Podcast Summary

Podcast: Free Thinking Through the Fourth Turning with Sasha Stone
Episode: Bari Weiss and the Substack Revolution
Date: September 5, 2025
Host: Sasha Stone
Theme: The impact of Bari Weiss, the Substack movement, and the fallout from media bias—recounting the seismic shift in political and media culture after the publication of Tom Cotton's controversial op-ed in The New York Times, and the subsequent rise of independent voices.

Main Theme Overview

This episode is a deeply personal essay and analysis by Sasha Stone on how Bari Weiss and the "Substack Revolution" reshaped the landscape of journalism, media bias, and public discourse. Stone reflects on the events that unfolded following the infamous Tom Cotton op-ed in the New York Times in June 2020, the reaction from the media, the departure of Bari Weiss, and her astonishing subsequent success as an independent journalist. The episode also explores the host’s parallel journey, the costs of heterodoxy, and the risks and allure of returning to legacy media for figures like Weiss.

Key Discussion Points & Insights

1. The Tom Cotton Op-Ed and Its Fallout

• Stone recalls the moment of paradigm shift: the NYT publishes an op-ed by Senator Tom Cotton calling for the military to restore order during protests/riots (00:00 — 03:20).
• The aftermath included internal backlash at the Times, blaming the op-ed for endangering colleagues and public safety.
• Stone observes the cultural impossibility at the time—labeling unrest as “riots” was itself a “thought crime.”
• "All hell broke loose on Twitter" as internal and external criticism of the Times and Bari Weiss erupted (00:32).

2. Media Bias and the "Negotiated Truth"

• Stone reflects on how the moment made apparent a negotiated version of truth—the “narrative” curated by legacy media (03:20 — 05:48).
• Compares the situation to the film The Insider, spotlighting institutional self-interest outweighing telling the truth.
• Quote:

  "I wasn't getting the truth. I was getting the negotiated truth. The narrative. What they wanted me to know. I began to wonder what else wasn't true."
  — Sasha Stone (07:33)

3. The Impact on Bari Weiss and Legacy Media

• Weiss, then at NYT, became the locus of public anger, accused of endangering black colleagues, and quickly marginalized.
• The infamous official disclaimer added to the op-ed is read aloud (09:46), reflecting the Times’ surrender to internal pressure and the shifting meaning of “editorial standards.”
• Weiss’s fiery resignation letter is quoted:

  "Twitter is not the masthead of The New York Times, but Twitter has become its ultimate editor … Now history itself is one more ephemeral thing, molded to fit the needs of a predetermined narrative."
  — Bari Weiss, resignation letter (13:17)

4. The Substack Revolution & Personal Repercussions

• Bari Weiss becomes a symbol for successful independent journalism, earning a potential $200 million deal with Paramount/Skydance to buy The Free Press and lead CBS News (16:33).
• Stone connects Bari's revolt to their own journey—starting a Substack after being ostracized for heterodox views ("I started a Substack...By then I was already a pariah on my side.") (17:10).
• Quote:

  "On the one hand, I am worried that if I start writing what I've been thinking, it will be met with harsh reprimands. At the same time, there are not enough people on the left willing to speak up … the fear is real."
  — Sasha Stone, first Substack post (18:21)

• For Stone and others, Substack and independent platforms offered freedom from institutional silencing, but at a professional and social cost.

5. The Personal Cost of Heterodoxy

• Stone describes the lived experience of being shunned ("isolating and in some ways terrifying"), called a "MAGA darling" by The Hollywood Reporter, and the irreversible break with prior communities and professional opportunities (19:03).
• Observes that many heterodox writers stop short of openly supporting Trump, but Stone made a full break.

6. Weiss’s Prospects: Independence vs. Legacy Media

• The episode explores the implications if Weiss moves to CBS News—risking her independence and facing institutional resistance (20:51).
• Quote (Megyn Kelly):

  "CBS is among the worst when it comes to being insular...There's no way they're going to respect somebody who did a stint at the Journal and the Times and then went off into independent media as a television editorial boss. And I'm sorry, but they're also not going to respect somebody who's young and a woman, because CBS is not built that way. Again, ask Katie Couric. Ask Katherine Herridge." (19:54)

• Additional Guest Insight:
  • Recounts Pierre Omidyar’s decision to found The Intercept rather than attempt to reform The Washington Post, arguing that even as an owner, changing a legacy institution is nearly impossible (21:14).
• Hosts express skepticism that Weiss could reform CBS, seeing the allure of independence as greater, worrying she may “lose her freedom” (23:12).

7. Final Reflections

• Stone concludes with gratitude for the audience, the importance of independent publications, and the hope that freedom of thought and courage will win out—though recognizing not everyone gets the triumphant ending Weiss may enjoy.
• Quote:

  "Tapping out words on the screen, hoping that those words land in the hearts and minds of readers, hoping that I can be heard. I don't know what I would have done without that. I will never stop saying thank you for saving my life."
  — Sasha Stone (24:38)

Notable Quotes & Memorable Moments

• Stone, on the revelation:
  "I wasn't getting the truth. I was getting the negotiated truth. The narrative. What they wanted me to know." (07:33)

• Weiss, in her resignation letter:
  "Twitter is not the masthead of the New York Times, but Twitter has become its ultimate editor." (13:17)

• Megyn Kelly, cautioning against CBS:
  "CBS is among the worst when it comes to being insular... They hated [Katie Couric's] guts that she didn't rise up within CBS... And I'm sorry, but they're also not going to respect somebody who's young and a woman, because CBS is not built that way." (19:54)

• Stone, on independence and gratitude:
  "Tapping out words on the screen, hoping that those words land in the hearts and minds of readers, hoping that I can be heard." (24:38)

Timestamps for Key Segments

• 00:00 — 03:20: The Tom Cotton op-ed and Twitter/media response
• 03:20 — 06:51: Stone’s personal context during the pandemic, beginning to question the media narrative
• 06:51 — 09:46: The reaction to Cotton’s op-ed, staff outrage, and the NYT’s public disclaimer
• 09:46 — 13:17: Bari Weiss as scapegoat, the chilling effect on dissent, Weiss’s resignation letter
• 13:17 — 16:33: Weiss’s rise to prominence outside legacy media, news of a potential $200M buyout
• 16:33 — 19:03: Stone’s own move to Substack under threat of cancellation
• 19:54 — 21:14: Megyn Kelly cautions about the pitfalls of legacy media for outsiders
• 21:14 — 23:12: Omidyar anecdote; the intransigence of legacy news institutions
• 23:12 — 25:08: Concluding discussion on independence, legacy media, and gratitude to readers

Tone & Language

Throughout, Sasha Stone uses a reflective, candid, and at times polemical tone. She is direct about her personal losses and the chasm created by ideological divergence, while maintaining an undercurrent of hope for free thought, gratitude for her independent audience, and admiration for Bari Weiss's success—even as she highlights its precariousness.

Megyn Kelly’s contribution is conversational and incisive, blending personal experience with industry critique, using plain-spoken and occasionally biting language ("nasty bitches" [23:12]), always reinforcing the hazards of legacy institutions.

In Summary:
This episode is both a chronicle of a media revolution and a meditation on the costs and rewards of intellectual honesty. By tracing the path from Cotton’s op-ed through Bari Weiss’s break and success and Stone's own experience, it squarely confronts the tension between truth, narrative, and the ever-shifting terrain of public discourse. For listeners curious about the evolution of media, the risks of dissent, and the reality of “going independent,” this is a must-hear.