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

18:11Interesting. You don't have the script itself.

18:13Kara Swisher:No. Not usually, no. Yeah, because you're probably listening, actually, for something interesting. I think a lot of people don't go off their scripts, essentially. It's not really the follow-up question because that's a sort of weird canard that you didn't ask a follow-up question is that you're not listening in the first place in order to move forward. Well, no, I mean, 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. See, that's where I don't try to listen, but go ahead.

18:43Oh, good, good, good. But 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 you're paying attention less close than you think, or at least I am.

19:06Kara Swisher:Right, that there's something that pops out into it. So your Q &As, for people who don't know, are printed, but you used to host a podcast for Slate called I Have to Ask. Talk about the pros and cons of written versus audio. And do you feel a push towards being forced back into audio, I guess? You know, I haven't felt it yet, but maybe I'm expecting the phone call from my bosses at any moment. Video, is it? 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 because, you know, going into a studio and the kind of extra stuff around it didn't particularly interest me.

19:43But 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, you know, 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. People can give responses that if – when typed out literally seem hostile when they're not. That's right. They can – people say things that don't make – tone. Tone gets lost. Yeah. People have weird phrases. People say, yeah, no, like things like that, which if written out, yeah, no, doesn't make any sense.

20:24Right. But you know what they mean when you're talking to them. So all these things are worth keeping in mind. But to me, that's an interesting part of the Q &A is 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.

20:42Kara 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. 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, exactly. So 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? No, definitely not. Definitely not. You're going to stay retro in that. Well, I mean, I don't know.

21:12Got to make a living. So we'll see.

21:17Kara Swisher:We'll be back in a minute.

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23:12Kara Swisher:Hi, everyone. It's Kara Swisher. I'm excited to put something new on your radar from the Vox Media Podcast Network. It's called Project Swagger with the one and only Robin Arzon, and it's all about helping you trust yourself, level up your mindset, and actually make the changes you've been thinking about. Robin is Peloton's Vice President of Fitness Programming and Head Instructor. She's also a 27-time marathon and ultramarathon runner, founder of Swagger Society Media Company, and a two-time New York Times bestselling author. In under 30 minutes, Robin shares the rituals, routines, and mental shifts that fuel her hustle and show you how to apply them in your own life.

23:52Kara Swisher:In the very first episode, she opens up about the moment that forced her to transform her inner voice and the strategies that helped her become what she calls a self-talk ninja. You can find Project Swagger with Robin Arzon on YouTube or wherever you get your podcasts. New episodes drop every Tuesday. day. 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 Corrine Jean-Pierre. In Jean-Pierre's case, that interview was called career ending and an absolute train wreck.

24:30Kara Swisher:I was sort of shocked by it. Talk about these interviews. How much do you follow the afterlife of, say, the Corrine Jean-Pierre or Cass Sunstein? In that case, I did the Corrine 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 I the same reason that I did the interview, which is that I was very interested in how and maybe this gets back to, you know, 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.

25:12And 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.

25:19Kara Swisher:So you said your goal isn't to make people look foolish. What does it feel like when you do? 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. Yeah. I mean, I guess, 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 we're alluding to is this part about Henry Kissinger which came up at the end of the interview and his friendship with Henry Kissinger. 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.

26:04And 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. And again, it's not to make someone look foolish. It's just I felt that that was an important thing to bring up. Right. Then he had to square that circle. Yeah, exactly.

26:19Kara Swisher:You know, explain this. And 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 – 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 interview may dig themselves into a hole or try to dodge that line of questioning?

27:01Yeah. 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 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.

27:40And 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 Lévy a 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 want to talk about his support for some Frenchmen who had been accused of sexual misconduct. I believe it was Roman Polanski and Dominique Strauss-Kahn, if I remember correctly.

28:22And 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. Yes, a callback. 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. Right.

28:49Kara Swisher:You could ask right after. I mean the next question after you set up the thing, which you waited. I waited. Yeah. I waited because I wanted the interview to kind of have a narrative arc to it. But yeah, no. So I do think about those questions. But generally, I think gotcha questions are fine. Yeah, I agree. I don't think they're unfair necessarily. I mean there are questions I wouldn't ask. There are some types of questions I do think are unfair and I try to stay away from those. Such as? Give me an example. You know, certain 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.

