Isaac Chotiner on Confrontation, Curiosity, and Being the 'Interview Assassin'
On with Kara Swisher
New York Magazine
4.2 • 3.2K Ratings
🗓️ 5 January 2026
⏱️ 62 minutes
🧾️ Download transcript
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| 0:00.0 | I'm more explicit than you are. |
| 0:01.4 | I'm like, what you're doing here is this, and you look like an idiot. |
| 0:05.0 | And I actually say you look like an idiot. |
| 0:07.1 | And it tends to work, especially with men. |
| 0:10.0 | You can try it here if you want. |
| 0:11.3 | No, that's okay. |
| 0:12.0 | You're not. I don't need to. |
| 0:13.3 | I would if I had to. |
| 0:14.2 | It's on. Hi, everyone from New York Magazine and the Vox Media Podcast Network. This is on with Kara Swisher, and I'm |
| 0:30.5 | Kara Swisher. My guest today is Isaac Chotner. He's a staff writer for the New Yorker and a principal |
| 0:35.9 | contributor to the magazine's Q&A series. |
| 0:38.6 | Chotner is famous for his intense and sometimes relentless ways of questioning his guests. |
| 0:43.3 | Last year, he went viral for contentious conversations with former White House press secretary |
| 0:47.4 | Corrine Jean-Pierre and legal scholar Cass Sunstein. |
| 0:51.8 | Chotner also isn't afraid to call out other journalists when he thinks they're |
| 0:55.0 | reporting lacks substance, something I completely endorse. I like what Isaac is doing, and one of the |
| 1:01.7 | things I'm going to do this year is focus on people whose work I like. And of course, since we do |
| 1:06.5 | interviews all year long, I want to talk to someone who I think is one of the better interviewers |
| 1:10.6 | these days, in fact, one of the better interviewers these days, |
| 1:11.2 | in fact, one of the best. He's doing a lot of things that other people aren't, which is sort of |
| 1:15.3 | celebrating his own idiosyncratic style, and also really drilling down and getting real |
| 1:20.2 | answers out of people, something I try to do and not always successful at doing, and he often, |
... |
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