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Home News Business

Why does Bari Weiss keep winning?

October 6, 2025
in Business, Culture, News, Politics
Why does Bari Weiss keep winning?
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The anti-woke backlash is coming for CBS News — in the person of Bari Weiss.

In a deal that could have seismic ramifications for the mainstream media, Paramount (CBS’s parent company) will reportedly buy the Free Press (Weiss’s online publication) for around $150 million.

It’s an enormous win for Weiss, an outspoken center-right commentator who quit an editing job for the New York Times’ opinion section five years ago, and who has made criticism of the “woke left” a central theme of her work.

And the capstone is that, as part of the deal, Weiss is slated for a high-level editorial role at CBS News — reportedly as editor-in-chief.

As of this writing, it isn’t clear how Weiss (and Paramount CEO David Ellison, who is arranging the deal) intend to go about remaking CBS News. But of late, Paramount seems to be keenly focused on pleasing the Trump administration and the right.

What is quite clear is that in the five years since Weiss broke with the mainstream media via her Times resignation — she publicly criticized what she said was the paper’s adherence to progressive orthodoxy and intolerance of dissenting views — she’s just kept rising to greater levels of influence and wealth, to her many critics’ deep dismay.

Since its founding a little less than three years ago, the Free Press has become one of the top-earning Substack publications — perhaps the top — pulling in over $10 million a year from about 170,000 paying subscribers.

Among the many anti-woke newsletters on that platform, the Free Press rose to the top for a few reasons. Weiss decided to put together a whole publication, with many writers and contributors, rather than relying just on her own byline. She proved a skilled networker and fundraiser, getting initial startup money from, among others, venture capitalists Marc Andreessen and David Sacks — and following it up by raising millions more.

The influential economics blogger Tyler Cowen, in explaining why he became a Free Press columnist this year, cited its “startup” mentality, Weiss’s “charisma,” and added that the publication “has the audience I wish to reach.”

That audience — disillusioned ex-liberal or centrist elites, often in blue states, who have broken with Democrats and the left but who generally aren’t yet full MAGA or traditionally conservative — has shown up, with their views and their wallets, because the Free Press’s ideological slant speaks to their concerns.

Indeed, one way to understand Weiss’s impact is that she is a convener of a new faction on the right, one organized around recent issues and controversies that shook up traditional political loyalties. And if this deal closes, one of this faction’s champions — arguably its leader — will have a chance to reshape CBS News.

So what does the Free Press faction believe?

The five pillars of the Free Press’s worldview

Though The Free Press has had a variety of writers with different views on various matters, its core worldview, I would argue, has five main pillars.

1. Against the “woke” left

Weiss was one of the many who responded to the “Great Awokening” — the leftward shift among progressives on issues of identity, particularly race and gender — with skepticism and, eventually, outright opposition.

During her New York Times tenure, Weiss was drawn to those who argued something had gone awry in progressive discourse on campuses and elsewhere (she wrote a much-discussed story on a so-called “intellectual dark web”). Her work faced much criticism inside and outside the Times, sometimes for factual reasons, but also because she’d hit a nerve by claiming in the age of Trump that progressives were the intolerant ones.

Tensions came to a head in summer 2020, when the opinion section’s top editor, James Bennet, was forced out after staffers went public to claim that an op-ed he had run had put Black staffers in danger. Not long afterward, Weiss quit too, posting her resignation letter denouncing Times culture on her website. “My own forays into Wrongthink have made me the subject of constant bullying by colleagues who disagree with my views,” she wrote.

Weiss went to Substack, a platform on which many “anti-woke” newsletters thrived. Frustration with wokeness and “cancel culture” was a powerful bonding agent: many people felt they’d been socially ostracized or had to self-censor, and they were tired of it. Before long, Weiss — who had called herself a centrist and said she voted for Joe Biden in 2020 — was making common cause with conservative activists like Christopher Rufo. They had common enemies.

