Bari Weiss's Strategy: Critiquing Leftism for Conservative Media Access

On the Media · December 31, 2025 · Listen to Original Episode →

Original Title:

TL;DR

Bari Weiss's career strategy involves presenting herself as a liberal critic of the left, enabling moderate liberals to engage with conservative critiques without identifying as conservative.
The Free Press positions itself as an ideology-free publication, yet its content primarily focuses on aggressive criticism of the left and credulousness towards right-wing narratives.
Weiss's exit from The New York Times was a performance to signal her availability as a free agent to the conservative media ecosystem, leveraging the Tom Cotton op-ed controversy.
The Free Press effectively targets moderate liberals irritated by the social justice left and conservatives uncomfortable with Trump, filling a perceived void in the right-leaning media landscape.
Weiss frames the "woke right" as a response to the "woke left," creating a framework that blames the left for right-wing extremism and perpetuates her analytical style.
The Free Press's success in attracting investors like Andreessen and Sachs, despite significant cash burn, highlights the appeal of its anti-woke stance and its ability to generate substantial revenue.

Deep Dive

Bari Weiss has rapidly ascended to a prominent position in media by cultivating a distinct journalistic brand that critiques progressive orthodoxy, positioning herself as an independent truth-seeker. This strategy has enabled her to build a substantial media enterprise, The Free Press, attracting significant investment and readership by appealing to moderate liberals weary of social justice movements and disaffected conservatives. However, the publication's consistent framing of issues, particularly its aggressive criticism of the left and credulousness toward right-wing narratives, raises questions about its commitment to genuine ideological independence.

Weiss’s career trajectory demonstrates a consistent pattern of challenging prevailing liberal viewpoints, a tactic that has proven remarkably successful. Beginning with her undergraduate activism, she has consistently presented herself as a principled critic of what she perceives as the left’s excesses. This approach was amplified during her tenure at The New York Times, where her op-eds often focused on perceived radical elements within progressive movements, such as the Women's March or the "intellectual dark web." Her departure from the Times, framed as a reaction to perceived "woke" bullying and the handling of the Tom Cotton op-ed, was leveraged into a public declaration of her independent stance, signaling her availability to the conservative media ecosystem.

The subsequent launch of The Free Press represents the culmination of this strategy, establishing a media company explicitly built on "honesty, doggedness, and fierce independence." The publication aims to capture a segment of the media landscape by offering a counter-narrative to what it frames as a monolithic liberal culture, resonating with readers seeking criticism of "wokism" and social justice trends. This has translated into rapid growth, attracting substantial funding from Silicon Valley investors like Marc Andreessen and David Sachs, and a significant subscriber base. The Free Press often frames its output as ideology-free, yet its content consistently prioritizes criticism of the left while exhibiting a notable lack of scrutiny towards conservative figures and policies, particularly regarding Donald Trump and Israel. This selective focus, often achieved through framing and omission, allows the publication to present itself as objective while reinforcing a conservative-leaning perspective.

The implications of Weiss's model are significant for the media landscape and public discourse. By positioning herself as a brave truth-teller against a perceived ideological consensus, she taps into a genuine appetite for critique of progressive movements. However, the consistent application of an "anti-woke" lens, even when examining conservative actions, risks becoming a form of consent manufacturing. This approach may prove less effective in an era where Donald Trump is in power, potentially leading to content that appears to legitimize or excuse right-wing actions rather than critically examining them. The Free Press’s success highlights a persistent tension in contemporary media: the appeal of challenging established norms versus the imperative of rigorous, unbiased reporting, particularly when significant financial and ideological interests are at play.

Action Items

Audit 5-10 recent "Free Press" articles: Identify instances of framing criticism of the left as objective truth (ref: "consent manufacturing" analysis).
Analyze 3-5 "Free Press" opinion pieces: Quantify the ratio of criticism directed at the left versus the right (ref: "aggressive criticism of the left" observation).
Create a framework for evaluating media bias: Define 3-5 criteria for distinguishing between objective reporting and ideologically driven content (ref: "ideology free publication" claim vs. reality).
Track 5-10 "Free Press" coverage areas: Measure the volume of reporting on perceived liberal institutional power versus conservative critiques (ref: "liberal institutions still hold the most power" assertion).
Design a content audit process: For 3-5 articles, assess if criticism of Trump is buried in debate pieces or framed as unresolved questions (ref: "is donald trump breaking the law" example).

Key Quotes

"Presenting yourself as having lofty principles that are very directly undermined by your actions that to my mind is just straight down the middle barry weiss"

Peter Shamshiri argues that Weiss's approach, as exemplified by her actions at Columbia, involves projecting high-minded ideals while her actual conduct contradicts them. This pattern, Shamshiri suggests, is a consistent characteristic of Weiss's public persona and professional activities.

"This little move is sort of the basis for her whole career i'm a liberal but it's very purposefully designed as a way to give the reader permission to agree without feeling like they're being a conservative"

Peter Shamshiri explains that Weiss's career is built on a specific rhetorical strategy: identifying as liberal while primarily criticizing liberal viewpoints. Shamshiri contends that this approach is a deliberate tactic to allow readers, particularly those who might lean conservative, to align with her criticisms without feeling ideologically compromised.

"we just saw what happens to legitimate political parties when they fall prey to movements that are at base anti american"

This quote from Bari Weiss frames her criticism of certain progressive movements, specifically the Women's March organizers, by linking their actions to anti-American sentiments. Weiss suggests that when political groups embrace such movements, their legitimacy is compromised.

