UNLOCK 29.1 Natalie Wynn and Joshua Citarella Cannot Do Everything

Antifascist Dad Podcast, Episode 29.1 Matthew Remski Matthew Remski: Welcome Patreons to Antifascist Dad Podcast episode 28.1. This is called Natalie Wynn and Joshua Citarella Cannot Do Everything. I'm grateful for your support. I hope this project brings some joy and hope and utility to your ears, works and days. And for housekeeping, you can find me on Bluesky and Instagram under my name. And I'm on YouTube and TikTok as antifascistdad and the Patreon for this show, you're probably already on it. It's Antifascist Dad Podcast and you know that you get early access to every second part of the weekly episodes. And my book is now out. It is called Antifascist Dad. The link is in the show notes and if you pick it up, please tell me about it, tell me what you think, maybe review it. And I really appreciate that. So today I'm following up on the audiobook excerpt of episode 28 with an expansion of some remarks that I've made on Instagram about social media punditry and its discontents. And the focus of that has been on an episode of a YouTube podcast called Doomscroll. It's a long form podcast hosted by New York City art and Internet and media critic Joshua Citarella. He's in his late 30s and in this episode he sits with Natalie Wynn, also known as the YouTube video essayist ContraPoints. Now, usually I try to link the two episodes in a given week thematically, but sometimes other priorities intervene, like the news cycle or my own broken attention. You know, and at the risk of stretching a connection here, I do actually think that the following analysis relates to how I go about presenting things in my book. Because what I'll be pointing out about this Doomscroll experience are the problems of accessibility, positionality, scope of practice, and really knowing what your strengths and weaknesses are as a political communicator. And in going through this material, I really realized that what I wanted to do with the book was the opposite of Internet discourse. I wanted it to be grounded, self aware, but not self reflexive. I wanted it to be direct, but I did not want it to be cynical or demoralizing in any way. Now, how successful I've been at that is not for me to decide. But reviewing this piece of media brought those issues into sharper focus. Okay, so first, the basics. What is Doomscroll? This is a long format interview show filmed in a whitewashed New York City or Brooklyn loft space with high ceilings and huge windows and everything's awash in sunlight. Citarella is the host, and he sits across from his guests at a distance that's both close and relaxed. Everything's nicely designed. I think the chairs are probably Eames era originals. There are really clean and fluid edits between the three cameras. The sound engineering is intimate. You can really hear a kind of resonant silence in the space. And I'm opening with the aesthetics here for a reason connected to the idea of habitus that I pinged a few weeks ago. And I'll come back around to that close to the end. But what is the podcast about in general? Well, Citarella's guest list and topics reflect a preoccupation with the intersection of Internet culture, political radicalization and media strategy. So his guests are typically figures working at the edges of liberal or leftist political communication, people thinking about online organizing, subcultural politics, and just the general mechanics of how ideas spread. So guests are people like Matty Healy, Adam Friedland, Ezra Klein, Catherine Liu, Andrew Callahan, Brace Belden, and Dasha Nekrasova. His framing questions tend toward bringing out issues of media ecology rather than really focusing on policy or organizing. So he's interested in how attention works, how platforms shape politics, and why the right wing, especially in the US, has outcompeted the left in all digital spaces. Now, who is Natalie Wynn? She's the creator of ContraPoints, one of the most sophisticated attempts in contemporary media to use high production, just aesthetic pleasure, as a delivery device for left adjacent political philosophy. Now she does these full video film productions that are often three hours long and can take up to a year to create. And she draws on drag performance, psychoanalytic criticism, and continental theory to build these elaborate essays that really seduce followers into a sustained engagement with a lot of ideas that they might otherwise really not have access to, or not know how to access, because they're very bookish, but she makes them sort of explode with visual life. Now, her politics have migrated from explicit socialist empathy — this is, you know, eight, six years ago — towards social democratic liberalism and a kind of pragmatism. And this tracks and also contributes to a broader online left disillusionment. But her significance is less as a political thinker than as a formal innovator. Like, she really showed that YouTube could, you know, host genuinely