The Gist – Finding the Next Terry Gross with Daniel Oppenheimer

Podcast: The Gist
Host: Mike Pesca (Peach Fish Productions)
Guest: Daniel Oppenheimer
Date: December 13, 2025

Episode Overview

In this lively and thought-provoking episode, Mike Pesca sits down with writer and podcaster Daniel Oppenheimer to tackle the looming question: “Who should succeed Terry Gross as host of NPR’s Fresh Air?” The conversation delves into what sets a great interviewer apart, why not every celebrity or even every journalist is suited for the job, and whether the kind of authentic, searching interviews Gross pioneered can or should be replicated. Along the way, Pesca and Oppenheimer name potential successors, critique some notable podcast hosts, and offer sharp insights into the craft of interviewing itself. The episode is rich with behind-the-scenes radio knowledge, podcast industry dynamics, and candid, sometimes funny, self-assessments by Pesca about his own interviewing style and ambitions.

Key Discussion Points and Insights

1. Why Terry Gross Is So Good (08:35–10:00)

• Universal Admiration & Unmatched Skill: Both host and guest agree Gross is the gold standard for interviewers, even calling criticism of her as eccentric as calling The Beatles overrated.
• “Her greatness sometimes gets in the way of the interview…” (09:32, Mike Pesca): Pesca notes that Gross’s reputation can sometimes overshadow her guests.
• Insider Stories: Pesca shares details from his time at NPR, such as being able to listen in on the raw, unedited Fresh Air interviews—offering unique insights into her process.

“She’ll ask many preambulatory questions. ‘Is okay if I ask this?’... She taught me a lot about interviewing, and a lot about when I do the kind of interview I do where things can be cut. It’s a very specific kind of interview.” (10:30, Mike Pesca)

2. What Makes a Great Interviewer? (13:10–14:34)

• Emphasis on letting the guest reveal themselves rather than centering the host.
• Contrast drawn between journalists and celebrities as hosts: Journalists (especially those experienced in print) bring an investigative rigor, whereas many celebrity podcasts offer style over substance.

“Their job is professional interviewer. Not guy who starred in Arrested Development who also knows a bunch of people who can be interviewed.” (12:50, Mike Pesca)

• On Ross Douthat’s Interviewing: Pesca and Oppenheimer discuss Douthat’s standout episode with Curtis Yarvin, praising Douthat for letting Yarvin "have enough rope" to reveal his own flaws (14:06–14:43).

3. The Art of the Interview: Preparation and Authenticity (15:45–19:44)

• The Magic Behind Terry: Gross’s method is characterized by preparing deeply and constructing the interview in real time—many threads are tested and ruthlessly edited.

“You come away with every chunk—even the ones that don’t work—were given the best chance... and could be incorporated into the rest of the interview.” (17:44, Mike Pesca)

• Preparation vs. Performativity: Comparisons are drawn with podcasts like those by Sam Sanders and Sam Fragoso, with Pesca and Oppenheimer critiquing "performative" styles that lack authentic engagement.
• Marc Maron: Praised by Pesca for his preparation (contrary to popular belief), particularly with guests he's interested in.

4. Who Should Succeed Terry Gross? Pesca’s Shortlist (19:46–33:42)

American Hosts

• Colin McEnroe (WNPR Hartford): Pesca calls him the current best daily radio host (19:46).
• Sam Sanders: Noted for his cultural fluency and personal style, though Pesca finds his presentation somewhat “calculated” (20:42).
• Margaret Brennan (Face the Nation): Praised for her pointed, non-performative questioning (22:44).
• Sam Fragoso: A self-referential interviewer with “transferable skills” but maybe too introspective for Fresh Air (23:23).
• David Marchese (NYT Culture): Excellent print interviewer, capable on audio; known for deep preparation, even if some interviews (Vince Vaughn) were controversial (28:46–29:29).
• Elvis Mitchell (The Treatment): Renowned for insightful, mind-blowing questions (30:10–31:05).

  “At one point, Dave Chappelle kind of breaks character...and says, ‘Elvis Mitchell, you just blew my mind.’” (31:05, Mike Pesca)

• Mike Birbiglia: Stand-up comedian and director noted for thoughtful conversations with comedians that go beyond the usual "craft talk" (31:43–32:53).

Non-Americans

• Helen Lewis: British journalist and podcaster, called a “great talker and a great writer,” especially on political language (33:16–33:42).
• John Ronson: British journalist and documentarian with a distinctive, honest approach—“a little off-kilter” but capable of extracting candor from unusual guests (33:43–34:43).