"I think about her exit from the times as a performance by barry weiss I think she saw an opportunity and took it"

The speaker views Bari Weiss's departure from The New York Times not as a simple resignation, but as a calculated strategic move. They suggest Weiss leveraged the circumstances surrounding James Bennet's firing to position herself as a victim of internal pressures and an advocate for free inquiry.

"The free press is a media company built on the ideals that were once the bedrock of great American journalism honesty doggedness and fierce independence"

This statement from the Free Press's mission statement outlines its foundational principles. The Free Press asserts its commitment to core journalistic values, suggesting an adherence to truth-seeking and independence above all else.

"The primary theme of the free press's output in my view is aggressive criticism of the left and a sort of remarkable credulousness towards"

The speaker critiques the Free Press's editorial focus, arguing that its content predominantly targets the left with harsh criticism. They also observe a notable tendency within the publication to accept information or viewpoints uncritically, particularly when they align with its perceived agenda.

Resources

External Resources

Books

"The Free Press" by Bari Weiss - Mentioned as the publication she launched and leads.

Articles & Papers

"Meet the Renegades of the Intellectual Dark Web" (The New York Times) - Mentioned as a piece by Bari Weiss that focused on conservative thinkers.
"When Progressives Embrace Hate" (The New York Times) - Mentioned as a piece by Bari Weiss that criticized Women's March organizers.
"Is Donald Trump Breaking the Law" (The Free Press) - Mentioned as an example of a debate piece that framed criticism of Donald Trump as a debate.

People

Bari Weiss - Editor in chief of CBS News and founder of The Free Press.
Erica Kirk - Guest on a town hall hosted by Bari Weiss.
Joseph Massad - Professor whose interactions with students were discussed in relation to Bari Weiss's undergraduate activism.
Linda Sarsour - Organizer of the Women's March, criticized in a piece by Bari Weiss.
Assata Shakur - Black radical mentioned in relation to Linda Sarsour's tweets.
Tom Cotton - Senator whose op-ed at The New York Times led to James Bennet's firing.
James Bennet - Former boss of Bari Weiss at The New York Times, fired over the Tom Cotton op-ed.
Mark Andreessen - Investor in The Free Press, outspoken against DEI.
David Sachs - Investor in The Free Press.
Christopher Rufo - Supporter of The Free Press, described as hoping to corral center-left readers into conservatism.
Rob Dreher - American conservative writer interviewed by Bari Weiss for her podcast.
Jonathan Chait - Op-ed writer mentioned as criticizing the excesses of the left.
Thomas Chatterton Williams - Op-ed writer mentioned as criticizing the excesses of the left.
Conor Freidersdorf - Op-ed writer mentioned as criticizing the excesses of the left.
Bret Stephens - Conservative op-ed writer mentioned.
David Brooks - Conservative op-ed writer mentioned.

Organizations & Institutions

CBS News - Network where Bari Weiss became editor in chief.
Paramount Skydance - Owner of CBS News that acquired The Free Press.
Columbia University - University Bari Weiss attended as an undergraduate.
Columbians for Academic Freedom - Campus group Bari Weiss helped start.
The Free Press - Online publication founded by Bari Weiss.
Tablet - Jewish culture magazine where Bari Weiss worked.
The Wall Street Journal - Publication where Bari Weiss worked and wrote a notable column.
The New York Times - Publication where Bari Weiss was an op-ed editor and writer.
The Women's March - Protest movement criticized by Bari Weiss.
Fox News - Mentioned as a potential outlet for a talking head career.
WNYC - Public radio station mentioned for its history and awards.
New York Public Radio - Organization mentioned for its journalism awards.

Podcasts & Audio

On the Media Midweek Podcast - Podcast where the discussion is taking place.
If Books Could Kill - Podcast co-hosted by Peter Shamshiri, who tracked Bari Weiss's rise.
Five Four - Podcast co-hosted by Peter Shamshiri.
Barry Weiss's podcast (The Free Press) - Podcast hosted by Bari Weiss for The Free Press.

Other Resources

The Intellectual Dark Web - Group of thinkers and writers featured in a New York Times piece by Bari Weiss.
Obergefell ruling - Legal decision that legalized gay marriage, discussed in relation to a Bari Weiss column.
LGBT - Group discussed in relation to a Bari Weiss column on terrorism.
Muslim terrorists - Mentioned as perceived enemies in a Bari Weiss column.
Op-ed - Type of article discussed in relation to Tom Cotton and Bari Weiss's exit from The New York Times.
Black Lives Matter protests - Protests that were the subject of Tom Cotton's op-ed.
Substack - Platform used by Bari Weiss to launch her own media venture.
DEI (Diversity, Equity, and Inclusion) - Concept Bari Weiss has spoken out against.
Woke - Term used to describe a perceived liberal ideology and its perceived excesses.
Woke Right - Term used to describe a perceived right-wing ideology that mirrors the woke left.
Identity politics - Concept discussed in relation to both the woke left and the woke right.
Cancel culture - Concept discussed in relation to criticism of the left.
Social justice left - Term used to describe a segment of the left.
Trump administration - Administration discussed in relation to free speech suppression and other issues.
January 6th - Event mentioned in relation to conservative discomfort with Donald Trump.
Pro-Palestinian protester - Category of individuals discussed in relation to deportation and censorship.
Jihadist students - Term used in a Free Press article title.
Liberal institutions - Institutions perceived by some on the right to hold the most power.
American conservatism - Political ideology discussed in relation to rebranding and new spaces.
Legacy media - Term used to describe traditional news outlets.
Peabody Award - Award won by WNYC.
Dupont Columbia Award - Award won by WNYC.