complex aesthetic and intellectual work. And at least in, you know, very rare cases like hers, it would take off. So where did I intersect with all of this? Like, I can't remember when I started watching ContraPoints, but I do remember the videos dropping like manna from heaven. They were real events. There was a film called Incels that she put out in 2018 that was about the challenges of de-radicalization. There was the film Gender Critical in 2019, which engaged with trans bigotry from her own experience, but also her engagement with trans literature. Opulence was in 2019, and this was like this rococo fever dream about the trouble and joy of aesthetic pleasure. And then she put out Canceling in 2020, which took a self-reflexive turn as she began to really navigate the perils of being an online left-leaning celebrity who's bound to always disappoint someone. And then with Twilight in 2023, she used the series of vampire novels by Stephenie Meyer from 2005 to 2008 that were huge for millennial women. And that was a doorway into discussions of desire, sadomasochism and feminist theory. Now, I'm not a big follower of anyone, so I wasn't really aware of how Wynn's star was rising or falling among her fan base. But I did get wind that she was facing pressure to take a position on the genocide in Gaza and she seemed to be distancing herself from the issue. But in July of 2025, she did comment on it. This is nearly two years after October 7, 2023, and it was in a written statement in which she opposed Israel's military actions while directing criticism at the online left's treatment of Palestine as an omni-cause, crowding out other priorities. Now, this statement triggered a lot of people and provoked a wave of genocide apologist and liberal sellout accusations. And this eventually led her to delete her X account. In August of 2025, she said that she was getting sustained harassment over what she felt were nuanced views. So the harassment sucks. But I do substantially agree with the criticism of her statement, which I'll link to. But basically she opens with this line. Is Israel committing genocide in Gaza? Yes. Do I oppose it? Yes. Do I feel angry about it? Yes. I also feel a lot of other things. And then a lot of other things come in the form of 800 words in which she really kind of focuses on, first, the tactical failures of the online left — like in response to viewing and understanding and wanting to agitate against a genocide. Secondly, the risk of antisemitism arising from pro-Palestinian activism. And you know, that meant invoking the centrality of Jewish feelings, or centering Jewish feelings. Thirdly, she spoke about the futility of anti-Zionism as a political goal, just in terms of the Moneyball numbers of, you know, are you really going to get enough congresspeople to turn away from AIPAC — whatever the reasoning was. You're asking for something that you can't get. And so you should probably cool your heels because the fourth thing is that there's going to be big electoral costs to Democrats. And then I think maybe the thing that I heard a number of other people say who were kind of in this liberal Zionist camp that was very disturbing to me was this question. Well, the way she put it was that the notion that criticizing genocidal policy has saved no Palestinian lives, which is kind of incredible to me. Your protests were useless. In other words. And in the statement, there's no historical analysis, there's no connection to settler colonialism, no mention of the Nakba, 1948, apartheid denied, the 17-year blockade of Gaza before October 7th. No real question of why Western capitalist powers have organized for decades towards the naturalization of this catastrophe. But you know, to be clear, none of this is really unique. It was a pretty standard view for a lot of people. So the question was, why were so many people shocked by it? You know, liberal Zionism is really this posture of, well, yes, genocide is bad, but you know, followed by a cascade of deflection and minimizations that follow. So I'm not shocked or surprised by these views from Wynn because I don't think I ever had the impression that Wynn shared all of my values. I didn't create a halo around her very rich cultural criticism that magically turned her into my full political ally, but a lot of people did. And she wore that halo into Joshua Citarella's whitewashed loft for three hours and 20 minutes. Let me just repeat that — this conversation, this episode was 3 hours and 20 minutes long, and Wynn's squishiness content, like her political views, were right at the center of those 3 hours and 20 minutes. Now out of the box, described as neutrally as I can, this episode is about the challenges facing left political communicators in the current media landscape in the age of fascism. So Wynn and Citarella examine why right-wing content dominates alternative media. They assess left-wing video essays and podcasts as counter-strategies. And they explore the relationship