Podcast Summary – On the Media: "The Rapid Rise of Bari Weiss"

Podcast: On the Media (WNYC Studios)
Episode Title: The Rapid Rise of Bari Weiss
Date: December 31, 2025
Host: Michael (Micah) Loewinger
Guest: Peter Shamshiri, co-host of "If Books Could Kill"

Episode Overview

This episode explores the meteoric ascent of Bari Weiss within the media industry, tracing her career from a controversial student activist at Columbia University to her status as editor-in-chief of CBS News and architect of the Free Press, a rapidly growing media organization. Host Michael Loewinger and guest Peter Shamshiri dissect Weiss’s trademark editorial moves, her polarizing reputation, and her impact on the media landscape, especially as she consolidates influence among both disaffected liberals and anti-woke conservatives.

Key Discussion Points & Insights

1. Origins: Early Campus Controversy and Contradictions

• Columbia Years
  • Weiss first emerged in 2004 by founding Columbians for Academic Freedom, targeting professors accused of anti-Zionism, especially Joseph Massad ([00:55]-[02:19]).
  • Shamshiri: “Presenting yourself as having lofty principles that are very directly undermined by your actions. That, to my mind, is just straight down the middle Bari Weiss.” ([01:27])

2. The Canonical Bari Weiss Column: Contrarian Liberalism

• Tablet and Wall Street Journal Days
  • Weiss is noted for her 2015 post-Obergefell gay marriage ruling column focusing less on celebration and more on supposed liberal blind spots regarding Islamic terrorism ([02:19]-[03:46]).
  • Quote: “I'm a liberal. But...” – her signature rhetorical move.

3. The New York Times Era: Platforming the ‘Intellectual Dark Web’ and Fractious Departures

• Op-Ed Editing and Contentious Topics

  • Columns like “Meet the Renegades of the Intellectual Dark Web” and “When Progressives Embrace Hate” critiqued perceived left-wing excess and associated the entire Women’s March with fringe individuals ([03:46]-[05:45]).
  • Notable Quote: Weiss wrote, “We just saw what happens to legitimate political parties when they fall prey to movements that are at base anti-American.” ([05:18])
  • Shamshiri: “Barry is very interested in characterizing the left by its fringe elements.” ([05:45])

• Exit from NYT – Making a Moment Out of a Melodrama

  • Weiss’s resignation letter following the Tom Cotton op-ed controversy positioned her as a victim of “wrongthink” and internal bullying ([06:05]-[07:00]).
  • Shamshiri: “I think about her exit from the Times as a performance by Bari Weiss. … She’s announcing herself to the broader conservative media ecosystem as like a free agent.” ([07:00])

4. The Free Press: Reinventing Conservative Media

• Mission and Style

  • The Free Press declares itself non-ideological: “We don't allow ideology to stand in the way of searching for the truth.” ([08:59])
  • Shamshiri: “Anyone who has read as much of the Free Press as I have will naturally recoil at that statement. … It is very much just a conservative publication.” ([09:19])

• Editorial Pattern: Aggressively Critiquing the Left

  • Little criticism of Trump or the right; left-wing missteps exaggerated. Criticism of Trump is often couched in debate formats, e.g., “Is Donald Trump Breaking the Law? Seven experts weigh in.” ([10:28])
  • Shamshiri: “If the headline would be bad for Trump, the story gets packaged as a debate piece.” ([10:33])

• Growth and Funding

  • The Free Press boasts 1.5 million free and paid subscribers, with 150k paid at $10/month ([11:47]). Investors include Marc Andreessen and David Sacks, but it’s burning through cash quickly ([12:16]).
  • Memorable Analogy: “She's got the Liz Holmes. She can whisper to these rich guys and get their money, get them believing in her cause.” ([12:16])

5. DEI and the Culture Wars: Shaping the Conversation

• Alignment with Conservative Thought Leaders
  • Weiss’s opposition to DEI mirrors Free Press supporter Christopher Rufo and financier Andreessen’s views, hoping to attract disaffected liberals ([12:59]-[13:31]).
  • Shamshiri: “One of the big question marks about the future of the Free Press is how appealing is this style in the new Trump era. … Now with Trump in power, a lot of the Free Press’s output is just going to read like it’s consent manufacturing.” ([13:31])

