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On with Kara Swisher

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

On with Kara Swisher

New York Magazine

Society & Culture

4.23.2K Ratings

🗓️ 5 January 2026

⏱️ 62 minutes

🧾️ Download transcript

Summary

As the principal contributor to The New Yorker’s “Q&A” interview series, Isaac Chotiner has earned a reputation as “the interview assassin.” His persistent questioning has made for some awkward — and revealing — conversations with high-profile guests over the years, but Chotiner also rejects the caricature of the “gotcha journalist” that’s often applied to him. Kara and Isaac talk about his interviewing style, how he prepares for difficult conversations, and his recent viral Q&As with the legal scholar Cass Sunstein and former White House Press Secretary Karine Jean-Pierre. They also talk about some of the stories that are likely to dominate headlines in 2026. Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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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