2. Against the “experts”

Many critics of the Great Awokening were particularly perturbed by the shift left of major institutions, such as mainstream media outlets, academia, tech companies like Facebook and Twitter. To them, these institutions seemed totally dominated by progressives, constantly bending to their demands — while those who departed from the progressive consensus risked deplatforming, being accused of spreading dangerous or bigoted misinformation, and having their jobs threatened for saying the wrong thing.

So these institutions and “the experts” in general have become a constant punching bag for the Free Press — portrayed as politically biased and constantly wrong. (The Free Press launched as one of the outlets covering the “Twitter Files” that Elon Musk released to try to impugn his company’s previous owners.)

During the pandemic, these issues of wokeness in institutions had become entangled with criticism of the public health establishment. Skeptics of vaccines, critics of lockdowns, and those pushing for speedier school reopenings all felt their views were being censored. So the Free Press became a home for such commentary — indeed, three of its contributors now have top public health posts in the Trump administration.

Without going “full populist,” the Free Press has also tried to expand the tent for who can count as an expert with views worth taking seriously. When they recently convened a roundup of expert reactions to Robert F. Kennedy Jr.’s tenure as health secretary, they included Zeke Emanuel and Emily Oster — but also vaccine skeptic Alex Berenson and Vani the “food babe” Hari.

But recently, there have been signs that Free Press editors think the pendulum is swinging a bit too much. A recent editorial opens with the requisite fulminations against the public health establishment — before professing to be “horrified” that Florida’s surgeon general wants to end all vaccine mandates for children. It turns out that a ceaseless, years-long assault on the “experts” may bring some undesirable consequences.

3. Supportive of Israel — and outraged about antisemitism in progressive spaces

Since Weiss was an undergraduate at Columbia University in the mid-2000s, she’s been involved in the pro-Israel side of campus controversies; she wrote a book called How to Fight Anti-Semitism in 2019.

These issues were always a part of the Free Press mix, but they became utterly central to its coverage after the October 7, 2023, attacks. The publication cheered on Israel’s war abroad, while arguing that a scourge of antisemitism on US college campuses was making Jewish students unsafe.

But as the war has stretched on, horrific conditions in Gaza haven’t budged Weiss’s support for what she’s called “a war between civilization and barbarism” — one between “good and evil.” This August, a Free Press investigation insisted viral photos of starving Gazan children were misleading, because the children suffered from preexisting health conditions.

Weiss’s critics often argue that her pro-Israel politics makes an awkward fit with her condemnation of other identity politics.“Weiss rails against identity politics as part of left extremism even as Jewish identity forms the central tenet of her own political approach,” the academic Judith Butler wrote back in 2019. Regardless of the internal coherence of this worldview, there’s clearly an audience for it — especially after October 7.

4. Against the (anti-Israel) far right

Relatedly, the Free Press is broadly tolerant toward the contemporary right — including, as we’ll get to in a minute, the president and his top officials. But the faction of the right they criticize the most is the conspiratorial populist far right. Think Tucker Carlson, Alex Jones, and Candace Owens.

In February, Weiss worried in a speech that the “far right” — which she clarified was “not the one defined by cable news” — could devour “what remains of the center right.” Another Free Press article from July argued that “a visible faction of the MAGA movement is revising American history, reviving dangerous conspiracies, and erasing the taboo against open bigotry.”

These complaints are sometimes about explicit professed racism, but they very often tend to be about the antisemitism (sometimes alleged, sometimes indisputable) and criticism of Israel that is common on parts of the online right. And the far right has no love for the Free Press either; commentator Darryl Cooper asserted that the Free Press’s true mission was “to make sure moderate liberals and conservatives newly skeptical of the mainstream narrative stay on the reservation with regard to Israel.”

5. Measured toward Trump and his administration

The Free Press isn’t an avowedly right-wing or pro-Trump publication. Its audience is people who find Fox News or other conservative media too hardline, lowbrow, or sycophantic toward the president. But they aren’t an anti-Trump publication either — far from it.

