and he and I talk about it. I get, you know, I get ideas from my boss, from other editors at the magazine, from colleagues. I'm always asking people, my friends, you know, who'd be an interesting person to talk to. What's the subject matter I should be looking into?

[Kara Swisher]

Yeah. Is it strikes your fancy because some of them are off the beaten track. Some of them are people that are in the news, essentially.

[Isaac Chotiner]

You know, it's some combination of what's in the news, things that personally interest me. I think if you read my interviews, you'd get some sense of subjects that I'm particularly interested in. And then, you know, just things that. That seem interesting to me that someone brings to my attention. And, you know, it's the way I get a lot of the stuff.

[Kara Swisher]

Let's talk a little bit about your influences in the genre. You've mentioned David Marchese. I like him very much in the New York Times. As someone whose work you like.

[Isaac Chotiner]

Yeah, very much.

[Kara Swisher]

I would say Tom Snyder. I know it sounds crazy from way back when. You don't know who that. Maybe you do, or maybe.

[Isaac Chotiner]

Of course, he was after Letterman. I used to watch his show all the time. Yeah.

[Kara Swisher]

Yeah. Back in the sort of the early days when I was a kid. I know it sounds crazy, but I always enjoyed Barbara Walters. There's all kinds of people like different things that they did that made me laugh. Obviously, Dick Cavett was a big influence on me because I'm old. Who do you look up to?

[Isaac Chotiner]

That's a really good question. You know, Tom Snyder's an interesting one. I hadn't thought about him, but he would have these absolutely fascinating interviews. One person who I think is actually an incredible interviewer, and I've. I've thought about trying to not mimic, because that's for obvious reasons, is Howard Stern, who has an ability to get things from his guests that I don't feel like. I totally understand how he does it. But I've thought that there's something. I think it's. It's something about the kind of vulnerability he shows, the self deprecation he shows. There are other aspects of Howard Stern which I'm less interested in mimicking, but. But there's something about how he talks to people of vulnerability that I think really lets people open up. And I think that, that, you know, I don't go into my personal life when I'm interviewing someone.

[Kara Swisher]

No, you don't.

[Isaac Chotiner]

Trying to show that vulnerability is, I.

[Kara Swisher]

Think, important, which is kind of impossible without being personal, right?

[Isaac Chotiner]

Yeah. I mean, you can be self deprecating. You can make a joke, which I think my theory about making jokes with people you're interviewing, you know, to start things off, is they either think it's funny, which is good, or they don't think it's funny, but therefore they kind of look at you with a certain amount of pity, which is also a source of vulnerability.

[Kara Swisher]

That's one of your tricks.

[Isaac Chotiner]

So, you know, I think there are ways to do it. So that would be another example.

[Kara Swisher]

And what is your trick there? Because that's a trick, right? I have a bunch of.

[Isaac Chotiner]

Is that a trick? Oh, I don't mean that. I'm like writing down jokes before an interview to come up with.

[Kara Swisher]

No, I'm saying is that something you think works for you or what works best for you?

[Isaac Chotiner]

I think trying to set a lightish tone to start off is. Is important. Yeah. It doesn't want to seem too severe at the beginning. Yeah.

[Kara Swisher]

So let's talk a little bit more about what makes a good interview and your style. We're going to talk about your reputation in a minute. But tell us more about process, because we have a process here. I have had one for a long time. It's changed over time and again. You don't do as many high profile figures as you said. They're more informational with an expert on the subject. What do you think makes an interview a success for you? And talk about beforehand, because I don't think people know. Everyone's always asking, do you prepare before? And I'm like, well, obviously we do. Like, what do you think? We just like, sit down and just start blabbing away. I mean, I guess they're used to cable news or something. I'm not sure why they think nobody prepares. But talk about your prep.

[Isaac Chotiner]

Well, I guess I should start by saying, you know, it's very different for a subject that you have some knowledge of or versus something that you're kind of coming into fresh because of the news. Right. And so, you know, some interviews take a lot longer than other interviews to prep. You know, during COVID I was doing a lot of interviews in the first year and I, I'm pretty, pretty stupid about medicine and science and all these things. And, you know, I thought that at least in that case, a lot of people were coming to this subject fresh and didn't know much about it. And so I would sort of play the role of smart person. No, no, no, not the smart person. The person who didn't know and, you know, didn't know what was going on and was asking these experts questions, you know, just the way average people, I'm being one of them, thought about, were wondering what was going on. And then there's subjects where you know more about. And so it's easier in most cases. But, you know, for me, I think part of what I try and do with these things is on subjects I'm interested in, be constantly reading and trying to find people who I think are saying interesting things about these subjects. And so then when I decide to do an interview about, you know, I have sort of a list of people or people in my in mind to turn to.

[Kara Swisher]

Do you feel vulnerable in those moments to admit you're not an expert? Is that because a lot of reporters try to come off as a lot smarter than they are? I've always noticed when in fact they aren't or I don't know is never used. And I do it a lot. I'm like, I don't know.

[Isaac Chotiner]

Yeah, I mean, I think one aspect of sort of whether you're a commentator or a writer is that Part of journalism is you sort of inherently come across as knowing more than you do. I remember I reviewed a book about the history of sugar. This was probably 15 or 20 years ago. And I remember my grandmother saying to me, like, I had no idea that you knew so much about the history of sugar. And I said, well, I don't. This is just what happens when you review a book and you can sound that way. It's all bullshit to some degree.

[Kara Swisher]

Right.

[Isaac Chotiner]

But no, I don't think. I think journalists should be upfront about things that they don't know. And I. That there's some things that I don't know that I would not want to do interviews about because I would just feel too deep in the weeds. I feel like I couldn't do it. And then I think in other areas, like I said kind of when Covid was starting, I think there's a way to try and use your lack of knowledge and say most people reading this don't have great knowledge of it. And I'm going to kind of use that to inform readers in some way.

[Kara Swisher]

You also have to, though, ask the smart can't be dumb. Right. You can't be someone who has no curiosity. It's a curious person.

[Isaac Chotiner]

Yes. Yes. That's a good distinction, I guess, is curiosity versus some deep insight or knowledge of the situation. Yeah.

[Kara Swisher]

So in an interview with the Columbia Journals Review, you said that one of the reasons you really like the Q and A format is because you're able to bring both reporting and opinion. Talk about that. The distinction for people who don't think about it that way.

