The Rapid Rise of Bari Weiss

Summary

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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"

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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.

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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])

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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])

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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

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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])

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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.

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Transcript

[A]

Hey, you're listening to the on the Media midweek podcast. I'm Michael Olinger. This year, former New York Times opinion editor Bari Weiss became the editor in chief of CBS News, the network's new owner. Paramount Skydance also acquired Weiss's online publication, the Free Press, for an estimated $150 million. And unconventionally, for a news executive, Weiss appeared in front of the camera in December when she hosted a town hall with Erica Kirk.

[B]

I want, I want to thank Erica Kirk so much for joining me tonight, and I also want to thank our audience for participating in this town hall. CBS News is going to have many more conversations like this in the weeks and months ahead, so stay tuned. More town halls, more debates, more talking about the things that matter. I'm Bari Weiss here in New York. Good night.

[A]

Back in September, I spoke with Peter Shamshiri, co host of the podcast in if Books Could Kill, who's been tracking Bari Weiss's rapid rise. The story starts in 2004, when Weiss was still an undergraduate at Columbia University. That year, she helped start a campus group called Columbians for Academic Freedom and got herself ensnared in a controversy involving a group of professors teaching Middle Eastern and Arab studies, most notably Joseph Massad, a vocal anti Zionist.

[C]

There was one incident where a student asked Joseph Massad whether it was true that Israel gave advance notice to Palestinians in potential danger from incoming airstrikes. Mossad apparently lashed out and basically said, if you're going to defend Israel, get out of my class. Unclear whether that happened. There were investigations that led nowhere. It's very Bari Weiss in that the group that she was part of is branded as one promoting academic freedom, but the entire mission appears to be to get academics disciplined for their views, for the way that they acted in class. 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.

[A]

After she graduated from Columbia, she did a stint at Tablet, the Jewish culture magazine. She then landed a gig at the Wall street journal in 2013. It's there that she writes what you and your co host Michael Hobbs call the canonical Barry Weiss column. This is right after the obergefell ruling in 2015 that legalized gay marriage. Weiss is a gay woman, but her take in the column was less celebration and more finger wagging.

[C]

Yeah, she cites a bunch of incidents of terrorism targeting LGBT folks across the globe and basically says, we are so focused on the opponents of gay marriage in America, but our real enemies are Muslim terrorists. She says the barbarians are at our gates. It's a very classically Barry column because there's this very quick, almost tacit acknowledgement that she agrees with liberals on the issue, but then the entire column is dedicated to criticizing them. 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. There is a thread that you'll see running through a lot of her work. Being relatively anti Muslim and very concerned with Islamic terrorism.

[A]

The New York Times brought her in as an op ed editor and writer on culture and politics. Weiss was often criticized for taking maybe upsetting to liberals positions. Like, there was one piece titled Meet the Renegades of the Intellectual Dark Web, which focused on, you know, Joe Rogan and Jordan Peterson, Sam Harris, Eric Weinstein, up and coming, mostly conservative thinkers and writers. And then a piece titled, quote, when Progressives Embrace Hate, when, which focused on objectionable statements made by four organizers of the Women's March. Break that one down for us a little bit.

[C]

It starts off applauding the principles of the Women's March, but then is primarily a criticism directed at several organizers. Primarily, Linda Sarsour, who's anti Zionist, very explicitly has tweeted in support of Assata Shakur, a black radical who allegedly killed a cop back in the 70s. There's another organizer who was pictured once with Louis Farrakhan. I think you had this really mainstream protest movement in the Women's March that was very correctly identifying the threat from the right wing to women's rights in particular. They were vindicated just a few years later with the overturning of Roe v. Wade. Rather than focus on that, Barry nitpicks her little issues with Linda Sarsour's tweets. I mean, it's just silly.

[A]

What the column does is it focuses on Linda Sarsour's tweets as an example of her radical beliefs, stretches those politics onto a large and fairly diverse protest movement, and then compares it to other scary kinds of extremism. She wrote, quote, we just saw what happens to legitimate political parties when they fall prey to movements that are at base in anti American.

[C]

Yeah, Barry is very interested in characterizing the left by its fringe elements. There are not a ton of people on the broad left in, like, the broad big tent of the Democratic Party who support Assata Shakur, right? Or who know who she is, for that matter.

