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)

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.

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)

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)

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

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)

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)

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)

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.