Indeed, the standard Free Press take on Trump is that he should be understood as a politician with the support of about half the country who does some good things and some bad things — and not as an appalling aberrant figure and budding authoritarian who all decent people must despise. (Weiss has said she bristled at the “overzealous, out-of-touch, hysterical reaction” against Trump in his first term, and asserted that the reaction itself proved “extraordinarily authoritarian and totalitarian in its impulses”).

As Trump began his second term and proceeded to do various extreme and authoritarian things, the Free Press has criticized him about various matters (such as Trump planning to accept a plane from Qatar and going too far in his retribution efforts). But they’ve been strategic about how they do so — being careful not to tip over into becoming an “anti-Trump” publication, since that would cost them their influence on the right).

Some commentators who liked Weiss’s anti-wokeness takes have been appalled at this stance toward Trump’s second term. “The almost total avoidance of coverage of the current government threats to freedoms as basic as habeas corpus, due process and free speech on campus is quite something,” Andrew Sullivan wrote, adding: “When there is coverage, it’s nitpicking in order to defend Trump.”

“Yes, PC-SJW-Critical-Woke-Intersectionality is bad, but some perspective, please,” Steven Pinker posted on X. “Blowing up the international order, sucking up to autocrats, wrecking the world economy, sowing doubt about vaccines, spreading medical quackery, strangling lifesaving foreign aid, pardoning violent rioters, preventing data collection, spewing nonstop lies, & extorting the press, law firms, and universities is worse.”

But the Free Press has found a good deal to like about Trump’s second term — most notably, the strike on Iran, after which they editorialized: “Trump Keeps His Promise on Iran. The World Is Safer for It.”

Can Bari Weiss actually reshape CBS News?

Weiss has spent years pillorying the mainstream media for everything they get wrong, and has built her own alternative. But if the deal with Paramount closes, she’ll face a challenge of a different magnitude — trying to put her stamp on a major, long-established mainstream TV news network: the home of 60 Minutes.

One big question is whether she — and Paramount CEO David Ellison — are hoping to change CBS News to be somewhat more responsive to conservatives’ critiques, or whether they want to fully reshape it into a center-right operation.

According to a Semafor report, Weiss has discussed bringing on her old New York Times opinion section boss, James Bennet. Bennet has written at length about how he thought the Times went astray in 2020, but he isn’t exactly a right-wing ideologue: He was the top editor at The Atlantic and was a contender to become the top Times editor as well before his ouster.

I tend to think that you don’t put Weiss in charge of your mainstream media organization if you are seeking only minor changes. Which means we could be looking at a new version of the “Musk Twitter takeover” playbook — basically a wrecking ball, aimed at demolishing the old institution and creating something more ideologically pliable in its place.

The big question is just what Ellison (the son of Oracle co-founder Larry Ellison, who briefly surpassed Elon Musk as the world’s richest person last month) wants — and why, exactly, he wants to shell out so much cash for the Free Press and Weiss. Little is known about David Ellison’s politics, but his father has long been a Trump supporter, and both are staunch supporters of Israel.

There have also been signs that David Ellison is quite solicitous toward the administration. To get the merger that allowed him to become CEO past Trump’s Federal Communications Commission, Paramount settled an absurdly groundless lawsuit by Trump over how 60 Minutes edited a Kamala Harris interview last year.

Then, once Ellison was ensconced, Trump’s administration complained about how a Face the Nation interview of Homeland Security Secretary Kristi Noem was edited — spurring CBS to suddenly announce that they would now air such interviews unedited.

Last month, CBS News also named longtime conservative think tanker Kenneth Weinstein to be its new ombudsman, in charge of reviewing outside complaints about its coverage — fulfilling a commitment they’d made to the FCC to get the merger through.

How any deal placing Weiss atop the network will play out remains to be seen. Blatant ideological interference will surely lead to staff protests, if not an exodus. But that may be exactly what Weiss wants — to dismantle a citadel of the media establishment and create something new in its place.

The post Why does Bari Weiss keep winning? appeared first on Vox.

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