[Isaac Chotiner]

Well, you know, I mean, I'm lucky enough to be able to do, you know, as are you, to do interviews where I don't think people are confused about what my opinion is on various subjects, you know, about the Trump administration or so on. And so I can ask questions that I think reflect, make it clear what my point of view is and not feel like that's violating the terms of the interview. But to get to a point where I'm asking those questions, it often requires a certain amount of reading or reporting or talking to other people about what those questions will be. And so I like the fact that I can kind of do sort of traditional, some at least traditional reporting things before an interview to sort of get my prep and then in the course of the interview, can put that to use and also do it in a way where I don't feel like I need to sort of hide what my opinion is in a way. Right. Which is great. In some ways, but can also feel stifling.

[Kara Swisher]

But talk about why opinion is important to you because it also puts you in a position of potentially coming up as partisan. I answer these questions all the time. I'm like, well, I think it's fair to the readers. Do you think it turns off readers or. I think it brings them in myself.

[Isaac Chotiner]

But, I mean, it's a good question. I don't know. I'm sure it turns off some people and brings in other people. You know, I just think that broadly speaking, allowing your own perspective to not sort of ask all these questions completely neutrally just allows for a broader range of questions and ways of asking the question, which I think makes for a more interesting interview.

[Kara Swisher]

Right, right. I mean, I think hiding a point of view has always been a mistake. Right. Jokingly, aside of fair and balance, there's no such thing. But at the same time, it doesn't mean you can't be fair if you don't. You know, I think Christiane Amanpour was, I think she said truthful, not neutral, essentially, which I thought was a pretty good way to figure it out. But when you're doing that, I think you get more trust. At the same time, when you do that with subjects, have they taken advantage of that from your point of view?

[Isaac Chotiner]

In what sense?

[Kara Swisher]

Meaning like, oh, you don't like Trump, and therefore you're not gonna listen to me, for example. He's a perfect person. That's a Rorschach test on everybody.

[Isaac Chotiner]

Oh, that's. Yeah, that's interesting. You know, not so much. I think, you know, people who would feel that way probably make that assumption before they start talking to me, just thinking, oh, he's, you know, working for the New Yorker or whatever else. I mean, I will say, you know, it's gotten. It's gotten harder and harder to get Republicans to talk in the 10 plus years I've been interviewing. And I think most of those reasons are not the fault of the media and are probably inevitable given the way politics is going. But. But there are other times where I think maybe if I had had fewer opinions about something in a previous interview, that maybe someone has seen that it would be easier to get this person to talk. And I regret it. But as I said, I think most of the reasons for that are way beyond one person or one news institution's ability to fix or change.

[Kara Swisher]

I agree with you on the Republicans. Some do, though. Some are. But you're right, they're harder to talk to and talk to in a normal way. But how do you convince them to come on then?

[Isaac Chotiner]

It's a good question. I mean, the truth is that the most people that I try to get to come on who don't, I'm not dealing with them, I'm dealing with their people. But just try and be honest and say you hope for a good conversation. The thing is that you can't promise things that you can't promise. You can't say things are going to be off limits. So there's a limited amount of things you can do. You can just say, I really think this would be an interesting conversation and I hope you'll just try and be sincere about would be easier if you could say, you know, we're not going to talk about X and then you talk about X. But we don't do that, so.

[Kara Swisher]

No, we don't either. Yeah, you know, it's. What's interesting is I try to reach the person themselves rather than their people. I don't like talking to the people most of the time or the initial outreach is to the person. I can find their phone number or whatever.

[Isaac Chotiner]

Yeah, no, it's great. I actually prefer text if possible. If you get a person's phone number, just. It feels more informal. Goes back to what we were talking about earlier.

[Kara Swisher]

So talk a little bit more about research. You've talked about how the main thing that makes a good interview is research. I agree with it and you do a lot of it. But another element of a good interview is the conversation between two people. And that means as an interviewer, you also have to be flexible. So how much time are you relying on questions you've written beforehand versus letting the conversation flow organically, even if it takes unexpected turns?

[Isaac Chotiner]

Well, I mean, yes, I don't actually write all my questions out beforehand. For most interviews I write. There are some times that I'm doing an interview that I'm worried, worried about how it's going to go or that, you know, go off the rails or I need to quote specific things to the person. And so I write out very specific questions. Other times I just have kind of notes in front of me with things I want to ask and some structure for the interview because I hope that the form the interview takes, like, you know, a story will have sort of a beginning, middle and an end. But I try and keep it flexible enough that I'm not just reading questions to them. Because for me that feels a little bit stifling. And my hope is that I've kind of done enough background work that I can feel comfortable talking without having to look at the questions. I will say there are some times where I'm doing a subject that I'm not a great expert in. A news event has just occurred, you know, some Supreme Court decision that I'm talking to a lawyer about. And just because I want to quote the decision accurately and I, you know, want to phrase things a certain way that I will write it all out, but. But it's not always the case.

[Kara Swisher]

Interesting. You don't have the script itself.

[Isaac Chotiner]

No, not usually, no.

[Kara Swisher]

Yeah, because you're probably listening actually for the next. For something interesting. I think a lot of people don't go off their, their scripts essentially, but you know, they won't. It's not really the follow up question because that's a sort of weird canard. Did you didn't ask a follow up question. Is that you're not listening in the first place in order to move forward?

[Isaac Chotiner]

Well, no, I mean I, I should say though, about the listening thing is obviously I try and pride myself on listening. Not just in my personal conversations with friends or whatever else, but also in interviews.

[Kara Swisher]

See, that's where I don't try to listen. But go ahead.

[Isaac Chotiner]

Oh, good, good, good. But when I. Whenever I'm typing up an interview, whenever I'm transcribing it, I'm always surprised that there are things that no matter how close I thought I was paying attention, there are things that I missed or nuances that I missed. And so that's one of the things I actually like about transcribing stuff, is that it makes you realize that they're, you know, you're paying attention. Less close than you think, or at least I am. Right.

[Kara Swisher]

That there's something that pops out into it. So Your Q&As for people don't know are printed. But you used to host a podcast for Slate called I have Talk about the pros and cons of written versus audio. And do you feel a push towards being forced back into audio?

