Wokeness and the Millennial Left

Part II of a conversation between Jon Baskin and David Sessions

This is the second part of a dialogue between Jon Baskin and David Session about the millennial left. You can find the first here, and the third here.

Jon Baskin

This is helpful for understanding how the millennial left saw its project, including both the opportunities and the challenges that it was presented with in trying to build its coalition between downwardly mobile white collar workers (and grad students) and the “traditional working class.” I think it’s also a good setup for what I want to ask in this round about the second topic you focus on in your note: how the millennial left dealt with the rise of identitarianism or “wokeness.” You say that “just because you get into a PhD program at Harvard or freelance for a magazine doesn’t mean you don’t come from a rural town or aren’t still part of a community that includes your blue-collar or Trump-voting relatives,” and that it was in part your ability to connect with those relatives on the leftist economic message that made you optimistic that you could overcome the cultural divide between you and form a political coalition. But it’s exactly in a situation like this that I would imagine the raft of cultural attitudes that came to be known as wokeness would exacerbate the challenge of overcoming that cultural divide, regardless of the comity you could find on economic issues.

In your Substack note, you acknowledge that the left’s perceived embrace of wokeness made things harder for leftists because it associated them in people’s minds with “orthodoxy” or “the establishment.” In response you suggest that this was something of a false perception. For one thing, you say wokeness did not originate on the left, but rather that its “loudest champions in the public sphere were institutional liberal media types that were often anti-socialist or at least anti-Bernie, the Hillary and Kamala 1.0 acolytes in the press.” For another you note that the “actual” left had a “critique of neoliberal identity politics, woke capitalism, all those post-left bugbears, from the beginning.” You then add two caveats: 1) that the left did include some people who embraced woke rhetoric, and 2) that there was a strategic embrace of some of it in response to the left being accused of racism and sexism in the Bernie Bro era.

I agree that it’s far too simple to say that wokeness originated on or was ever the exclusive preserve of the left, but I think this way of putting it risks understating things in the other direction. Some of this has to do, I guess, with which ideas count as “woke”—a notoriously slippery question! I don’t know if you see the defund the police movement, or the prison abolition movement, or the push for open borders as woke—probably there are both “woke” and non-woke articulations of these ideas—but I would say that they all draw on left intellectual traditions and often found their most forceful advocates on the intellectual left in those years. And then there was also the fact that concepts like “intersectionality” and “white privilege,” even if they got taken up and vulgarized by institutional liberals, leveraged a vocabulary that came from academics who claimed to be on the left. So I think there was a lot that from the outside could look legitimately muddled about how far the left was implicated in this set of ideas.

In theory, this should have only raised the stakes for leftist intellectuals at that time to actually explain where they stood. This is where I suppose the second caveat comes in, and I can certainly see how the Bernie Bro smears created incentives to downplay objections to woke ideas, or just to avoid talking about them. But this doesn’t fully make sense of what I remember seeing at the time, which was not only that younger leftist intellectuals seemed reluctant to take definitive stands on identitarian ideas but also that, in many cases, they mounted vicious attacks against anyone who did try to start a discussion about them. In other words, the dominant approach from the left intelligentsia at that time seemed to be a fairly insistent anti-anti-wokeness.

It’s true that some left critiques of identity politics did eventually surface along the lines you reference, but I can’t have been the only one to notice how long it took for most leftists to even acknowledge publicly that How to Be an Antiracist did not in fact offer a fruitful way of thinking about racism in America, and that was low-hanging fruit. (Meanwhile, there was about one article per week attacking Thomas Chatterton Williams, whose book on transcending race had basically zero pickup in the wider culture.) Likewise I would have thought the erection of elaborate DEI bureaucracies, especially at universities, would have been met with withering criticism from a left that claimed to be suspicious of technocratic solutions to social problems, and yet, in the leftist magazines I read (with the occasional exception of Jacobin) there was for a long time almost complete silence on the matter, alongside a steady stream of attacks and innuendo directed toward those who did raise questions about them.

