Crackpots, Fools, and the Modern Sympathetic Elite

How Reactionary Centrists Enabled Authoritarianism and Helped Sell Liberal Democracy Down the River.

Hannah Arendt, in The Origins of Totalitarianism, observed a startling partnership at the dawn of authoritarian movements: a “temporary alliance between the mob and the elite,” one fueled by the elite’s genuine delight in watching the mob shatter the norms of respectability. Established society’s hypocrisies and pretenses had bred cynical disillusionment. In the the lead up to authoritarians seizing power, vulgarity and cynicism became badges of courage. As Arendt wrote, “vulgarity, with its cynical dismissal of respected standards and accepted theories, carried with it a frank admission of the worst and a disregard for all pretense, easily mistaken for courage and a new style of life”. Elites who felt stifled by liberal pieties eagerly egged on the “mob," the disaffected mass of resentful outsiders, finding thrills in the demolition of decorum.

This alliance was ephemeral and dangerous. Once an authoritarian movement gained momentum, it no longer needed the sympathetic elite except as window-dressing. The moment that power was seized, the movement jettisoned its intellectual fellow travelers and favored the utterly loyal. In one of her most biting insights, Arendt observes that “totalitarianism in power invariably replaces all first-rate talents, regardless of their sympathies, with those crackpots and fools whose lack of intelligence and creativity is still the best guarantee of their loyalty.” In other words, the supposedly "brilliant" rebels who cheered on the mob would eventually be shoved aside by loyal mediocrities. The mob’s triumph meant the eclipse of genuine expertise, and with that, a "carnival of destruction" follows as crackpots are elevated precisely for their pliant stupidity and fanaticism.

Today, there exists a certain reactionary mindset among the elite media class. They claim to reject extremes and posture as voices of reasoned liberalism, even as they fervently platform bigotries and fringe ideas under the banner of brave free inquiry. They share a hatred of the left and a desire to tear down progressive orthodoxies while putting on a veneer of distaste towards conservative politics. They tend to call themselves "heterodox thinkers" yet are anything but. Most importantly, this set is driven by resentment and a deep desire to tear down establishment media that had shunned them and their regressive and reactionary views.

None of this is new. The so-called heterodox thinkers aren't original in their ideas nor are they original in their fake rebellion against the elites they claim to oppose. They have become the “sympathetic elite", aligning with a reactionary mob’s resentment and reveling in the destruction of progressive “respectability.” And just as the sympathetic elite were jettisoned in prior authoritarian movements, the current heterodox crew find themselves at a crossroads in the second Trump administration as they are discarded in favor outlets willing to be blatant propagandists.

Reactionary Centrists as the ‘Sympathetic Elite’

In the mid-2010s, a loose coalition of writers and podcasters coalesced in reaction to what they saw as the intolerant “woke” turn of mainstream liberal institutions. This group, ranging from Substack pundits to new digital magazines, presented itself as politically diverse but united by a mission to challenge left-wing identity politics and so-called “cancel culture.” They resented what they viewed as progressive orthodoxy on race, gender, and sexuality, and styled themselves as heterodox truth-tellers standing up for open debate. They rode the reactionary backlash to Black Lives Matter, MeToo, and trans rights into prominence and lucrative careers. In truth, they were mostly useful idiots or willing accomplices for a deeply reactionary authoritarian movements. Whether they were willing participants or merely too blinded by financial incentives is immaterial for the broader problems they helped create.

These writers are part of an elite disillusioned with the status quo, yearning to smash the “phony” decorum of liberal respectability. Like the intellectuals of 1920s Europe who played at épater le bourgeois (shocking the polite bourgeoisie), the heterodox crew takes palpable glee in violating modern progressive taboos. The thrill of transgression is a driving force. Trolling is seen as a high art form to be aspired to rather than a gutter form of politics that destroys societal decorum. Vulgar cynicism is mistaken for courage. They proudly say the unsayable. They gleefully dismiss the “pieties” of diversity and inclusion as frauds to be torn down.

Bari Weiss is one of the most prominent examples of this trajectory. After resigning from the New York Times in 2020 after decrying its “censorious” woke culture, Weiss set up The Free Press as a platform for all those who felt mainstream media had become an ideological “performance space” beholden to Twitter mobs. Casting herself as a liberal fighting the illiberalism of the progressive establishment, Weiss attracted hundreds of thousands of disaffected readers and quite a few prominent writers. The Free Press trumpets heterodoxy and independence, yet its content skews entirely toward a reactionary narrative. Yet, in the second Trump administration, The Free Press is increasingly becoming a platform for “moderate Trump sycophants” a place where ostensible centrists applaud right-wing populism so long as it targets their shared enemies on the left. Yet they still recoil in horror when the authoritarian Trump administration attacks things they favor, demonstrating a shocking lack of self-awareness of the monster they helped unleash.