[Isaac Chotiner]

I guess, you know, I haven't felt it yet, but maybe my expecting the phone call from my bosses at any moment.

[Kara Swisher]

Video is it?

[Isaac Chotiner]

Yeah, exactly. I haven't gotten the push yet, but you know, maybe it'll come. You know, I didn't love doing a podcast just cause, you know, going into a studio and the kind of extra stuff around it didn't particularly interest me. But I gather it's easier now even than when I was doing it six years ago. Yeah, but eight years ago, whatever it was. But I like that people can hear the conversation, that part of it is fun. I mean, the thing you do have to keep in mind is that it's. Or I always try and keep in mind is written words can be misleading.

[Kara Swisher]

Right.

[Isaac Chotiner]

People can give responses that when typed out, literally seem hostile when they're not.

[Podcast/Ad Narrator]

That's right.

[Isaac Chotiner]

People say things that don't make sense. Tone. Tone gets lost. People have weird phrases. People say. Yeah, no, like things like that. Which if written out. Yeah, no, doesn't make any sense. But you know what they mean when you're talking to them. So they're all, all these things are, you know, worth keeping in mind. And. But to me, that. That's an interesting part of the Q and A is how to. How to have as much of what we actually said while not being misleading in any way. And so that editing challenge I actually find quite interesting.

[Kara Swisher]

Do you ever feel it puts you on your back foot? Because a lot of people say, that's not what I said, it's not how I said it. Like when you put this stuff.

[Isaac Chotiner]

I haven't had that really happen. I mean, there was one guy who said that the interview was more or less fake, I think. But I guess that is always a concern. I mean, but again, it's one reason you have to have to tape the interviews, Right?

[Kara Swisher]

Exactly. So do you. Do you feel like you want to go into audio now that it's sort of the thing or video is really the thing now?

[Isaac Chotiner]

No, definitely not.

[Kara Swisher]

Definitely not. You're going to stay retro in that?

[Isaac Chotiner]

Well, I mean, I, you know, I don't know. It's got to make a living. So we'll see.

[Kara Swisher]

We'll be back in a minute.

[Sponsor Representative]

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[Podcast Host (Today Explained)]

Okay, so you may have heard New York City gets a new mayor this week. 34 year old Democratic Socialist Zoran Mamdani. Mamdani's election was one of the biggest wins for the left in 2025. But since then, he's been quietly going about a new task, trying to make sure his sweeping campaign promises can actually happen.

[Isaac Chotiner]

An agenda that will freeze the rents for more than 2 million rent stabilized tenants, make buses fast and free and deliver universal childcare across our city.

[Kara Swisher]

I'm a little skeptical about how he's gonna get everything done.

[Podcast/Ad Narrator]

I think that's what a lot of people are promised.

[Kara Swisher]

So many things like free buses, you know, housing and all that. Promises, promises.

[Podcast Host (Today Explained)]

Can this new kind of politics succeed? Or is this Madani's high point? The days before he gets into office? On this episode of Today Explained from Vox, we sit down with New York City's Mayor Electric and ask him directly, is he for real? That's this week on Today Explained.

[Kara Swisher]

So let's talk about your interviewing style just a little more. As I mentioned earlier, you had a reputation for being a tough interview in the fall. You had some contentious conversations with legal scholar Cass Sunstein and former White House press secretary Karine Jean Pierre. In Jean Pierre's case, that interview was called career ending and an absolute train wreck. I was sort of shocked by it. Talk about these interviews, how much do you follow the afterlife of say, the Karine Jean Pierre or Cass Sunstein in that case?

[Isaac Chotiner]

I did the Karine Jean Pierre because I guess people were interested in some media organizations, reached out for comment about stuff. And I guess I followed the afterlife of that in part because the same reason that I did the interview, which is that I was very interested in how and maybe this gets back to me being able to express my opinion. I was very interested in how the Biden people were reckoning with what has happened in the last year and what happened in the six months before the election. And so I was really interested in that as a subject, which is why I wanted to interview Karine Jean Pierre and why I read her book and decided to do it. So, yeah, no, I definitely followed that one.

[Kara Swisher]

So you You. You said your goal isn't to make people look foolish. What does it feel like when you do? Well, because that was a clear. In the case of Karine Jean Pierre, you made her look foolish, but she made herself look foolish. I'm sorry, let me be fair.

[Isaac Chotiner]

Yeah, I mean, I guess, you know, I guess I don't think of it as look foolish. I mean, the part of the Sunstein interview that maybe you're referring to or were alluding to is this part about Henry Kissinger, which came up at the end of the interview, and his friendship with Henry Kissinger.

[Kara Swisher]

Right.

[Isaac Chotiner]

And I don't think of it as that, like Cass Sunstein should look foolish. I thought of it as like, here's a guy who's written a book about liberalism, and Henry Kissinger is sort of the figure pre Trump that I think of as being, if you count his record in places other than America, one of the most illiberal figures in recent American history. And so I wanted to kind of. I wanted to talk about that and I wanted to sort of bring those two things together in the interview.

[Kara Swisher]

Right.

[Isaac Chotiner]

And it, again, it's not to make someone look foolish. It's just I felt that that was an important thing to bring up.

[Kara Swisher]

Right. That he had to square that circle.

[Isaac Chotiner]

Yeah, exactly.

[Kara Swisher]

You know, explain this.

[Isaac Chotiner]

And we all. We all have. We all have contradictions and we all have hypocrisies, and they can be uncomfortable to be pushed on, but they're often helpful to be pushed on, I think, not just intellectually in your personal life, whatever else, because I think it helps, you know, it's good for people to be aware of that since we all have it. And so I thought it was.

[Kara Swisher]

No, it's fair. Yeah, it's fair. You told, in fact, the Columbia Journal's review. If you're asking questions that are meant to highlight contradictions, you have to set it up early in the interview when you know, you have a guest where the interview could be contentious. How do you strategize around that and try to anticipate the ways an interviewee may dig themselves into a hole or try to dodge that line of questioning?