29:41I 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 they're not going to criticize their colleague, nor should they. You know, so something like that. But broadly speaking, that's not what we're talking about.

29:56Kara Swisher:Right. 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 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.

30:33Yeah, I mean, most people I interview don't know about me or my work or whatever else. Most people don't read bylines and I think this is also one of the advantages maybe of doing print interviews rather than – is that I think that 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.

30:58Kara Swisher:No, I think people know exactly who you are. I'm sorry. I think they do. I think people in like journalism and stuff do. Yeah, I think subjects do. Yeah. I think 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. 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.

31:42Kara Swisher: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 think a more incisive interviewer, more skeptical interviewer, and thus you get a better interview. Thanks. 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.

32:27And 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. Same is true for my interviews. Whenever I read them, I think, oh, I should have asked this follow-up and 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 if you just repeat the same talking point for six times in a row, we're just going to cut it.

32:57So why are you even telling me this? You know, we've heard this five other times in the interview.

33:00Kara Swisher:So I do say that. I say that out loud. There you go. Go ahead. So, yeah, that's definitely a goal. Is to get them off of these talking points. Yeah. 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? 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.

33:32So 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.

33:49Kara 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. it. Yeah. You mean, I'm trying to think about like, I'm sure there are stories. I mean, the most, the most, the most intimidated I ever was in an interview was I interviewed the novelist V.S. Naipaul at his house in London. And he was, this was pretty early in my interviewing career.

34:18And he was quite bullying of me. And, you know, I think it actually made for a pretty good interview that he, because his personality and bullying me the way he kind of did everyone came across. But, and in fact, I've often thought that, you know, if I'd been 10 years older, I might have been less bullied, which may have actually made for a less good interview in that case. Bully was interesting. Yeah. Yeah. But that was the most kind of intimidated I'd ever been or have ever been. What did he do to bully you? 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, or he'd answer a question with, you know, nothing.

34:55I think nothing about this, you know, that sort of thing, which for me, and as someone who looked up to him, 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.

35:11Kara Swisher:Well, it can also be incisive. I mean, I just have 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, oh 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 i sometimes get the sense that she doesn't realize her political career is over I don't know.

35:59Yeah, yeah.

36:00Kara Swisher: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— Perhaps telling about her electoral performance. 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.

36:35Kara Swisher:It forces you to have your interviewee say what they're saying is accurate and not go back on that, it seems like. But maybe you're not doing that. Yeah, no, 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 suggesting. because sometimes they don't want to say it up front. I should also say it's also to go back to the thing about listening to other people. It's like when the interview is going on, you're listening to the other person, but you're also thinking about how much time is left and what else you have to ask.

37:08And you're also 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 often the case too. Maybe I'm telling on myself by saying that I want to – 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 definitely the case.

37:29Kara 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. I don't mind rudeness. Am I trying to think – Like that's a dumb question. Like that drives me crazy. That makes me double down. 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 Corrine Jean-Pierre.

38:07I think Corrine Jean-Pierre felt that 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. So, you know, I think 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.

38:39Kara Swisher:Are you ever surprised when that if you didn't think that was a tense one and then everyone was like, oh, my fucking God. 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 asking somewhat aggressive questions, it just it didn't it didn't read. There have been interviews that I've done that did actually feel tense. Like who?

39:06Newt Gingrich once when I interviewed him. Oh, that's a pain in the ass. 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, you know, 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 it pounding the ground.

39:50Kara Swisher:Right. You don't want to take the flat earth thing seriously is what you're saying. I'm not even saying that. It's like it's more just that 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. We'll be back in a minute.

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42:14Kara Swisher:So you also have a reputation of being quite critical of other journalists on social media, which I completely endorse. I agree that 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 a disputatious person over the outlet's coverage of the Saudi crown prince on the outlet's Gulf Vertical. He wrote on X, quote, you would have to be brain dead to read this piece and not immediately wonder who is funding Semaphore Gulf. Smith criticized you for the insinuation the post was sponsored content. I'm with you on that one.