Weiss and her circle insist they oppose Trump’s authoritarian streak. Yet they laud Trump when he attacks “their shared enemies” in academia or the media. This is Arendt’s “temporary alliance” incarnate: the anti-woke elite making common cause with a far-right mob, naively believing they can harness its energy without endorsing its worst excesses.

Crucially, these self-anointed centrists derive satisfaction from the illiberal energies they’ve tapped, even as they protest that they themselves remain liberal. Anti-woke contrarianism has been so successful at smashing taboos that it helped pave the way for an openly reactionary governing agenda, leaving the heterodox crew awkwardly cheering a revolution that has become the establishment. The mob has stormed the stage, and the elite onlookers who cheered the chaos must now grapple with their role in empowering it.

Platforming Bigotry as “Open Debate”

A core feature of the heterodox media movement is platforming ideas considered beyond the pale in mainstream discourse, often for good reason. Under the guise of free inquiry and anti-censorship, these outlets have elevated fringe pseudoscience, racial resentment, and anti-trans propaganda, framing them as brave truths that “woke elites” tried to suppress. Today’s reactionary centrist outlets often favor shoddy claims and anecdotal “exposés” that flatter their audience’s prejudices, rather than rigorous analysis that might challenge their biases. Nowhere has this effort been more apparent than on trans issues. This is because trans people make up such a tiny portion of the population with almost no political power. And yet, the dominant narrative of the heterodox crew is how they are brave underdogs exposing the truth against a powerful set of activists. It's almost laughable. The implication is always that polite progressive society is lying to you, and only these brave iconoclasts will tell the “uncomfortable truths.” To the anti-woke mob of readers, this mix of contrarian bombast and cherry-picked data is exhilarating, a chance to laugh at the emperors of diversity and tolerance who, supposedly, have no clothes.

Jesse Singal, a journalist entirely obsessed with the issue of gender affirming care, has made a cottage industry of “just asking questions” about transgender youth, all too often in ways that lend credence to anti-trans panic. Singal got his start pushing anti-trans narratives into the mainstream coming to the defense of Kenneth Zucker, who had been accused of engaging in conversion therapy and hostile abuse in his clinic. Singal framed it in the terms of hostile activists trying to silence a "respected" researcher. In truth, he used the framing of "free inquiry" to begin his career undermining and attacking gender affirming care for trans youth. Singal's broadsides continued in the infamous 2018 Atlantic cover story, where questioned gender-affirming care for trans teens, placing emphasis on the extremely rare cases of regret and detransition while downplaying the far more common positive outcomes. Singal insists he’s no reactionary, yet his work has lent a sheen of respectability to baseless but politically potent notions such as the the debunked idea of “social contagion” spreading trans identity. His writing and his ideas helped spread transphobia among the broader media class that enabled the broader crackdown on trans people by the Trump administration.

The Free Press under Bari Weiss has likewise pursued an anti-“woke” crusade in sensational coverage of trans and gender topics. In early 2023, The Free Press ran a viral story by a supposed whistleblower, Jamie Reed, under the dramatic headline “I Thought I Was Saving Trans Kids. Now I’m Blowing the Whistle.” In it, Reed painted a dire picture of a pediatric gender clinic recklessly harming children. The story caused a firestorm on the right which cited the absurd claims as proof of the evils of “gender ideology” but the claims soon fell apart under scrutiny. Families of patients disputed Reed’s claims, local journalists found key distortions, and an official investigation later concluded there was no evidence of the “morally and medically appalling” misconduct alleged. The Free Press, however, achieved its goal: the anecdote, however flimsy, became propaganda fuel in state legislatures pushing bans on trans healthcare.

Rather than heed the overwhelming medical consensus on trans healthcare, the heterodox playbook elevates a rogue staffer’s lurid tale to “blow up” the narrative. It’s the modern equivalent of preferring a forgery over an inconvenient fact: more gratifying to the mob and thus, in the eyes of these propagandists, more “true” than truth. As Arendt noted, when one is convinced that official narratives are “a forgery anyway,” one might as well turn the whole of reality into a “playground of crackpots”. The Free Press certainly gave the crackpots free rein, and was rewarded with millions of clicks and culture-war cachet for it.