[Isaac Chotiner]

Yeah, I mean, you know, I think this gets to the question of gotcha questions, which is a phrase I don't like, because you don't either. Okay, good. I don't really know what a gotcha question is. If people have some hypocrisies or contradictions, then they can say, yeah, I'm a hypocrite, or they can say, yeah, that's A contradiction. Or they can explain it, or they can say, this is why. This is why. You're wrong about this. But for me, at least, I think highlighting those things is a really interesting way of looking at where people's blind spots are and also where kind of the blind spots of different intellectual traditions or political parties or whatever else is. And so I find that a really interesting thing to focus on, and I think it's important to try and set it up. I mean, I was thinking about this because I did an interview with the French political philosopher Bernard Henri Levy number of years ago, and he had written a bunch of stuff about women in the Islamic world and the lack of respect shown to them and why this was an important issue. And I wanted to talk about that. But also I wanted to talk about his support for some Frenchmen who'd been accused of sexual misconduct. I believe it was Roman Polanski and Dominique Strauss Kahn, if I remember correctly. And so the only way I could think to sort of set this up was asking the questions about women in the Islamic world and what he'd written about them early on and then bring up the Polanski stuff later on in the interview. And I do think that it has a gotcha feel.

[Kara Swisher]

Yes, a callback.

[Isaac Chotiner]

Yeah, exactly. But to me, I don't quite know a different way of going about that. And as I said, if he has a response, he's welcome to give it.

[Kara Swisher]

But to me, you could ask right after. I mean, the next question, after you set up the thing. Would you wait?

[Isaac Chotiner]

I waited. Yeah. I can't. I waited because I wanted the interview to kind of have a narrative arc to it, but, yeah, no, so I. I do think about those questions, but generally, I think gotcha questions are fine.

[Kara Swisher]

Yeah, I agree. I don't think they're unfair necessarily.

[Isaac Chotiner]

I mean, they're questions I wouldn't ask. There's some types of questions I do think are unfair, and I try to stay away from those.

[Kara Swisher]

Such as? Give me an example, you know, certain.

[Isaac Chotiner]

Types of personal questions, people's consensual sexual behavior. You know, I think that I would not ask someone to criticize their place of work or colleagues unless I thought that their place of work or colleagues was doing something, you know, quite horrible or, you know, unethical in some way. I wouldn't say, like, you know, I think so. And so writer at the New York Times is a bad writer. What do you have to say about that? To someone at the New York Times? It's like. Like they're not gonna criticize their colleague, nor should they, you know, so something like that. But broadly speaking, that's not what we're talking about, right?

[Kara Swisher]

No. You know, I have forever lived with I made Mark Zuckerberg sweat, for example, or I made him say dumb things about anti Semites. Right. Or Holocaust deniers specifically. People come back to it again and again. Do you feel that that overestimates this assassin idea? I find it tiresome. You know, you made him sweat. You almost made him faint. I'm like, I didn't. But he did sweat. I didn't make him sweat. You know, I mean, it's an interesting thing because it sticks with you. And I wouldn't say it's a bad thing necessarily because it makes people nervous in the beginning, I guess. I don't know.

[Isaac Chotiner]

Yeah, I mean, most people I interview don't know about me or my work or whatever else. Most people don't read bylines. And, you know, I think this is also one of the advantages maybe of doing print interviews rather than, you know, is that I think that, you know, people have more of a sense of who you are if you have a podcast or you have whatever else. And so I don't feel like I'm reckoning with that too often when it comes to actually doing interviews.

[Kara Swisher]

Oh, I think people know exactly who you are. I'm sorry, I think they do.

[Isaac Chotiner]

I think people in like journalism and stuff do.

[Kara Swisher]

Yeah, I think subjects do. I think your subjects, many of the people who work for your subjects certainly do, or PR people certainly do. So every episode we get a question from an outside expert. Here's yours.

[Podcast/Ad Narrator]

Hello, I'm Anna Sale. I'm an interviewer, the host of Death, Sex and Money. And on our show I'm often talking to people about things that they haven't talked about at length before with interviewers. And I think of you, Isaac, as someone who is particularly gifted at getting public people, public figures, to talk about things in ways maybe they didn't intend. And I have some questions for you about that. One is just if you approach interviews, thinking of that as a goal to pierce the self presentation of public people for your readers, I also wonder if that's more fun for you when you don't necessarily feel aligned or don't really like the person you're interviewing, if that makes you, you think, a more incisive interviewer, more skeptical interviewer, and thus you get a better interview.

[Kara Swisher]

Thanks.

[Isaac Chotiner]

Yeah, it's a good question. I definitely feel like when I'm talking to public figures or politicians that What I want to do is get them to say some things that they haven't said a million times before.

[Kara Swisher]

Right.

[Isaac Chotiner]

One helpful way of doing that is to look at previous interviews that they've given and think like, where would I have tried to ask a follow up that the interviewer didn't? And you know, same is true for my interviews. Whenever I read them, I think, oh, I should have asked this follow up. And I, you know, I forgot to or I didn't. So that's absolutely a goal is to try and get people who I feel like sometimes I'll be thinking during an interview like I don't actually say this to people, but sometimes I'll be thinking during an interview like, you know, if you just repeat the same talking point for six times in a row, we're just going to cut it. So why are you even telling me this? You know, we've heard this five other times in the interview. So.

[Kara Swisher]

See, I do say that. I say that out loud. Go ahead.

[Isaac Chotiner]

So yeah, that's definitely a goal is.

[Kara Swisher]

To get them off of these talking points.

[Isaac Chotiner]

Yeah.

[Kara Swisher]

And what about the. Besides piercing the self presentation, which is talking points, I think that's what she's talking about. Is it easier when you're not aligned with them or is it harder when you are aligned with them?

[Isaac Chotiner]

Oh, you know, I mean, I guess you could say that unconsciously people you're aligned with, you're probably less aware that they're saying talking points because it's something you agree with. So it seems less propagandistic or whatever else. So I think that, I think that's absolutely something that if you're, if you're more aligned with someone that you're talking to or you think you are, that it's definitely worth trying to remind yourself that, you know, that you may be not paying as close attention as you should to them being propagandistic or saying talking points or whatever else.

[Kara Swisher]

Anna had a second question too. She wanted to know if you have any ridiculous stories of being iced out or intimidated by someone you interviewed or their publicist for including something they wanted taken out in an interview. That's happened to me innumerable times and I've said no. Unless it's factually inaccurate.