between online political activity and real-world electoral outcomes. They also probe the psychology of Trump support, the gender dynamics of political affiliation, the history of online radicalization, conspiracy theory culture, platform regulation, and the philosophical foundations of Enlightenment liberalism. The conversation ranges across cultural criticism, psychoanalysis, electoral strategy, and personal reflection on a decade of political content creation. Because that's what they've both been up to. That's their field. Now, if that sounds like a lot. Well, it is. And at 3 hours and 20 minutes, it captivated a lot of folks, clocking almost 200,000 views in a week. And most of the commentary, and the most prominent commentary is the 4,000 plus comments now on YouTube, has been about the extent to which Wynn is said to be ambivalent on or retreating from her presumed leftist commitments. And this makes sense because about three quarters of the episode is within the vein of her Gaza commentary — that those on the left who opposed the genocide went too far and neglected other issues. But also they complicated her life personally. But I question the wisdom of spending a lot of time on Wynn's supposed political expertise and on Instagram I said I think we can learn more from a close reading of the limitations of the format itself and the expectations generated by the intersection of online demands and incentives and cultural celebrities. Now, as to their content, it's not like they didn't unpack a number of good points, although at that length you'd hope they would. They explored, for instance, the Brandolini paradox, which is that the energy required to refute bad faith right-wing content is an order of magnitude larger than it is to produce it. They talked about how Joe Rogan's podcast is incredibly successful because he's just a guy and that, you know, it's not primarily coded as political. And so the audience doesn't self-select for political content. It's, you know, selecting also for, you know, well, we're going to talk about MMA fighting, or we're going to talk about health, or we're going to talk about, you know, the weather or whatever they talk about. Now, Wynn and Citarella also pinged the problem that social media no longer allows for closed-door political strategizing. And so that means everyone sees the ugliness of the sausage getting made all the time. Now this is a funny one for them to complain about because throughout they are complaining about leftist online politics and in a sense they're airing their own demoralization in public. They didn't sort of like turn this into a closed-door meeting where they got together all of the top left-leaning influencers and they said, okay, well let's come up with some shared values and policies and best practices. No, they're there to complain at length and they could have, I think, done what they needed to do in about 30 minutes. But the episode is 3 hours and 20 minutes long because some intersection of parasocial desire and the platform demands incentivize them to explore. And I counted all of these 15 different knowledge domains as though they could have competence in them all. So here's the list. They explore political economy, voting behavior, social movements, tech policy, history of political thought, media studies, history of the American left, feminism, communications, the sociology of subcultures and religion, critical theory, conspiracy theories, psychoanalysis, and political and moral psychology. Now they go through these very complex topics, sort of bouncing from one to the other, and they're not just talking out of their asses. About 30% of the claims they discuss are factually based. So, you know, they'll remark that alternative media is 90% conservative. They'll talk about how Jerry Seinfeld dated a 17-year-old. These are all true, these are facts. But what it means is that the rest of the content, 70% of the verbiage, is really in the intuition, opinion, speculation or anecdote category, which would be okay if there was a clear delineation between now I'm presenting data versus now I'm giving an opinion. But the facts become launching pads for these speculative rifts that peak in just unboundaried reflections and sometimes galaxy-brained questions. Like at one point, Joshua asks ContraPoints, should the left abandon the Enlightenment, which is a whole string of, by that point, even in the podcast, undefined terms — or, you know, such broad terms that it's really angels on the head of a pin stuff. And my observation is that no two human beings can possibly provide informed commentary in so many different areas. And so that brings us to the question of what is this 3 hours and 20 minutes, actually. And I believe that it's a showcase of their intellectual performance skills, bathed in a parasocial glow. These people are really good at interesting conversation. They show fluency under pressure. They have confidence, but they hedge it slightly. They have an ability