Inside the identity crisis in anti-woke media

Yahoo

26-05-2025

The libertarian journalist Michael Moynihan felt the shift on election night 2024, after it had become clear that Donald Trump would win. He was co-hosting a livestream for The Free Press, a new publication that had boomed in response to The New York Times's leftward turn, and was ranting about the dangers Trump would pose to free speech to an impassive group of anti-woke talkers.
'This is one of those many moments when I realized that this wasn't, shall we say, a stable coalition,' he said in an email last week, after leaving a short stint at The Free Press. 'One didn't have to be especially prescient to spot those 'anti-woke' types who would just slowly become MAGA flunkies.'
Moynihan's is a particularly stark example of an identity crisis now tearing through what had been one of the most vibrant slices of American media: the eclectic websites, podcasts, newsletters, and television programs that captured a reaction against left-wing speech-policing, identity politics, and social media-driven protest movements.
That loose group, rooted in part in a letter published in Harper's Magazine in 2020, includes HBO's ,the digital show opinion outlets like Quillette, UnHerd and Persuasion, the Jewish online magazine Tablet, and podcasts like and . Now, they are reckoning with a president who has embraced their positions on many of their favored issues — in particular, the traditional boundaries of sex and gender, the role of affirmative action, and the left-wing slant of American academia — but who is pursuing their goals with the illiberal tactics they'd abhorred.
'There's been a crackup of the wider ecosystem,' said co-host Katie Herzog, along two lines: people who are fanatical about free speech but open to disagreement on issues from Gaza to trans rights and those who would crush their political enemies at the expense of speech; and between liberals who want to reform institutions and radicals who would like to destroy and replace them.
'There's a tendency for some media voices that rose to prominence as 'anti-woke' campaigners to become ever more reactionary. Many of them have also not adjusted to the new reality of the Trump presidency — namely, that 'anti-woke' ideas are no longer heretical and counter-establishment; they dominate the government,' said Freddie Sayers, the publisher of the venerable British conservative magazine The Spectator and of UnHerd. He said the latter outlet has been shifting its focus to follow its audience: UnHerd spends 'more time covering geopolitics, science, religion and less time on culture war issues that are waning in relevancy.'
Sayers — like many others in this loosely organized sphere — tend to take only oblique shots The Free Press, founded in 2021 by former New York Times columnist Bari Weiss. Some said they were worried about getting on the wrong side of a powerful outlet; more said they like and respect Weiss and didn't want to criticize her publicly. But the outlet, by dint of its success — it told Axios it has nearly 155,000 paid subscribers — is often seen as representative of the whole group. It faces a perception, in the words of another contributor, that it's become a platform for 'moderate Trump sycophants,' in part for giving Trump credit for his hostility towards their shared enemies, and for elevating supporters like self-described 'MAGA leftie' Batya Ungar-Sargon. One investigation that exposed two low-profile employees at PBS who had focused on diversity and got them fired rubbed even some of its allies the wrong way.
But it's hardly a MAGA outlet: The Free Press has published a litany of unsigned editorials criticizing Trump on deportations, Russia, the firings of US attorneys, pardons for January 6 rioters, his accepting an airplane as a gift, and other other perceived violations of the rule of law.
Indeed, The Free Press is in some ways sui generis among its generation of media: Weiss is a bankable star; her co-founder and wife Nellie Bowles writes a widely-circulated and politically eclectic weekly newsletter; and The Free Press has attracted A-list columnists like the economist Tyler Cowen.
Still, allies and critics alike obsess about its trajectory, and its relationship to Trump's movement.
'The Free Press is the only one that's serious about politics,' said the conservative activist Christopher Rufo, who drove public attacks from the right on Harvard University and other institutions. He dismissed the rest of the outlets as 'the permanent contrarian, hovering above the discourse casting judgement on whatever coalition is in power.'
He concluded: 'The center-left liberals were not able to 'reform the institutions from within' and are no longer useful as proxies for the right,'
Others see the site's trajectory differently: 'It's perfectly possible to be very anti-woke and very anti-Trump. In fact it's the only coherent liberal and old-school conservative position. But it's hard in our tribal age to find an audience that wants to read — let alone support — both,' said the veteran online journalist Andrew Sullivan. He also cited Maher as someone who has succeeded in 'threading the needle,' and said his own audience is 'used to being pissed off at least half the time.'
'I'd love that to be where The Free Press eventually finds its feet,' Sullivan added. 'It's a work in progress and has amazing talent — so here's hoping,' he said.While some of the anti-woke outlets navigate their mixed feelings about the Trump Administration, others are making a more explicit break with the American right.