[Isaac Chotiner]

Yeah, you mean I'm trying to think about like I'm sure there are stories. I mean, the most, the most intimidated I ever was in an interview was I interviewed the novelist Vs Naipaul at his house in London and he was, this was pretty early in my interviewing career and he Was quite bullying of me. And, you know, I think it actually made for a pretty good interview that he. Because his personality in bullying me the way he kind of did, everyone came across. But. And in fact, I've often thought that, you know, if I had been 10 years older, I might have have been less bullied, which may have actually made for a less good interview in that case.

[Kara Swisher]

Interesting. Yeah.

[Isaac Chotiner]

Yeah. But that was the most kind of intimidated I'd ever been in or have ever been.

[Kara Swisher]

What did he do to bully you?

[Isaac Chotiner]

Oh, I mean, he was just, you know, he's a very grumpy guy and he would just. He would just say, like, this is a silly question, you know.

[Kara Swisher]

Yeah, that trick.

[Isaac Chotiner]

Answer a question with it, you know, nothing, I think nothing about this, you know, that sort of thing. Which for me, and as someone who I got all of his books right behind me on the shelf, looked up to him a lot and still do as a writer, not as a person. That was definitely hard.

[Kara Swisher]

Well, it can also be incisive. I mean, one of the. I just had an experience with Kamala Harris where we were joking about something backstage about Robert Kennedy Jr. And circumcision and autism. The link. He was making a link which is not there. And it was so weird. It was like, huh, that's so fucking strange. And then when I got on stage and mentioned it, because it had just been in the news, right. And she looked at me dead and said, this is nothing to laugh about. And she had just laughed about it. And then she went into this sort of high handed kind of thing where she was like yelling at me for like even asking the question. I was like, I'm gonna kill you. I literally can't believe you just did that. Which was interesting. And I thought I was. It was a real insight, actually.

[Isaac Chotiner]

I sometimes get the sense that she doesn't realize her political career is over.

[Kara Swisher]

I don't know. Yeah, it was so funny. I was like, where's the person backstage who just had a very insightful comment about this? Like, it was really an interesting.

[Isaac Chotiner]

Well, perhaps telling about her electoral performance.

[Kara Swisher]

Yeah, I was like, be the person backstage because that's the person who gave a great answer. Actually, one of the things you also do, which I think is interesting, is you summarize what your guests are saying or ask if the summary is accurate, which I think is a power play, actually. You use phrases like, I'm trying to understand. What specifically do you mean? Is that strategic? Because I think it's very. When I read it, it's very Funny, it forces you to have your interviewee say what you're. What they're saying is accurate and not go back on that. It seems like. But maybe you're not doing that.

[Isaac Chotiner]

Yeah, no, I think I. I think I probably am doing that sometimes. I am doing that to sort of get them to sort of say up front what it seems to me that they're hinting at or. Or suggesting, because sometimes they don't want to say it up front. I should also say, you know, it's also to go back to the thing about listening to other people. It's like when the interview's listening to the other person, but you're also thinking about what. How much time is left and what else you have to ask. And you're also thinking about, you know, you're thinking about these other things, about the context of the interview. So sometimes you don't feel like you actually got. Exactly. And you want to be clear. And so that's. That's often the case too. Maybe I'm telling on myself by saying that, you know, I want to, you know, not totally sure what the other person said, but because you're often. You're trying to do a million things at once, that's. That's definitely the case.

[Kara Swisher]

Do you ever decide it's time to back off, either because your guest clearly doesn't have a good answer, or you need to move on, or they're getting upset. Do you get rattled by that? I do not. I don't mind them getting upset in front of me or being upset or being rude back at me.

[Isaac Chotiner]

I don't mind rudeness. Am I trying to think like that's.

[Kara Swisher]

A dumb question that drives me crazy? That makes me double down?

[Isaac Chotiner]

Oh, no, no. I, you know, this goes again. I think if more stuff was in person, it might shake me more, but over the phone, it doesn't really. Most of the time, these interviews are not particularly. I mean, the two you brought up, Cass Sunstein and Karine Jean Pierre, I think Karine Jean Pierre felt that, you know, she and I were not seeing eye to eye about some of the things she was saying. But the interview didn't feel tense, and neither did the Cass Sunstein one at all.

[Kara Swisher]

So, you know, I think tense.

[Isaac Chotiner]

It's interesting. I mean, I sometimes think the interviews read more tense than they are, or sometimes maybe it's that I just have more of a tolerance for being uncomfortable in a phone conversation than other people. They don't feel that way to me usually even when they read that way. So you know, I don't know. It's a good question. I should think more about that.

[Kara Swisher]

Are you ever surprised when that if you didn't think that was a tense one and then everyone was like, oh my God.

[Isaac Chotiner]

Well, no, I guess what I mean is that like, it's like, you know, you could get into a debate with someone and, you know, then shake hands afterwards and it doesn't feel tense. And sometimes it does. And I guess just sometimes like Karine Jean Pierre, I thought she was very polite answering the questions. And even though I was. Was asking somewhat aggressive questions, it just. There have been interviews that I've done that did actually feel tense.

[Kara Swisher]

Like who?

[Isaac Chotiner]

Newt Gingrich once when I interviewed him.

[Kara Swisher]

He's a pain in the ass.

[Isaac Chotiner]

Yeah, a couple kind of Trumpish people. One thing about what's happening in the world now with Trump and what's happening in the country is, in my opinion, it's all these things. It's horrific and it's depressing and so on, but it's also ridiculous. And a lot of the people defending him in public are ridiculous. And there's only so much you can do about this that's dead serious where, you know, it's like arguing that the earth is flat. And so I try and sometimes those interviews that I feel like would be more tense with those types of people to try and make them funny or tongue in cheek, whatever, because, you know, as I said, there's only so much you can get at pounding the ground.

[Kara Swisher]

Right. You don't want to take the flat earth thing seriously, is what you're saying.

[Isaac Chotiner]

Well, I'm not even saying that. It's like, it's more just that, like, like it's just not that interesting to read people arguing about whether the earth is flat. And there's something so absurd about it.

[Kara Swisher]

We'll be back in a minute. So you also have a reputation of being quite critical of other journalists on social media, which I completely endorse. I agree that you journalists should be more critical of each other. They sometimes tend not to. But you were in a fight on X with Semaphore's Ben Smith, who is disputational person over the outlet's coverage of the Saudi Crown prince on the outlet's Gulf vertical. You wrote on X, quote, you would have to be brain dead to read this piece, not immediately wonder who's funding Semaphore. Gulf Sri Myth criticized you for the insinuation the post was sponsored content. I'm with you on that one. I've had that argument with him off screen. Talk about why you do this. I often get into fights with reporters sometimes. What are you hoping to highlight there? Just the obvious.