5. The Celebrity Host Problem (12:19–13:10)

• Strong distaste for minimally-prepared, celebrity-hosted podcasts, exemplified by SmartLess:

"They're terrible... Their shtick is they don't prepare, but... it’s not so spontaneously delightful that it gets over that gigantic flaw.” (12:19, Mike Pesca)

6. The Pros and Cons of Pesca as Host (34:55–38:12)

• Strengths: Good listening, real-time engagement, ability to elicit genuinely new responses.
• Weaknesses: May take the interview into niche territory that’s less accessible for the general Fresh Air audience (41:18–41:24).

“If I bring the Fresh Air audience an interview with the director of the Amanda Knox story and we spend 15 minutes on FOIA...I don't know how many people will [enjoy that].” (41:18, Mike Pesca)

• He admits his tastes might be “self-limiting” but believes in differentiating with depth rather than formula.

7. Balancing Audience Needs with Interviewer Curiosity (37:54–42:22)

• The challenge of not boring yourself as an interviewer vs. serving a mass audience who want familiar content.

“I struggle with that in my own interviewing because I'm just so easily bored... but that's not most listeners.” (38:12, Daniel Oppenheimer)

• Recognition that interviewers can serve as audience proxies but must balance novelty with the need to provide some expected context.

8. Memorable Interview Experiences & Self-Critique (42:40–44:30)

• Pesca shares highlights where high-profile or resistant guests opened up (“interviewers’ thrill”).
• Critiques the sometimes limited inquiry on the political side of Fresh Air (“A+” for culture, “B+” for hard news).

“I might give an A minus to B plus to when she gets on a New Yorker writer...I don't think...she doesn’t push back.” (43:51, Mike Pesca)

9. Meeting Terry Gross and Final Reflections (44:30–46:54)

• Pesca shares his embarrassment after asking Gross to have him on Fresh Air (“I felt really embarrassed afterwards.”) (44:31)
• Reflects on career hopes and the reality of being an everyday podcaster.
• Pesca’s final picks for a sudden vacancy: “I'd call Colin [McEnroe]... and if it was Hail Mary...Helen [Lewis] or John [Ronson]” (46:31).

Notable Quotes & Memorable Moments

• On the value of in-depth preparation:
  “She is so good. And I do, by the way, think her current co-host is not nearly as good. I will say generously and maybe leave it at that...” (08:35, Mike Pesca)

• On letting guests speak for themselves:
  “It wasn’t about Ross saying, ‘Here, let me tell you my thoughts.’ It was about Ross letting Yarvin very much tell the audience who he really is. That’s one of the main things you want an interviewer to do.” (14:10, Mike Pesca)

• On listener expectations and interview innovation:
  “On Fresh air, the idea is this is your first listen. Most of our listeners over the air, half of them have never listened to a podcast...They listen to Fresh Air to hear an interview about Amanda Knox, and that is the one interview they’re gonna hear.” (41:24, Mike Pesca)

• On interviewing itself:
  “Listening to all the other interviews they’ve given and knowing what they’re going to say...you’re not looking to poke a hole, but you’re looking to ask the follow up question that none of those hosts did ask...” (36:49, Mike Pesca)

Timestamps for Important Segments

• [08:13] – Kickoff: “Who should be Terry Gross’s successor?”
• [10:30] – Peek behind the scenes of Gross’s interviewing process.
• [12:19] – Critique of celebrity-hosted podcasts.
• [14:10] – Why letting the guest lead matters.
• [15:45] – Lessons from uncut Fresh Air interviews.
• [19:46] – Pesca’s shortlist: American candidates.
• [22:44] – Network TV interviewers: strengths and weaknesses.
• [28:46] – Print journalists as interviewers: The David Marchese example.
• [30:10] – Why Elvis Mitchell stands out.
• [33:16] – Helen Lewis and John Ronson as “wildcard” successors.
• [34:55] – Pesca’s self-assessment.
• [38:12] – Serving the audience vs. innovation.
• [41:18] – The niche vs. mass appeal challenge.
• [44:31] – The awkwardness of meeting Terry Gross.
• [46:31] – Final picks: who should step in “tomorrow.”

Conclusion

This episode offers a candid, nuanced, and often witty examination of what it takes to be a great interviewer—and a fitting successor to Terry Gross. Pesca’s shortlist ranges from old-school American radio hosts to British intellectuals, but throughout, he keeps the focus on authenticity, deep preparation, and a genuine curiosity about the guest over showmanship or celebrity. The episode is essential listening or reading for podcast fans and aspiring interviewers, blending industry wisdom, personal anecdotes, and critical takes on today’s audio culture.