One is Quillette, which was launched in 2015 by Claire Lehmann, a former psychology writer based in Australia and a prominent voice in the global debates around gender and identity who has written bluntly that 'Trans activists have no right to pervert the English language.' Quillette made a name for itself by 'criticizing the excesses of progressive activism' in academia and the media, as Lehmann put it.
The publication built up a large following by questioning dominant media narratives around individuals who were driven out of academia, media, or other professional spaces for various misdeeds.
But while the frequent admonishment and skepticism of progressive values helped Lehmann grow the online magazine's subscriber footprint, it also gave some readers on the right a false view of Quillette's values, which Lehmann describes as classical liberalism.
In recent months, the publication has repeatedly criticized Trump, going after his nationalist economic policies, which one columnist described as 'financial illiteracy.' In a piece titled the writer Cathy Young praised the Trump administration's rollback of DEI policies and policies around gender and trans rights. But the publication said those moves paled in comparison to its missteps: its political appointments, defiance of court orders, hardline immigration stance, and trade moves.
'The dizzying rollercoaster ride of Trump's first hundred days has, in many ways, justified and even exceeded the worst fears of those Trump opponents often accused of suffering from 'Trump Derangement Syndrome,' Young wrote.
Quillette has also expressed skepticism of Elon Musk — and, in a particularly pointed break with the attempts to institutionalize the 'anti-woke' movement, ran a piece describing the University of Austin as constrained by its own rigid restrictions on speech and thought.
Lehmann said the magazine had gotten used to criticism from the right during the COVID-19 pandemic by breaking with anti-vaccine conservatives. That move was 'costly for us financially,' Lehmann said, adding that the publication lost a potential investor and a substantial number of subscribers over its pro-vaccine position.
'Going through not being audience-captured does require some pain,' she said. 'Our mission has always been the same, and that is like we criticize anti enlightenment thinking and illiberalism where we see it. It's just that it's more salient in different areas at different points in time.'
She added: 'I would encourage other media entrepreneurs to be a bit bold and disagree with their audience, because although there might be some short term pain, I think it pays off in the long run.'There's little more thrilling in media than having the cultural winds at your back. That was true for The New York Times when it tacked left, caught the wind of the Black Lives Matter movement, and turned the 1619 Project into a brand-defining juggernaut — and then found itself captured ideologically by its own success in crystallizing the progressive moment. It was true of the momentum that Weiss took from her resignation in summer into The Free Press, bringing along tens of thousands of center-left Times readers who disliked the censorious tone and often the substance of the new progressive agenda.
The analogy is imperfect, but I recognize the feeling. I was lucky enough to be a blogger when 'the Web' was the thrilling opposite of the establishment, and to be running BuzzFeed News when social media itself represented a disruptive vertical.
But the wind always shifts. The well-capitalized, well-known, and well-distributed outfits can poach your best talent and absorb your best ideas. The movement with which you're associated can, God forbid, win. Some of the anti-woke voices, like Harvard's Steven Pinker, are now firmly in the anti-Trump camp and decrying the excesses of anti-anti-Semitism in the pages of the Times.
Others will simply be absorbed by the conservative movement. 'The decline of sustained anti-woke media seems to be a product of their own success and Trump's,' said The Spectator's Ben Domenech, who said that he saw most of that group, other than , simply becoming conservative.
'The anti-establishment thinkers became the new establishment. That makes for pretty boring content,' The Atlantic's Helen Lewis told me.
Indeed, Rufo's grouse about reflexive contrarianism is what you'd expect a political activist to say.
In journalism, there's nothing duller, and more soul-crushing, than being an attack dog for the party of power.This splintering has been afoot almost since the reactionary movement's inception, when Blocked & Reported co-host Jesse Singal warned of 'anti-wokeness curdling into reactionary crankery.'
The New York Times in 2020 citing, in part, the dominant role of social media: 'Twitter is not on the masthead of The New York Times. But Twitter has become its ultimate editor. As the ethics and mores of that platform have become those of the paper, the paper itself has increasingly become a kind of performance space.'
The anti-woke right laid the foundation for a new illiberalism, and 'they did so in the most pernicious way possible — by smuggling censorship into American life under the banner of free speech and free thought,' David French wrote in The New York Times.
Part of the new intellectual scaffolding was formed in group chats, as we explored in this space.