[Isaac Chotiner]

You mean why I like, will criticize other reporters? Sometimes, yeah. Geez. It's a good question. You know, sometimes it's probably just being dumb, but it kind of. It's a way of engaging with the world. I don't know, it's probably too critical. Too critical a way of engaging with the world, but it's a way I kind of engage with the world. And because, you know, maybe my pop. Psychological explanation of this would be that, you know, media tends to listen to other media criticism. I feel like. Whereas, I mean, I wouldn't do this for various reasons, but I could tweet out that I'm upset about what's happening in Sudan or Gaza or wherever else, Ukraine, and nobody cares. Nobody's paying attention. It feels like with journalists, they pay attention to what other journalists say. And I hope, certainly I take criticism from other journalists and know take it seriously and hopefully other journalists do too. So maybe it's a way of feeling like you can actually be heard in a way that you can't in other ways.

[Kara Swisher]

Yeah, possibly. Possibly.

[Isaac Chotiner]

There's also, and this is not a. This is not about the Ben Smith stuff. There's just, you know, there's a lot of terrible journalism out there and seems worth paying attention to, pointing out. Making it better.

[Kara Swisher]

Yeah, yeah.

[Isaac Chotiner]

You know, part of the reason you get into media is because you're interested in engaging with it and you're, you're, you want it to be good. And, you know, we all have like, our mini dramas with the newspapers and magazines we've been reading for 25 years and we want them to be better and we love them and whatever else, so.

[Kara Swisher]

Journalists face a lot of challenge, though, when it comes to access right now. It's absolutely true. As you noted, politicians and other powerful people can choose to sit down with friendly media outlets, which they're doing like, extremely. Or else they don't need it at all. Like there it's direct. Direct to customer, essentially. Do you think that is just. That's gonna be the case all the time, that they'll find their friendlies and the people will just do it by themselves or edit things out. Does that make it more difficult to land these interviews in this climate? How do you hold power people account when they're competing against influencers and these partisan outlets? Because it's a lot easier for them to do that, essentially.

[Isaac Chotiner]

Yeah. I mean, I, you know, I Wish I had a good answer. I'm not optimistic about it.

[Kara Swisher]

Meaning?

[Isaac Chotiner]

Oh, I mean, I think what you said is accurate. And it's going to be harder and harder to get access. And, you know, that I think, is a real problem.

[Kara Swisher]

Who have you recently gone for that you haven't been able to get? Marjorie Taylor Greene, in our case.

[Isaac Chotiner]

Oh, interesting.

[Kara Swisher]

I think she doesn't want, because I've said explicitly I'm gonna ask her about the other things. Like, I agree with her on a couple of things, but let's ask about trans again. Let's ask about this. And I'm sure the PR people have heard it, me say it. Like, why isn't anyone asking about the other 93 things she has heinous opinions on? Like, because she happens to be reasonable about five, you know, that we can all agree with, which seem to be the lowest bar of all time. You know, I appreciate her doing them, but at the same time, it doesn't negate all the other things she said. Essentially.

[Isaac Chotiner]

Right. Yeah. No, I mean, I've, you know, I was just going through a bunch of Republican senators who I'd been trying to get at various times and haven't had any luck with that. And I mean, I've stopped trying as much, as much as I used to, just because it's just so hard to get Republican politicians.

[Kara Swisher]

Who would you love to get, for example? Who have you not been able to get?

[Isaac Chotiner]

Well, Kissinger died. He was number one on my list.

[Kara Swisher]

You could still do that interview?

[Isaac Chotiner]

I could, I could talk to the corpse. Talk to the corpse? Yeah. Narendra Modi is someone who I've tried to get for a long time. Not going to happen. Tony Blair is one you're not missing much. Fair. You know, so, yeah, there, there have been, I'm trying to think, though, who else? I, I, I was able to interview Imran Khan, the former prime Minister of Pakistan. So that was, that was, that was interesting. He was on my list. People I really wanted to talk to. I don't know. Sean Connery's dead. My list is quickly getting smaller. Right.

[Kara Swisher]

Is there anybody that you, Your number one person? People always ask me.

[Isaac Chotiner]

I think Modi would be number one.

[Kara Swisher]

Really? Why, why Modi?

[Isaac Chotiner]

I just, you know, I'm very interested in India, travel there a lot and written about it some. And so he's always interested me.

[Kara Swisher]

Gosh, mine is Dolly Parton and Taylor Swift together, but. Okay, well, you know, together only talking about business. Nothing else.

[Isaac Chotiner]

Else.

[Kara Swisher]

Nothing else. Because I think they're business people. I Think we don't talk about their business acumen as much as we talk about their songs.

[Isaac Chotiner]

Yeah, that's interesting. I don't know anything about either one of them, I'm sorry to say.

[Kara Swisher]

That's okay. That's all right. You'll probably get them before I will. So. Journalists are under a ton of pressure from executives who are looking to appease the Trump administration. Right now. There's example after example. Last month, CBS newsletter in chief Barry Weiss spiked a 60 minute segment on Venezuelan deportees who were sent to a maximum security prison in El Salvador. Weiss defended her decision, denied politics played a role, saying she wanted to improve the piece. Some of her suggestions were fine, I don't think necessary, but fine. But the timing was certainly odd and she changed her opinion in the middle of it. Right. CBS is owned by Paramount, which is owned by David Ellison. He and his father Larry are currently trying to buy Warner Brothers Discovery, which owns cnn. Any deal would need regulatory approval. They have touted the fact that they will be able to get it easily, publicly and quite officiously, I think. Talk about those pressures right now and what worries you most. I assume you've never had that pressure. I have. Not that I can think of. Even working for Rupert Murdoch. Talk a little bit about what the moment is right now.