to move across domains quickly, kind of by association, linking things horizontally. And they offer a kind of narrative rhythm and coherence at the expense of analytical precision, I'm afraid to say. And this is why I think conflicts about the politics of the episode is a dead end, because viewers are very easily caught in a kind of eternal netherworld between the ideas and the affects, with different viewers focusing on one or the other and sometimes switching. There doesn't seem to be any ground to the conversation. Now, Wynn's recent political battles do come to the foreground here, but only implicitly, because Citarella doesn't press her on the actual content of her views, but chooses rather to highlight the meta discussion on who was and who wasn't annoyed by this view or that view — by her statement on Israel and Palestine, for example. And so the word Palestine in the 3 hours and 20 minutes isn't mentioned at all. The word Gaza appears once. And this is almost as a tripwire for a lot of focus on whether it was or is or should be okay for Wynn to freely express liberal or soft Zionist views, and whether the backlash to those views from the left defines the left as unrealistic, pragmatic, immature, or hopelessly committed to losing causes. But the discussion of political positioning is — I used the word before — groundless and emotively potent, but vague. So altogether, Wynn and Citarella use the terms the left or leftist over a hundred times in the 3 hours and 20 minutes without clearly defining either term and without naming names, like not even pointing to the negative or toxic figures that we're supposed to pay attention to. According to them about definitions, there's even a kind of notion that the distinction between leftism and liberalism doesn't matter because for all of these sort of Internet weirdos that they're talking about, the main interest is not politics. It's just tribalism. It's just, what team are you on? So there's a lot of hand wringing over the seeming impossibility of creating solidarity on the left. But I think it's disingenuous because their answer to fragmentation is to offer these descriptions of socially irritating, cartoonish groups that are unified by nothing but a lack of sincerity and maturity. So they talk about Discord Communists and Marxist-Leninist tankies, and people who perform impotent radical chic or hide behind theoretical priestliness. But I think one of the most cynical projections in this discourse is the notion that people on the left are in a position where they don't actually want to win because if they did, they would have to sacrifice their victimhood and their contrarian status. So this is the explanation given for why Mamdani is criticized from the left. Not that he's criticized because one should continually hold a leader's feet to the fire. And it's also the explanation they give for the fetish of hopeless causes. Now, during the encampments and in the run-up to Harris's loss, I heard something in the same vein, but a little bit crueler, because the leaders of the uncommitted movement — maybe you remember that these are folks of Middle Eastern descent, mainly in the Midwest, in states like Michigan, who said, we are not going to pledge our support to Harris until — traditional Democrat voters, but we're not going to endorse Harris until we get some kind of statement on a change to policy towards Israel should she win, should she take over the reins from Joe Biden? And of course they were just shut out of everything. But I heard critics say that leaders of the uncommitted movement were selfish for turning the election into a single-issue contest, that they were also sabotaging any chance they would have at power and therefore they were actually harming Palestinians more than Harris was herself. Harris, who was co-signing checks at the time to the IDF. Now, with regard to online leftist acrimony, which is Wynn's focus, I see a lot of BS out there as well. But that is not all there is. Not by a long shot. So I don't buy that Wynn and Citarella's pessimistic impression is any more empirical than my more optimistic one. And that optimistic impression is informed by making it a priority to find and support the people who are doing positive things. I just don't know why I would spend any time on the Internet at all otherwise. But there's also a relevance problem, because without size estimates for these cartoon groups, without documentation of actual political effects, and without distinguishing between the different tendencies and ideologies that they're labeling but not really engaging with, the episode remains unclear about the target. It doesn't answer the questions that I think are really important, which is, according to them, according to their own concerns: is there a significant force that actually disrupts leftist electoral strategy? Or is it a small but visible online minority that's irritating but marginal? Or are Wynn and Citarella just expressing their own personal