So I am curious to hear you expand on what you said in the note about the determining factors in how the millennial left approached this issue, perhaps accounting for the strength of what I’m calling the anti-anti-wokeness approach. Just to be clear, I am not saying that the millennial left should or could have disavowed everything that was ever called “woke.” There were plenty of serious and important discussions going on in those years about racism, misogyny, immigration, history, and so on—and I don’t mean to shovel them all, as some right-wingers do, into the same bucket. But there was also lots of stuff getting a lot of attention that was really dumb! And going back to that scene with you and your Trumpist relatives, I imagine it would have been helpful in forging the solidaristic economic coalition if the left you were representing had been able to credibly distance itself from the most extreme or incoherent ideas that came out of wokeism, as well as the moralizing and judgmental tone in which those ideas were often conveyed.

Before finishing up, though, I want to be clear about what my main stake in all this was. I had no idea, at the time, whether it was smart, stupid, or a total wash, strategically speaking, for leftist intellectuals to stay on side, so to speak, with the adherents of wokeness. What I had much stronger feelings about was my sense that, in the intellectual world, such strategic considerations were keeping us from being able to have a more honest and critical debate about a set of ideas that had suddenly become culturally central, including about what in them was serious vs. what was incoherent and silly. (This was part of the impetus behind “Tired of Winning.”) I suppose it could be considered part of my incorrigible liberalism that I had confidence such a conversation would be valuable regardless of its political impact, but looking back on this period, I still see it as a missed opportunity for intellectuals of all political stripes in our (broadly speaking) social world to have demonstrated how we could help people to better understand and evaluate a series of ideas that, to many of them, were new, confusing, and increasingly pervasive. (Speaking of the people “back home,” I remember going home myself to Chicago in 2021 or 2022 and finding out that my urban professional friends from my progressive high school were turning to Bari Weiss or Jordan Peterson for help understanding the new ideas they were encountering in their workplace or at their kid’s schools, and feeling like this signaled a real failure of the intellectual world that I considered myself a part of.)

So I also wonder what your perspective is on what made discussing those particular ideas so uniquely difficult, especially within left and liberal intellectual spaces in that period. You mentioned in your note that wokeness actually split both the left and liberalism, and that seems exactly right. I’d add that it contributed to the backlash against both the left and liberalism that we are living through the consequences of right now. But it’s still not totally clear to me what allowed those ideas to be so destructive within both ideological groups, and of course between them.

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David Sessions

Rather than quote extensively, I’m going to summarize what I think are the argumentative points in your response and address them in turn:

1. “Wokeness” may have not come entirely from the left, but at the very least was mixed up in left ideas, spaces, or groups, to the point it was not inaccurate to associate wokeness and the left the way people broadly do today.

2. Leftists were hesitant to criticize wokeness even if they disagreed with it; their position can best be described as “anti-anti-wokeness.” This may have cut against their goal of a solidaristic economic project that involved people who were culturally turned off by wokeness and some of the extreme ideas associated with it.

3. The way this manifested in intellectual life was that everyone was so concerned with strategy that substantive debates about some of this stuff were limited or impossible.

The gist of my response will be that all three points are at least half true, or true in a certain sense, but that I’m not sure how things could have been significantly different, or that a different political outcome would have followed from different intellectual behavior.

Point 1. Let me just start by saying what wokeness is, to the extent it’s even possible to define it. For me it was always more of a style than a substance: a type of performative political posturing that embraces an extreme, reductionist type of standpoint epistemology. It is also a style of combat often known as “cancel culture.” I don’t think that style is congenitally related to left politics; it emerged from the red-in-tooth-and-claw battle for attention on digital platforms. But is indelibly associated with online social justice politics, so it would be ridiculous to say it has nothing to do with leftism. This style, learned on the internet, is also prominent in left organizing spaces of all kinds populated by people millennial-age and younger, though mercifully—mostly—not the particular ones I was involved in. All that to say, I can accept calling those behaviors “leftist” even if neo-fascists, Swifties, YouTubers who cover the drama in TikTok mansions, and others have long done versions of the same thing.