[Isaac Chotiner]

Yeah, I mean, I'm fortunate to not have had those pressures either. When I worked at the New Republic, we had a owner who was crazy and bigoted and, and Marty Peretz was his name, and not a very nice guy. And so there were pressures that came down, but it wasn't of the sort that you're referring to. Yeah, it's really bleak and depressing times. And I think that the Trump White House has very smartly understood that the way to sort of exert some pressure on the media is not to, you know, not to do what he did in his first term, which is just sort of berate people, but to you know, make regulatory approvals conditional on, you know, kissing the ring or whatever else. And I think that that's definitely very scary and, yeah, depressing. I, you know, I, I, I wish I had something more interesting to say about it. I mean, it's, it's, it's, it's bleak and, you know, quite worrisome.

[Kara Swisher]

If that was presented to you, if you were, were Sharon Alphonse, for example, what would you do? She wrote a really terrific memo, obviously.

[Isaac Chotiner]

Yeah, I mean, I, I think it's incumbent on journalists if they feel that they are being censored for political reasons. To, you know, essentially go public with it. I mean, without specifically weighing in on exactly, you know, what we know and don't know about that situation. I mean, I think there's a broad matter that's absolutely, that's absolutely the way to, to go about it is to sort of go public.

[Kara Swisher]

So in that controversy, because it's the most recent, which one of the people would you want to interview?

[Isaac Chotiner]

Oh, I mean, Alfonsi, probably less than Barry Weiss or David Ellison, but just because I feel like Alfonsi's perspective is clear. But yeah, Barry Weiss or David Ellison? I mean, David Ellison, I think, is a very interesting figure and would definitely enjoy interviewing him.

[Kara Swisher]

See, I would pick Larry Ellison because he's the smart one.

[Isaac Chotiner]

Yeah, I was about to say Larry, actually, I should have. That. That would have been a good answer. He's. He, he does the dying as goatee thing, which I find interesting.

[Kara Swisher]

Yeah, he's a character. I've interviewed him many times, but he's the one. He's the brains of the operation, as far as I can tell.

[Isaac Chotiner]

And do you, do you, do you perceive that he has actual deep interest in Paramount acquiring Warner Brothers? Or do you feel like you don't?

[Kara Swisher]

I was actually out with a bunch of people last night and we all know him really well and we're sort of surprised that he's continuing. Cause it's such a nothing business for him, for someone like him. And so I think he's trying to please his son. I don't even know. I'd have to ask him. I'd love to know, like, why?

[Isaac Chotiner]

Well, yeah, I mean, this is something that, you know, maybe one of my colleagues at the magazine will do, but a sort of profile of that father son dynamic seems psychologically rich to say the least.

[Kara Swisher]

Yes, absolutely. I just. It's so dumb for him. Like, this is a dumb deal and it's dumb after. If he gets it, it's dumb. And so, so, like he never does dumb things, really. And so you're like, why are you doing this dumb thing? So that's who I would interview.

[Isaac Chotiner]

It's a good answer. Yeah.

[Kara Swisher]

I want to end by looking at some of the big stories coming in the new year in 2025. You wrote a lot about the Middle east and the war in Gaza between Israel and Hamas. And Trump recently met with Israeli Prime Minister Benjamin Netanyahu to talk more about the war in Gaza, Syria, Iran and more. Officially, a ceasefire with Hamas is holding, but both sides of it accused other of violating it. Negotiations around the second phase have stalled. And Trump and Netanyahu are reportedly at odds over what happens next, although they affirmed their bond during this latest meeting. Where do you see that relationship heading in the next year and what could it mean for the ongoing conflict in Gaza? And who would you think is important to talk to for this?

[Isaac Chotiner]

Yeah, I mean, there is going to be an election in Israel later in this year, so that will be interesting. Which is an important election for Netanyahu, who variety of reasons having to do with his corruption trial and political legacy and so on. In terms of that relationship, I thought that what happened at the White House was indicative of it in the sense that Trump has shown a willingness to push Netanyahu and the Israelis in short term ways, especially earlier in 2025 about coming to some sort of ceasefire in Gaza, even though, as you say, it hasn't exactly held. It's held in some ways, but certainly not in others. People are still dying. To me, what that sort of showed was that I think Netanyahu, and I think this is true of Putin to some extent too correctly perceives that.

[Kara Swisher]

He.

[Isaac Chotiner]

Can sort of make somewhat of an effort to act as if he is going to do what Trump wants, but there's never quite enough follow through. And so Netanyahu can sort of keep getting what he wants from Trump, which I assume is continuation of the American Israeli relationship, support for Netanyahu politically and dragging his feet on any sort of long term solution in Gaza. And like I said, I think Putin correctly perceives that this is the case too, that he can sort of make noises about peace or call Trump once every few weeks and therefore keep up the pressure on the Ukrainians without having to truly commit to a peace deal. And so I think this is a smart way to deal with Trump in both cases. And I think it's what we'll sort of continue to see some version of the status quo dragging on and on and on.

[Kara Swisher]

And who do you think an important interview during this time is, if they would do it? What would be the most important to you?

[Isaac Chotiner]

Well, you know, I mean, maybe this gets to what we're a version of what we were talking about earlier. I don't know if this is a great answer, but I'm just more interested in terms of just to mention Ukraine and Gaza, two ongoing conflicts. I'm less interested about White House decision making and talking to the principals there than I think I would have been. I think part of the reason I've been interested in talking to Biden people in the last year about Gaza policy is that it felt their policy, which left a lot to be desired, in my opinion. It was interesting to talk through how they were thinking about it in a way that I just sort of. I want to read investigative stories. Like I want to read investigative stories about the Trump administration's business deals in the Middle east or Steve Witkoff's business deals in Eastern Europe. I'm less interested in sort of hearing from principals, you know, talking to Marco Rubio about how he's thinking about Gaza. That sort of interview in the Trump administration just feels completely null and uninteresting to me.

[Kara Swisher]

Yeah. Although I think Witkoff would be interesting.

[Isaac Chotiner]

Wyckoff would be interesting. Witkoff would be interesting.

[Kara Swisher]

Here's why is he dumb? He seems dumb. So I'd like to know. That's like, I'd like to talk to him to find out out, like, essentially, how dumb is he? Because that's what you get from people or a Lutnik. Is he a moron? Because people say moron to me a lot when talking about his friends, actually, which I'm most.

[Isaac Chotiner]

I find this with all conversations. The reason I want to talk to people is to find out if they're dumb.

