Why does Bari Weiss keep winning?
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 “© Vox