[A]

The online criticism of her columns, some arguments that were allegedly taking place between her and her colleagues behind the scenes. All of that kind of culminated in 20 when she made a loud exit from the New York Times in the aftermath of her boss, James Bennett being fired over the publication of Senator Tom Cotton's now notorious op ed, which urged the government to send federal troops to crack down on Black Lives Matter protests again in the summer of 2020, she wrote a lengthy resignation letter which described, quote, my own forays into wrong think have made me the subject of constant bullying by my colleagues who disagree with my views. They have called me a Nazi and, and a racist. She wrote that letter just mere weeks after she took to Twitter to call some of her co workers, mostly young wokes. What do we know about her exit from the Times and how do you think it kind of set her up for the next phase of her career?

[C]

I think about her exit from the Times as a performance by Barry Weiss. I think she saw an opportunity and took it. And what I mean by that is James Bennett is forced to resign after the Tom Cotton op ed. The reason for that is not just the substance of the op ed, but the fact that Bennett openly states that he did not review the piece before it was sent to publication, which is presumably part of his job. Barry gets to utilize this moment to portray the New York Times as sort of beholden to, as you said, young wokes, not very interested in free inquiry, free speech at this point. I think it's very clear in my mind that she's announcing herself to the broader conservative media ecosystem as like a free agent. What makes her unique is that she didn't just go become like a talking head on Fox News or whatever. She launches her own substack and tries to sort of create her own media empire.

[A]

You've argued that this time, 2020/2021, was this important era, especially when you look at where the conservative movement was.

[C]

It felt like a moment when conservatism needed a rebrand. It seemed like Donald Trump was fading. It felt like the perfect moment to carve out a new space on the right. And that's what the Free Press seemed to be. It sort of captured two audiences at once. One is moderate liberals who were maybe a little bit irritated by the rise of the social justice left in 2020. And two is the sort of adrift conservatives who were not necessarily comfortable with Trump, who thought that he was gauche and impolite and had crossed the line on January 6th. Barry filled that space very effectively and very quickly.

[A]

In the mission statement for the Free Press, here's a quote. 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. It goes on to say, quote, we don't allow ideology to stand in the way of searching for the truth.

[C]

Anyone who has read as much of the Free Press as I have will naturally recoil at that statement. It's outrageous to think that it is an ideology. Free public publication, it is very much just a conservative publication. The primary theme of the Free Press's output, in my view, is aggressive criticism of the left and a sort of remarkable credulousness toward the right. There are a ton of examples of this. You can go to the website's Free Speech section. There's almost nothing dedicated to the Trump administration's suppression of free speech. In an era where protesters are being targeted, where the administration is targeting universities they don't like, where troops are being deployed to blue cities, the Free Press does not really cover that stuff. There are other things. There is zero criticism of Israel at the Free Press. And something I noticed very consistently is that they will often bury their criticism of Trump in debate pieces. They feature a lot of, like, experts weigh in sort of pieces where they will compile the opinions of different experts on something.

[A]

I read one of these. It's titled, is Donald Trump Breaking the Law? Seven experts weigh in.

[C]

That's right. That piece came out when there was discussion of whether Trump was disobeying court orders. They spoke to seven, I think predominantly law professors. None of them said that Donald Trump was not breaking the law. Several of them said, yeah, he definitely is. And several of them kind of dodged the question and said, well, he's being careless. Bottom line, they found no one willing to say, no, he's not violating the law. And yet that gets packaged in this expert's ha it out style piece that makes it look as if there is room for disagreement. If the headline would be bad for Trump, the story gets packaged as a debate piece.

[A]

Can you give another example of that?

[C]

So Mahmoud Khalil, the pro Palestinian protester who was targeted by the administration for deportation. The pieces are fight club, Should Mahmoud Khalil be Deported? And both left and right are wrong about Mahmoud Khalil. There's a piece titled Deporting Pro Jihadist Censorship or Good Governance. If their concern is free inquiry and competing ideas, then surely you would just allow someone to write a piece criticizing the administration.

[A]

Very clearly, the Free Press has been, by any kind of honest summary, it's been wildly successful. It's grown at an incredibly fast Clip it now has 1.5 million free and paid subscribers. As of July, Bari Weiss has also raised $15 million from investors which include Marc Andreessen and David Sacks. What exactly accounts for this massive valuation? On this, on this newsletter?