[Kara Swisher]

They're dumb. So far, you're smart. So next year is also an election year within the Democratic Party. There are primaries pitting more establishment candidates against progressives. I'm thinking of Senate primaries in Maine, Michigan and Minnesota. There's a lot of issues that Democrats have not resolved that divided them in the wake of the. The 2024 election. Is there areas you're interested in probing with the Democrats?

[Isaac Chotiner]

Yeah, absolutely. You know, I'm interested in kind of this generational and ideological divide that seems to be showing up or will show up in certain primaries. Maine and Senate race being an example of that. Obviously, some of these questions showed up in the New York mayoral election. And I'm just interested in broader questions about, you know, where the Democrats should be going, what is the right political strategy, how they're going to go about winning races in purple or red states for the Senate, which they're going to have to start doing if they want to ever get the Senate back. I think my gut feeling is that these issues are kind of going to be largely papered over in 2026 because it's an off year election and the president's party usually suffers defeats and that Democrats, whatever they do, are probably going to have a pretty good election. But I think for the 2028 primary, these issues will certainly come to the fore in a more kind of urgent way.

[Kara Swisher]

Is there anyone you're very intrigued by at this moment? I just have to talk to this person.

[Isaac Chotiner]

Oh, God. You keep asking me if there's anyone I feel like I have to talk to, and I realize I don't have good answers for these questions. Most of the. Most of the people I consider lead the leading candidates for the Democratic nomination. If you were just to look at the, like, Vegas odds for. I think they're all pretty. Pretty interesting as possible interview, you know, Gavin Newsom, Josh Shapiro, Ocasio, Cortez, whoever, you know, these people. I think all of them are pretty interesting, actually.

[Kara Swisher]

Have you interviewed Gavin Newsom?

[Isaac Chotiner]

No.

[Kara Swisher]

He would be good with Gavin News. I'd read the hell out of that.

[Isaac Chotiner]

I'll tell you, my colleague Tad Friend wrote a profile of him in 2018, I think, for the New Yorker, which I think of as, like, one of the, like, most brutal pieces I've ever read.

[Kara Swisher]

It is. He's a complex person. Person. Yeah, he's a. He's very interesting, though, I'll tell you that. I always tell him he's really interesting for a handsome person. Often they aren't as interesting as less handsome people, but he is very handsome and very interesting. There's many more big stories from 2025 that will carry over into the year. You mentioned Russia's war in Ukraine. As is recording, there's no peace deal, despite some recent activity. There's also the AI race in China, Trump's expansion of presidential authority, political violence, escalating tensions with Venezuela, a grueling civil war ensu Sudan, obviously the end of Trump himself. It's moving in that direction very clearly. What are the big questions you have heading into 2026?

[Isaac Chotiner]

I mean, I would say that Ukraine and Gaza are two things, but beyond that, I think. Yeah, you know, we touched on this earlier about the question of what's going to happen, you know, is the next president going to. He's going to be making regulatory decisions based on, you know, how much people come and kiss up to him. Just, you know, where the country's headed is seems like, you know, in some ways the big question, and that's a question of where the Republican Party's headed. And, you know, I think the kind of question, at least in my mind, that hangs over kind of everything, I feel like I think about this in some version, you know, every 20 minutes is like, once Trump is no longer on the scene or once he's no longer president, like, is the country going to revert to some sort of normalcy in whatever that meant pre Trump, and I don't know the answer, but there's so many ways in which I think about that, and it's also related to the question of just. Trump is certainly unique in most ways, but there are similar politicians or politicians with similar kind of ideological affiliations winning across the globe, and how much is that sort of a permanent thing or not? So I think those two questions, I think, definitely interests me. It's something I've talked a lot about in interviews, done a lot of interviews about. And so I think that that sort of hangs over most of most of the intellectual questions I have about where we're headed.

[Kara Swisher]

What next? Is what you're essentially saying. Yeah, what next? So that sort of last question, you're doing the exit interview, Trump, he picks you. What would be your first or your last question for him? You get to pick.

[Isaac Chotiner]

Well, you know. You know, I'll just say I don't know, but I will answer that question by saying I've often thought about what I would do if I interviewed Trump, and I don't know what I would do, but I think the one thing that I thought of would be interesting is just to choose one small subject and just ask him a million questions about that subject, whether it would sort of be like, Trump and race or Trump and women or Trump and his parents, and just to sort of. Of. Just to sort of go on one specific thing and to steer clear of what was in the news that day or whatever else, and hope that by kind of nailing down, you could get something and focus him in a way by asking the same question about the same subject. Because I think that there's something about the kind of sort of. What's the words I'm looking for? Sort of hyper. There's so many questions, and you're asking him so many questions, and he's switching subjects all the time. Anyway, this probably would not work. I'm almost sure it would not work, but it was the only. Only idea I had for how to make a Trump interview interesting.

[Kara Swisher]

That's a good one. Yeah. Drill down on one thing. I think I would. My first question would be, did your parents hug you enough?

[Isaac Chotiner]

Yeah, it's a. It's definitely, definitely a question.

[Kara Swisher]

It would freak out. It would set him. It unsettled him right away. Actually, I'm gonna ask one last question. Tell me something personal about yourself that people don't know.

[Isaac Chotiner]

Okay. A big Houston Rockets fan, and. Yeah, sorry about that one. But, no, I'm a big Houston Rockets fan and very, you know, very anxious fan. Don't handle my emotions well about it. So. Yeah.

[Kara Swisher]

Okay. Well, we'll start with that next time. Yeah, next time. I appreciate it. All right, Isaac, thank you. I really appreciate your time and I'm excited to read your interviews over the next year.

[Isaac Chotiner]

Yeah, that was so much fun.

[Kara Swisher]

Today's show was produced by Christian Castro, Russell Michelle Aloy, Megan Burney, and Kaylin Lynch. Nishat Kurwa is Vox Media's executive producer of podcasts. Special thanks to Sheena Ozaki, Bradley Sylvester and Madeline LaPlante Dubie Steve Bone engineered this episode and our theme music is by Track and academics. If you're already following the show, you're an interview assassin. If not, you're on your talking points. Get off of them. Go wherever you listen to podcasts, search for on with Kara Swisher and hit follow. Thanks for listening to on with Kara Swisher from Podium Media, New York Magazine, the Vox Media Podcast Network, and us. We'll be back on Thursday with more.