42:45Kara Swisher: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? You mean why I like will criticize other reporters sometimes? Yeah. Jeez. That'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 maybe my pop psychological explanation of this would be that media tends to listen to other media criticism I feel like whereas – I mean I wouldn't do this for various reasons.

43:30But I could tweet out that I'm upset about what's happening in Sudan or Gaza or wherever else, Ukraine and nobody cares. Nobody is paying attention. And it feels like, you know, with journalists, they pay attention to what other journalists say. And I hope, you know, certainly I take criticism from other journalists and, you 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.

43:56Kara Swisher:Yeah, possibly. Possibly. There's also, and this is not about the Ben Smith stuff. There's just, you know, there's a lot of terrible journalism out there and it seems worth paying attention to. Pointing out. Making it better, yeah. Yeah. You know, part of the reason you get into media is because you're interested in engaging with it and 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 journalists face a lot of challenge, though, when it comes to access right now.

44:24Kara Swisher: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 they're direct, direct to customer, essentially. Do you think that is just, that's going to 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 for people to count when they're competing against influencers and these partisan outlets?

44:56Kara Swisher:Because it's a lot easier for them to do that, essentially. Yeah, I mean, I, you know, I wish I had a good answer. I'm not optimistic about it. Meaning? Meaning? 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. Who have you recently gone for that you haven't been able to get? Marjorie Chela Greene in our case. Oh, interesting. I think she doesn't want – because I've said explicitly – I'm going to ask her about the other things. Like I agree with her on a couple of things, but let's ask about trans again.

45:28Kara Swisher:Let's ask about this. And I'm sure the PR people have heard 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 seemed 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. Right. Yeah. No, I mean, I, you know, 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.

46:00And I mean, I've stopped trying as much as as much as I used to, just because it's just so hard to get Republican politicians.

46:07Kara Swisher:Who would you love to get, for example? Who have you not been able to get? Well, Kissinger died. He was number one on my list. You could still do that interview. 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. And so, yeah, there have been – I'm trying to think though who else. I was able to interview Imran Khan, the former prime minister of Pakistan. So that was interesting. He was on my list, people I really wanted to talk to. I don't know. Sean Connery is dead.

46:47My list is quickly getting smaller.

46:50Kara Swisher:Right. Is there anybody that you – your number one person? People always ask me that. I think Modi would be number one. Really? Why? Why Modi? I just, you know, I'm very interested in India. Travel there a lot and I've written about it some. And so he's always interested me. Gosh, mine is Dolly Parton and Taylor Swift together. Okay. Well, you know. Together. Only talking about business. Nothing else. 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. Yeah, that's interesting. I don't know anything about either one of them, I'm sorry to say.

47:22Kara 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 News editor-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 and denied politics played a role, saying she wanted to improve the peace. 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?

47:55Kara Swisher: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. Yeah. I mean I'm fortunate to not have had those pressures either. I had – when I worked at the New Republic, we had an owner who was crazy and bigoted and – Which one?

48:38Marty 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 do what he did in his first term, which is to sort of berate people, but to make regulatory approvals conditional on kissing the ring or whatever else. And I think that that's definitely very scary and, yeah, depressing. I wish I had something more interesting to say about it.

49:24I mean, it's bleak and quite worrisome.

49:29Kara Swisher:If that was presented to you, if you were Sharon Alphonse, for example, what would you do? She wrote a really terrific memo, obviously. Yeah. I mean, 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 the way to go about it is to sort of go public. So in that controversy, because it's the most recent, which one of the people would you want to interview?

50:05Oh, I mean Alfonso probably less than Barry Weiss or David Ellison. But just because I feel like Alfonso'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.

50:27Kara Swisher:See, I would pick Larry Ellison because he's the smart one. Yeah, I was about to say Larry actually. That would have been a good answer. He does the dying is goatee thing, which I find interesting. Yeah, he's a character. I've interviewed him many times, but he's the brains of the operation as far as I can tell. And do you perceive that he has actual deep interest in Paramount acquiring Warner Brothers or do you feel like – I don't. You don't. 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. because it's such a nothing business for him, for someone like him.

51:00Kara Swisher: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? 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. Yes, absolutely. 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, like, he never does dumb things, really. So you're like, why are you doing this dumb thing? So that's who I would interview. It's a good answer, yeah. I want to end by looking at some of the big stories coming in the new year.