[C]

She's got the Liz Holmes. She can whisper to these rich guys and get their money, get them believing in her cause. She immediately invested in expansion in like 2021, 2022, hired staff, raised capital from Silicon Valley types. She's expanded into video and documentaries. Their paid subscribership is well over 150,000 at 10 bucks a month. You're talking about an operation that is generating a good amount over a million dollars a month. And yet, like you mentioned again, did a round of fundraising last year and got $15 million, meaning they're burning through cash at a pretty astounding rate.

[A]

She's been quite outspoken in wanting to see DEI destroyed and kind of rooted out from American public institutions. That's something that we've heard Marc Andreessen kind of beat his drum about quite a bit. Same with Christopher Ruffo, who's a big supporter of the Free Press. In an interview with the New York Times, he called the site, quote, a beautiful off ramp for center left readers who he hopes to corral into his form of conservatism. Is the Free Press flipping readers, as he describes it?

[C]

One of I think the big question marks about the future of the Free Press is how appealing is this style in the new Trump era. It's very easy when Joe Biden's in power to pitch yourself as critiquing the left because the left is in power. That feels like good journalism. Part of the appeal to, to a lot of people was there is a monolithic liberal culture in this country and we need to sort of pierce that. But that's not what things feel like now. Now with Trump in power, a lot of the Free Press's output is just going to read like it's consent manufacturing. I don't know that there's a ton of appetite for that.

[A]

What I've observed is a kind of an anti woke lens applied to even critique of the Trump administration or this right wing radicalization. I listened to the most recent episode of Bari Weiss's podcast, Honestly, which he makes for the Free Press. It's an interview with Rod Dreher, an American conservative writer living in Hungary. The interview is about the rising threat of what he and Weiss called the woke, right, this kind of hyper, online, misogynistic, anti Semitic corner of the Internet that is red pilling Men and boys. She basically says that the woke right is a creation or a response to the woke left.

[B]

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 and they deserve the most accommodations, in effect creating a new form of identity politics, this time in right wing language. It's a fascinating and alarming dynamic, sort of the same phenomenon on each side of the political spectrum.

[C]

It's a framework for continuing to blame the left for what's happening on the right. It's how they perpetuate their style of analysis because they don't have a ton of interest in understanding the right. They view everything that the right wing does as like the organic, reflexive response to the left.

[A]

In the interview, Dreher repeatedly talks about how he supports what Donald Trump is doing to universities and the government. In the same breath as calling out this censoriousness from woke culture, he's also cheering on how conservatives should be targeting what he perceives as liberal institutions, which he and Barry seem to agree still hold the most power in the United States. At one point, he kind of cautions against making a false equivalency between the woke right and the woke left because he's concerned about making the woke right seem as powerful as the woke left.

[C]

It's very interesting where they think the danger comes from. I mean, this is an opinion that you see across the right, that the right is like, besieged. And that view tends to justify their reaction. It's something that you'll see, for example, defenders of the Trump administration cite when you ask about the excesses of that administration. Basically, this is what needs to be done to combat the extent to which the American government has been sort of poisoned by liberalism over the course of decades. That viewpoint is very important to their mission because it is how they allow themselves to believe that they are the truth tellers, that they are the objective ones.

[A]

When I was speaking with a friend of mine, a liberal person who subscribes to the free press and enjoys it, the sentiment that I picked up on was that this reader felt like there's not enough of skewering of the left and honest talk about wokeism in the legacy media, and that here was something that the free press was offering and they enjoyed that kind of cultural criticism.

[C]

I've heard that basic argument before too, and I guess I'm just curious about what legacy media those folks are reading because criticism of the left is really common in these spaces. And not just that, but like the exact style of criticism that Bari Weiss offers is very common. If you're looking for op ed writers who are ostensibly liberal but criticize the excesses of the left, especially focusing on cancel culture, you have Jonathan Chait, Thomas Chatterton Williams, Connor Friedersdorf. You have conservatives like Bret Stephens, David Brooks. I don't really understand the argument that we need more of this. I think there's a ton of 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. I think that's what's impressive about her.

[A]

Peter, thanks for coming on the show.

[C]

It's been an absolute pleasure. Thanks.

[A]

Peter Shamshiri is the co host of the podcast if Books could kill and 5 4. Bari Weiss did not respond to our request for an interview. Foreign. Thanks for listening to the OTM Midweek podcast. If you'd like to support the show, consider dropping us a review on your podcast app of choice. Oh and by the way, in the new year we're going to be posting like a lot more to Instagram and TikTok, so follow us if you don't already. Happy New Year everyone. I'm Michael Olinger.

[C]

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