The Trials of Anti-Woke

On Freddie deBoer, and all the rest

I’ve been asked this a few times and, yes, tickets are still available for my book launch on May 6! We are getting a lot of RSVPs but there is still room before we hit capacity. If you want to join me in conversation with the great Adelle Waldman—and want to hear more about Glass Century, which the writer Matthew Specktor has called “vigorous, confident, controlled, and fiercely intelligent in every line”—you must buy a ticket and secure your spot. And, of course, do not forget to preorder Glass Century, which is now available in all formats: print, audio, and e-book.

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In New York Magazine, where I have a column, I recently wrote about the state of the anti-woke intellectual in America. As with anything regarding “woke” these days, this column attracted a bit of attention, and I was gratified to see readers in conversation with it. I’ll summarize my argument briefly: there were many excesses during the social justice or woke era, which lasted from the 2010s until the early 2020s, but we have entered a new period with the second ascendancy of Donald Trump. Anti-woke is now official U.S. government policy. Karoline Leavitt, Trump’s press secretary, will not respond to reporters with pronouns in their email signatures. The Trump administration is attempting to deport legal residents for criticizing Israel. Colleges and universities face the loss of federal funds if they do not comply with Trump’s demands to eradicate all diversity, equity, and inclusion initiatives and suppress pro-Palestine organizing on campuses. These, to me, are blatant attacks on the First Amendment and the culture of free expression. The social justice era stifled speech plenty—I’ve consistently denounced all of it—and now we see new threats emerging from the state itself. Free speech might be the value I hold most dear. As long as it’s threatened, you’ll hear from me.

In this new era, anti-woke has conquered woke. Beyond certain segments of academia and book publishing, it is difficult to find anyone who engages in the same performatively liberal politics that they used to or makes overly exaggerated appeals to identity. “Latinx” is effectively dead. AOC took the pronouns out of her bio. Gavin Newsom is upset about trans athletes in girls’ sports. I hear fewer land acknowledgements, and not a whit from Black Lives Matter or the remnants of the Women’s March. There is a resistance to Trump, but it does not truly resemble the much broader and culturally dominant version that took hold in 2017. This, I think, is for the best, and I have a suspicion liberals may find more success this time around. I believe that any critique of woke and social justice ideology must begin with the bare fact that, in 2025, it is obviously on the defensive or even totally dead. It was losing steam before Trump took office, but his presidency, to delight of those like Christopher Rufo, has been dedicated to stamping it out for good.

My column did not name Freddie deBoer, the prominent Substacker and author of How Elites Ate the Social Justice Movement, a book I read and largely agreed with. To be frank, he was never on my mind. I trained my fire at Bari Weiss and The Free Press, which I find to be in the untenable position of offering soft support for MAGA while not fully joining the movement. Before 2024 or so, The Free Press had a clear niche as a media organization that would report and opine for liberals and centrists disaffected by the dominance of the silliest strains of identity politics. Weiss, in the 2010s and early 2020s, positioned herself as a free speech warrior, renaming her project The Free Press after beginning it as Common Sense, a smaller Substack. The trouble for Weiss is that she’s an arch-Zionist, and free speech rights mean little to her as long as pro-Palestine activists are being repressed. I believe she’s a hypocrite and I question The Free Press’ long-term health in this new Trump era. It will be financially viable, but how relevant can a publication be when it is unable to firmly challenge MAGA or ride the Trump train? Remember, The Free Press is an explicitly ideological publication. These are questions it is forced to consider.

But deBoer, for reasons that still somewhat befuddle me, took great umbrage with my column. He sent me several emails and then proceeded to blast it on his Substack. Before I respond to him, I will say that deBoer is a writer I’ve sided with on perhaps 95 percent of all issues. I’ve defended him to others. At one time, he even celebrated me in his own pages. I believe his critiques of woke culture have been trenchant and I respect his willingness to confront his own audience, which seems to always want him to disavow the Palestinian movement or trans people.