51:33Kara Swisher: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 have been accused of violating it. Negotiations around the second phase have stalled. and Trump and Netanyahu are reportedly at odds over what happens next, although they affirm 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?

52:04Kara Swisher:And who would you think is important to talk to for this? 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, a variety of reasons having to do with his corruption trial and political legacy and so on. In terms of that relationship, you know, I thought that what happened at the White House was indicative of it in the sense that, you know, Trump is shown a willingness to push Netanyahu and the Israelis in short term ways, especially earlier in the in 2025. About coming to some sort of ceasefire in Gaza, even though, as you say, it hasn't exactly held.

52:46It's held in some ways, but certainly not. No, there's people are still dying. You know, 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 he 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.

53:21And 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, you know, 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.

53:45Kara 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? 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 was left a lot to be desired in my opinion.

54:24And 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 Whitcoff'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.

54:51Kara Swisher:Yeah. Although I think Whitcoff would be interesting. Wyckoff would be interesting. Wyckoff would be interesting. Here's why. Is he dumb? He seems dumb. So I'd like to know. I'd like to talk to him to find 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. I find this with all conversations. The reason I want to talk to people is to find out if they're dumb. They're dumb. So far, you're smart. So next year is also an election year within the Democratic Party.

55:22Kara Swisher:There are primaries pitting more establishment candidates against progressives. I'm thinking of Senate primaries in Maine, Michigan, Minnesota. There's a lot of issues Democrats have not resolved that divided them in the wake of the 2024 election. Is there areas you're interested in probing with the Democrats? 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 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.

56:11I 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.

56:30Kara Swisher:Is there anyone you're very intrigued by at this moment? I just have to talk to this person. 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 people I consider 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 interesting as possible. Gavin Newsom, Josh Shapiro, Ocasio-Cortez, whoever these people. I think all of them are pretty interesting actually. Have you interviewed Gavin Newsom? No. You'd be good with Gavin Newsom.

57:07Kara Swisher:I'd read the hell out of that. 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 one of the most brutal pieces I've ever read. It is. He's a complex person. Yeah. 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.

57:47Kara Swisher:There's also the AI race in China, Trump's expansion of presidential authority, political violence, escalating tensions with Venezuela, a grueling civil war in 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? I mean I would say that Ukraine and Gaza are two things and – but beyond that, I think – yeah, we touched on this earlier about the question of what's going to happen. There's the next president going to – he's going to be making regulatory decisions based on how much people come and kiss up to him.

58:25Just where the country is headed is – seems like in some ways the big question and that's a question of where the Republican Party is 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 normal normalcy in whatever that meant pre-Trump? And I don't know the answer, but there are 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.

59:14And how much is that sort of a permanent thing or not? So I think those two questions I think definitely interest 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 the intellectual questions I have about where we're headed. What next is what you're essentially saying. Yeah.

59:33Kara Swisher:What next? So that sort of last question, you're doing the exit interview for Trump. He picks you. What would be your first or your last question for him you get to pick? Well, 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 I interviewed Trump and I don't know what I would do. And 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.

1:00:10And just to sort 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. Right. 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.

1:00:47Kara 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? Yeah, it's a definitely definitely a question. It would freak out. It would unsettle them right away. Actually, I'm going to ask one last question. Tell me something personal about yourself that people don't know. Uh, okay. Um, I'm a big, uh, Houston Rockets fan and, uh, yeah, sorry about that one, but no, I'm a big Houston Rockets fan and, uh, very, uh, you know, very anxious fan. Don't handle my emotions well about it. So yeah. Okay. Well, we'll, we'll start with that next time.

1:01:25Kara Swisher: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. Yeah, that was so much fun.

1:01:41Kara Swisher:Today's show was produced by Christian Castro-Russell, Michelle Alloy, Megan Burney, and Kaylin Lynch. Nishat Kirwa is Vox Media's executive producer of podcasts. Special thanks to Sheena Ozaki, Bradley Sylvester, and Madeline LaPlante-Duby. Steve Bone engineered this episode. And our theme music is by Trachademics. 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.

1:02:18Kara Swisher:We'll be back on Thursday with more.