6. The Woke Right Versus the Woke Left: Maintaining the Narrative

• Framing Ideological Conflict

  • On her podcast “Honestly,” Weiss contends that the radical right is an equal-but-opposite reaction to the left’s extremism ([14:15]-[14:56]).
  • Bari Weiss on Town Hall:
    “When the woke left says trans disabled people of color are the most oppressed class in America and therefore deserve the most privileges, the woke right says, no, no, no. White Christian men have actually been treated like they're at the bottom of the totem pole … creating a new form of identity politics, this time in right wing language.” ([14:56])

• Analysis

  • Shamshiri: “It's a framework for continuing to blame the left for what's happening on the right. … They don't have a ton of interest in understanding the right.” ([15:30])
  • Guests perceive this as a means to justify a “truth-teller” stance, even when right-wing excess is underplayed or rationalized ([16:23]).

7. Who Is the Free Press Really For?

• Media Landscape and Market Conditions
  • Some moderate liberals see the Free Press as refreshing in its willingness to “skewer” left-wing culture, but Shamshiri contends this kind of critique is widespread in mainstream legacy media ([17:12]-[17:38]).
  • Shamshiri: “What's remarkable about Bari Weiss is that she was able to take this style of column that everyone was writing and turn it into a media empire.” ([17:38])

Notable Quotes & Timestamps

• Peter Shamshiri:
  “Presenting yourself as having lofty principles that are very directly undermined by your actions. That, to my mind, is just straight down the middle Bari Weiss.” ([01:27])

• On the O.G. Bari Weiss style:
  “This little move is sort of the basis for her whole career: I’m a liberal. But...” — Peter Shamshiri ([02:48])

• On characterizing the left by its extremes:
  “Barry is very interested in characterizing the left by its fringe elements.” — Peter Shamshiri ([05:45])

• On the Free Press mission statement:
  “Anyone who has read as much of the Free Press as I have will naturally recoil at that statement [about non-ideology]. It is very much just a conservative publication.” — Peter Shamshiri ([09:19])

• On funding and influence:
  “She's got the Liz Holmes. She can whisper to these rich guys and get their money, get them believing in her cause.” — Peter Shamshiri ([12:16])

• Bari Weiss (on identity politics):
  “When the woke left says trans disabled people of color are the most oppressed class in America and therefore deserve the most privileges, the woke right says ... White Christian men have actually been treated like they're at the bottom ... creating a new form of identity politics, this time in right wing language.” ([14:56])

• On Free Press’s unique achievement:
  “What's remarkable about Bari Weiss is that she was able to take this style of column that everyone was writing and turn it into a media empire.” — Peter Shamshiri ([17:38])

Timestamps for Key Segments

• [00:55] Columbia years & academic freedom controversy
• [02:19] Defining the “canonical Bari Weiss column”
• [03:46] NYT’s “Renegades of the Intellectual Dark Web” and Women’s March op-eds
• [06:05] NYT resignation and aftermath
• [07:00] Weiss as conservative media free agent; launching her own platform
• [08:59] The Free Press mission & editorial style
• [10:28] “Experts weigh in” debate format; examples
• [11:47] Free Press’s business strategy, funding, and rapid growth
• [12:59] DEI, culture wars, and ideological alignment
• [14:15] Interview excerpts on “the woke right” vs “the woke left”
• [17:12] Who is the Free Press’s audience? Critiques and perspective on mainstream media
• [18:32] Episode wrap-up and guest close

Memorable Moments

• The analogy comparing Bari Weiss’s investor appeal to Elizabeth Holmes ([12:16])
• The direct quoting of Weiss’s rhetorical style (“I’m a liberal. But...”), highlighting her enduring brand ([02:48])
• The breakdown of Free Press editorial tactics—especially the use of “debate” framing to soften criticism of the right ([10:28])

Conclusion:
This episode provides a critical but nuanced roadmap of Bari Weiss’s career and influence, underscoring the contradictions, strategies, and broader media implications of her ascent. Shamshiri and Loewinger unpack how Weiss has capitalized on public appetite for anti-woke critique, transforming a widely practiced editorial style into a media juggernaut with major political and financial backers—raising questions about the future of ideological journalism in the Trump era.