Now, I think it is much harder to say whether a policy idea is “woke,” and there it is important to remember that the concept was given its protean, all-purpose political battle sense by the right. In the period we’re discussing, wokeness had not quite gelled into what it is now. And even though people are already memory-holing this today, the progressive ideas and movements that are now associated with “wokeness” were not as obviously unpopular in the 2016-2020 period as they are now. The George Floyd protests in 2020 were a mass movement, and brought the largest domestic deployment of the military in U.S. history. The scale of the militarized state violence against Americans expressing their opinions was shocking to everyone. It was a vertiginous moment to live through, and lots of people went through their own kind of reckoning, even if something like “defund the police” was never broadly popular. That’s why books by people like Robin DiAngelo and Ibram Kendi flew off the shelves; the people buying them were liberals and normie Americans! Only after that did the right really start making “wokeness” a brand: the Clubhouse event where Christopher Rufo was rallying the right to a strategy of generating battle-concepts like “critical race theory” and “wokeness” was in 2021.

Point 2. I bring that up as a reminder that that earlier moment felt very different than things did by the 2024 election. Obviously 1) the woke style of social justice politics existed, and 2) so did fairly radical ideas like defunding the police, and those were reasonably associated with left academia and organizing. But I’m not sure all this formed a clear “woke” package that socialist intellectuals could have successfully spoken out against. The left does, after all, believe racism is a serious matter, and the fact that millions of Americans were paying attention to it was an exciting opportunity, the kind of political moment where you try to expand your imagination to encompass what is happening organically. As for myself, I would agree my instinct was to be “anti-anti-woke,” but that was because anti-wokeness was so clearly a right-wing strategy. Rufo et al were very explicit that they wanted to delegitimize any discussion of racism whatsoever, and connected it to the muzzling of teachers and destruction of unions. And the center-right liberals who would become the “anti-woke” media complex were not much better; people like Andrew Sullivan and Bari Weiss spoke as if even using the term “white supremacy” about the United States was an outrageous smear rather than the most banal of empirical facts. So I think it’s fairly obvious why some of us on the left felt that we were, for better or worse, on the same side as someone like Nikole Hannah-Jones, who I would call “woke” both in the sense that she embraces the racial-pessimist view of American politics and is a performative, censorious, bad-faith participant in online debate.

That said, I don’t think your characterization is quite accurate that the left were all circling the wagons around wokeness back then. Before the 2020 election there was surely a cautious desire to “stay together” in a loose strategic sense, but there was vigorous debate at the intellectual level. There was an extremely passionate and wide-ranging conflict about the 1619 Project. Socialist-adjacent publications like Jacobin, Dissent, and the New Republic were all at times critical of trendy antiracism discourse; I don’t think it’s true that Kendi long went unchallenged. (Among many others, I would point to Matt Karp and Nikhil Pal Singh.) The left very broadly and vociferously pushed back against the liberal attempt to pathologize Americans as congenitally, incurably racist. But we did to some extent have to respond to the conditions on the ground. That’s why I insisted in my original note that we not forget how broadly popular antiracism was, including among voters and in the establishment part of the Democratic Party and their donors (who the right took to calling “woke capital,” which the left also criticized). That was the challenge: antiracism was motivating people to action, and it’s something we also care about, even if there were versions of it that were theoretically weak or seemed strategically less effective.

Point 3. This gets to your final point, which I think is the real core of your concern, and the argument of your 2018 piece, which was a frustration with what you see as the predominance of strategic thinking over substantive debate. I’ll absolutely concede that it was a hothouse intellectual environment that could be hostile to people who weren’t seen as “on the team.” (My response to your piece at the time is a case in point about that “vibe,” even if I am reiterating a gentler version of its substance here.) I’ve tried to argue so far that that “strategy” dimension was both real—realer than I admitted in 2018—and was also not quite as corrosive to debate as you made it out to be. My guess is that you are less concerned that what left intellectuals did had X negative strategic consequences for their project, which cannot really be demonstrated, and more that what they did contravened your vision of what intellectuals are for. So maybe I’ll say more about how my own understanding of what intellectuals are for has shifted since then and turn back to some questions for you about that vision.