With that all being said, deBoer has irked me, and I’m going to do what I don’t especially enjoy: responding in a personalized fashion, and pumping venom into my language. I don’t start fights, but I do end them. I don’t shrink from a challenge, and there’s a reason why.

What did deBoer write? Beyond, in a Substack Notes post, calling me a “careerist,” sending a very nasty comment to a friend of mine that I won’t bother to reproduce here, and strongly implying that what I write is not what I believe but is intended to inch myself ahead in this punditry rat race, he argued that I’ve “impressed in recent years by getting some anti-woke content into generally woke-friendly publications.” Fair enough. After linking this essay I wrote last year—one I stand by entirely—deBoer added the following:

I imagine your average New York reader would be pretty surprised that the man wrote today’s piece also wrote these words, and only about half a year ago. I get it: Barkan likely feels that none of this contradicts what he said in the new piece. And I’m not sure that I would necessarily disagree with him. The trouble is that many readers are going to throw out this baby with the bathwater of the trolling, ugly, idiot anti-wokism of the Trump 2.0 era. And that’s why accepting frames like woke and anti-woke is a mistake, even if you think you’re doing so only in the provisional attempt to define priorities and get people to care about what really matters. A lot of New York readers will look at that piece and say, you’re right, anti-woke is poison, let’s get right back onboard with the censorship and the hectoring and the language policing and the performative righteousness. And I couldn’t blame them, given the way that the magazine in particular and the industry writ large have responded to the current crisis.

This doesn’t offend me much. I don’t agree with deBoer—the hectoring and the language policing has vanished, and there’s little evidence it’s returning—but I can nearly understand where he is coming from. If any free speech is violated in a pre-2025 fashion, I’ll be sure to speak out, as I always have.

DeBoer continues:

Barkan is just one worker laboring in the structures his industry is creating for himself, with the most obvious and powerful structure being the ongoing collapse of professional journalism and media and subsequent panicky attempts to consolidate pre-existing readership. For that reason, I suspect that the tension in his anti-woke vs anti-anti-woke stuff are more about the vessel than the liquid that fills it. Barkan has carved out a position as a regular freelancer at New York, one of a small and shrinking handful of publications that can pay and provide a national audience, and that magazine has made its strategy absolutely clear in the Trump 2.0 era: to tell its largely college-educated, largely urban, dominantly liberal readership what it wants to hear. To party like it’s 2015, in other words. The magazine’s rapid descent from being a publication that was at least minimally interested in challenging its audience to being one that’s very reliable when it comes to basic partisan orientation. Go look at what they’ve published since the election, and identify the pieces that would be particularly challenging to your average professional-class New York liberal subscriber. Go look.

And he adds this:

But while Barkan might write towards that ideal, New York is publishing him because it’s what they think their readers want to hear, panic-stricken liberals intent on hearing that not only are they right about Trump now, they were always right, including during the very brief and ultimately inconsequential period in which left-leaning people momentarily considered whether they had gotten anything wrong from 2009 to 2022.

I’m amused to find deBoer imagines me as one drone of a supposed New York Magazine hivemind—a magazine that has, of course, published Freddie deBoer multiple times. I write a column twice a week, an arrangement that very much pleases me. The beauty of New York—and the reason I do this column, beyond the rich legacy of a magazine I grew up reading—is that my editors do, in fact, let me write what I’d like. They don’t force me to do anything I don’t want to do. I pitch an idea, and they’ll let me write it. In his Substack, deBoer indicts me for joining a wave of writers who exist to flatter educated left-liberals. He is furious that Andrea Long Chu, a well-known New York critic I don’t have any deep affection for, published a takedown of Pamela Paul, another writer I don’t especially care for. This has nothing to do with me, just like when one New York Times opinion columnist publishes a piece that completely contradicts what another columnist writes. This is how large media organizations work. “For that reason, I suspect that the tension in his anti-woke vs anti-anti-woke stuff are more about the vessel than the liquid that fills it,” deBoer writes, imagining, it seems, I am yet another data point belonging to his much-shared 2021 polemic—one I enjoyed, by the way—on the state of media; deBoer’s argument is that the economic precarity of digital media explains the cattiness and the groupthink that consumes a great deal of journalists. The trouble with that argument, when applied to me, is that I don’t live a precarious life at all. I’m the rare writer who has found financial success, and I don’t apologize for that. I’ve been lucky, but I’m also good. I can pay my rent, take my vacations, and get new Cole Haan shoes when I want them. I don’t complain.