frustrations at being online celebrities who get into conflicts? I mean, granted, Wynn has earned that frustration. So looking back to a few weeks ago, to my outlining of Jodi Dean's work, I really think it's the conditions of parasocial and communicative capitalism that provoke all of this frustration in the 4,000 plus comments now scrolling out under this episode of Doomscroll. Now, as I said, I'm not alone in disagreeing with Wynn's positions. This is a very common split between the left and those moving towards the center. But part of the virality of this episode is about what those disagreements are and how she responds to them. And those are parts of the ContraPoints brand. And in political terms, I don't think any of that is productive or lucrative except for the platforms. It's just alienation accelerating in many different directions at once. Now, I think that Dean would say that the 4,000 comments are not political participation, but rather pro bono contributions to a circulation system that captures political energy and converts it into platform value. So all the frustration, the disagreement, the brand controversy around Wynn's positions, all of it feeds into a loop. And it's a prickly discourse that feels like politics, with all of the affective intensity, all of the moral stakes, the sense of consequence. And it's that feeling that can displace or demoralize organizing. Consider a few other contradictions that feed this loop. These are two professional commentators on the political communication that they themselves are shaping. They are diagnosing leftist communications failures through a format that exemplifies them. They argue that the left needs more grounding while offering impressions and anecdotes. I think Dean would also argue that they're filling a vacuum. The audience wants an intelligent synthesis of political reality from familiar voices. They want an experience that they're not getting from political parties who host robust internal debate. They're not getting it from labor unions that drive solidarity movements. I just heard that US labor union participation is down to 6% at this point, which is extremely low, maybe a historic low since the 1930s. Local newspapers with specialist reporters, or universities — also not really providing that same kind of familiarity and robust feeling of discourse. So this podcast is filling the vacuum of a dead-on-arrival Democratic Party, and maybe it's even planting a flag in that consultancy field slightly to the left of Ezra Klein's Abundance Posse's flag. So ultimately, I think it would just be great if more of us could be clear on what exactly is capturing our attention here. Because it's not facts, because they don't bring any more facts than anyone else would to any conversation. It's not expertise in any of the 15 subjects, which I think would require research teams and fact checkers. Here's what I think is so beguiling about this format, about this studio, about this conversational kind of product. And I pinged this at the top — there's a loft space filled with sunlight. There are freshly laundered upscale hipster clothes. It's a weekend morning. It's after brunch. This is a daydream about having time — three hours — to talk about something with a good friend who understands you. It's a fantasy of being so well read, so eloquent that you have interesting things to say about anything at all, anything that comes up. This is mainly an aesthetic space. And so it makes sense because that's Citarella's background and it's Wynn's too. Now, with Wynn, there's all this consternation over her political ambivalence, but just how aware are people that that ambivalence and that self-reflection is essential to the ContraPoints technique. That ContraPoints is a persona that's always hedging, always taking some odd or queer angle on things, always shifting between observatory, theoretical and subjective modes. She's proclamatory, she's confessional and everything in between. And in her extraordinary videos she breaks the fourth wall over and over and over again. But if you apply these qualities and those skills to political discourse, you can get some pretty squishy outcomes. The person from history she reminds me of most is Bertolt Brecht, who also fashioned a subversive and self-reflexive queer art. But Brecht always was a committed Marxist and Wynn never was. Never expressed that, never said that. And there's got to be many, many reasons for that, including the post-modernity of the time. So what I take away from all of this is that we have to get our political food from each other. We have to get it offline, or we have to get it from specialists who discuss one thing at a time and give us enough data and grounding to clearly agree or disagree with. And then we can all let Wynn be ContraPoints, a mercurial persona, a captivating gadfly who immerses us in the aesthetics of discourse, not its morality, not its ultimate truth. Thanks for listening everybody. Take care of each other.