In the 2016-2020 period, I explicitly modeled myself on the “party intellectual” in the Communist sense, even though my own sensibilities have always been—like those of many party intellectuals of the past—instinctively liberal and oriented toward intellectual freedom rather than political instrumentalism. The history of the left is rich with people who tried to square that circle, to negotiate the competing roles of political prophecy and political science. Marxist theory had a sociological critique of intellectuals—one that came in vulgar, reductionist versions and more sophisticated versions—as potentially useful but also usually unreliable because of their bourgeois ideology of intellectual freedom (which usually happens to align with what the dominant interests in society want to hear). As I wrote in my “autocritique” of my intellectual practice in that period, I was trying an experiment, to be both as rational and objective as possible, but in the service of a political mission; I wanted ideas to be good and rigorous, yes, but I wanted to ally them with a mission we might call propagandistic.

And that certainly meant the “strategic” emphasis that you disliked back then, and that I am less beholden to now, even if I don’t think we can directly blame any particular failure on it. A party intellectual, in my understanding, was not their own, they were a vessel of the movement and tried to use their intellect to sharpen and steer it. They were an idealist who put their elite tools in the service of the less privileged, which was possible because of their own intermediary position between the elite and the people. I was thinking about socialist-adjacent European intellectuals in my dissertation, and also had in mind China Mieville’s October, which presented Lenin and the Bolsheviks not as top-down dictators, but intellectual-organizers who were dragged along by the demands of the people, and sometimes had to give up their own theory about what was ideal and meet the moment. The Socialist Revolutionary Party was in crucial moments bigger and to the Bolsheviks’ left, and wanted things Lenin’s party thought it wasn’t the right time for. But it became clear that the revolution was happening with or without them, and they had to compromise.

That’s how I saw some of the wokeness stuff, for a while: this is what the people are doing, and it would be pointless to tell them they’re wrong; instead we have to use it the best we can and educate them toward a higher version of it. That didn’t mean no arguments about it or no attempt to steer in a certain direction; I think we had many of those. I don’t think even now that being committed to a project and strategic about it is an illegitimate form of intellectual practice, especially when it is done thoughtfully; virtuous intellects always have to weigh aims that are in tension with each other and do the best they can in each unique case. You can’t just throw up liberal-humanist platitudes about intellectual freedom as if they answer every question, because they don’t—intellectuals are never really “free.” But it did perhaps mean a certain narrowness of vision and a somewhat myopic hostility to people who weren’t focused on that mission in a particular way.

My own shift since then has been mostly a personal one of accepting my vocation as a generalist public intellectual, not an activist or adviser to a movement. I’m aware that that follows a now-clichéd historical script of intellectual burnout with left political engagement. But I’ve tried not to present it as some road-to-Damascus conversion to a righteous liberal humanism. I respect people who do serious work with activist aims, and of course we still just as much need rigorous work on labor, economics, global governance, and all the things we focused on in the socialist moment. But personally I’m just not going to worry if what interests me is directly instrumentalizable by a movement; if I want to read Plato or write about literature, and that is not directly political, then so be it—it is valuable nonetheless. I would never have become a leftist in the first place without a Great Books education. How I would put it now is that my work is not apolitical or anti-political, but tries not to be hyperpolitical. But I can’t really blame anyone for being intensely politically focused during an intensely political, historic moment in American politics—or say that such a thing won’t happen again. Some of this is cyclical: certain ways of seeing things may be right but have diminishing returns as they calcify through repetition, and one needs a breath of fresh air.

Read the next and final part of this conversation here.