Of course, my recent column does not tell readers to “party like it’s 2015.” I write, quite clearly, that “the performative aspects of woke were exhausting, and they did chill free speech.” I strongly criticize one of the watershed moments of that era, which was the forced resignation of a New York Times editor over the publication of Tom Cotton’s 2020 George Floyd op-ed. This is not enough for deBoer, though. He complains that I am the man who “who hyperfixates on the momentary turns of today’s politics.” He wants me, in sum, to do more of what he does: continually condemn woke excesses and cry out “never forget” about every 2010s campus controversy. I find this all odd, and deBoer’s arguments wearying. Just because I write on Trump in 2025 doesn’t mean I’ve simply forgotten there was a moment when they held women’s only screenings for Wonder Woman. This is a bit like believing that highlighting the policy victories of the Civil Rights movement is equivalent to completely ignoring Jim Crow. DeBoer accuses me of writing columns to flatter a left-leaning New York audience, but I’ve hardly done that. I don’t know many liberals who wanted to read “What Trump is Getting Right About Ukraine.”

Permit me to be more uncharitable than I’d like, because I typically prefer to keep thoughts like these to myself. From 2021 until 2024 or so, I considered Freddie deBoer to be appointment reading. I consumed, hungrily, every Substack piece he published. It’s plausible I’ve read more than one million words that this man has written, between his books, Substacks, and pre-2021 columns. One of the colder points I can make about deBoer today is that he’s no longer appointment reading, and if he stays on this course, he never will be again. This is no judgment on his success—he’s got more than 65,000 subscribers and grosses, I am sure, something like $400,000 annually. The metrics are inarguable. But there’s a reason many of his most popular pieces were published two, three, or four years ago. There’s a reason I now click on these emails, read two paragraphs, and move on. DeBoer is the starting pitcher with the electric fastball, biting slider, and no third pitch. He is the pitcher who is confused when the batter keeps squaring him up on 2-0. I always know what he is going to say. He is talented and bright, but not nimble. There are many Substackers writing today who are, in my view, appointment reading—Naomi Kanakia, Chris Jesu Lee, Mo Diggs, and John Pistelli are just a small selection—and deBoer fell out of those ranks a while ago.

What all of them have in common—and what deBoer lacks—is an ability to digest the culture in innovating, surprising ways. They all may be classified, in an extremely broad way, as holding anti-woke sensibilities, but they’re going to upend your expectations otherwise. DeBoer’s writing, once refreshing at the height of the social justice bubble, has grown claustrophobic. It’s like getting berated inside a phone booth. Yes, Freddie, we actually don’t need the same exact anti-woke takes you wrote three years ago. That’s because the internet exists; I can go on your page and relish them whenever I’d like. I know how to use the search function.

DeBoer has a diverse but concentrated audience, a mix of genuinely aggrieved leftists and conservatives who want him to flog a liberal a day. This is what audience capture does to you; it convinces you that someone writing a column that never mentions you by name or even alludes to you is personally invested in the destruction of your project. I have no doubt Freddie deBoer is earnest about what he writes. He is a true believer, as am I. But I know his subscribers would not be pleased if he wrote a piece along the lines of what I produced: that anti-woke has beaten woke, and old battles have given way to a new reality. DeBoer thinks I’m too caught up in this moment. I think—and I know I’m right about this—that deBoer has grown too rigid and predictable, and he’s in danger of turning into an anti-woke oldies act. He has his no. 1 hits, and he sure as hell is going to play them for you. I’m about done listening to them. I won’t begrudge anyone, though, who wants to indulge in nostalgia. Everyone has to make a living somehow.