On race and biology, the pattern is just as clear. Quillette, the online magazine founded by Claire Lehmann in 2015, built its brand on courting controversy in the name of intellectual freedom. Lehmann marketed Quillette as “independent” and even “a community of liberal humanists,” yet the site quickly became infamous for showcasing what can only be described as racist pseudoscience. Repeatedly, Quillette published essays arguing that racial disparities in IQ, crime, and wealth are rooted in genetics, effectively laundering long-debunked white supremacist tropes under academic-sounding jargon. Many of its contributors on race were avowed members of the so-called Human Biodiversity (HBD) movement, a thin euphemism for scientific racism founded by a notorious white nationalist blogger. Under the banner of fighting “cancel culture” in science, Quillette gave a platform to HBD evangelists who claim, for example, that certain races are inherently less intelligent or more prone to crime. Mainstream scientists have roundly rejected these claims as junk science, but Quillette embraced them as brave contrarian scholarship. The magazine, as one commentator put it in The Nation, essentially “repackages white nationalist ideas in milder, pseudo-intellectual form and sells them to liberals who aren’t reading closely.” The crackpots in this case have PhDs and write in measured tones, but their loyalty is not to truth or liberal values; it’s to a reactionary narrative that treats equality and anti-racism as naive shibboleths to be smashed.

Arendt pinpointed exactly this dynamic: the elites’ perverse “self-hatred of the spirit” leading them to side with the mob’s vulgar attacks on prevailing standards. The reactionary centrist media elite exhibit a similar self-loathing posture toward their own class of educated liberals. They smirk along with vulgar, resentment-driven discoursel, whether it’s mocking the pronoun etiquette of “woke” college kids, or ridiculing diversity initiatives as sinecures for the undeserving, seeing only the cathartic “lack of hypocrisy” in the mob’s anger, and blinding themselves to the actual content of the hatred being spread. To them, openly expressed cruelty and prejudice appear as refreshing honesty. In this way, reactionary centrists glamorize what Arendt called “the attitude that it’s revolutionary to admit cruelty and amorality, because it destroys the duplicity of bourgeois society”. They mistake shamelessness for authenticity, a fatal error that paves the way for the normalization of political monstrosities.

“Crackpots and Fools” in the Spotlight

The alliance between the sympathetic elite and the mob is inherently unstable. The reason is simple: the very cynicism and destructiveness that make the mob and elite useful to each other preclude any good-faith cooperation. In the end, the mob’s benefactors demand absolute loyalty, not nuanced intellectual support. We can already observe this tension within the so-called "anti-woke media ecosystem," as it tips from heterodox contrarianism into outright "reactionary crankery." Many early participants in the “anti-woke” revolt imagined they could carve out a principled middle ground – e.g., pro-free-speech liberals who disliked campus excesses but also reviled Trumpian attempts to censor and silence critics. Increasingly, that middle ground is vanishing. The gravitational pull of the mob’s agenda is strong. Those who won’t go along may find themselves cast as traitors; those who do will lose any independent credibility.

We see this in the internal rifts and identity crises now plaguing heterodox media. With the re-election of Trump and the mainstreaming of anti-“woke” policies, the once “vibrant” scene of anti-woke websites and podcasts has splintered. Some, like Quillette, have tried to reassert their classical liberal principles by criticizing Trumpist illiberalism, at the cost of hemorrhaging some right-wing audience who expected unwavering culture-war loyalty. This underscores how far the reactionary mob’s expectations have shifted: large portions of the audience wanted Quillette to be purely a right-populist organ, and turned on it when it wasn’t. On the other side, outlets like The Free Press have been rewarded for going harder on the anti-progressive purge, but risk losing their centrist allies. For instance, The Free Press ran an “investigation” that effectively hounded two low-level PBS employees out of their jobs for the sin of doing diversity and inclusion work. This was the kind of "cancel culture" coded work that they once denounced. Some supporters blanched at this petty witch-hunt, seeing it as a betrayal of the heterodox commitment to free debate. But the mob was pleased: another woke outpost was demolished.

Arendt’s prophecy about “first-rate talents” being replaced by “loyal crackpots and fools” becomes tangible if we look at who gets elevated in this ecosystem. Serious academics and journalists who dissent in good faith often end up alienated or sidelined, while true ideologues and grifters rise. But the broader reactionary ecosystem shifted to bomb-throwers and culture war influencers. It became less serious writers and academics with questionable views and instead more of the likes of Libs of Tiktok who use their platforms to silence and censor the political opposition with the implicit support of the Trump administration. These are the loyal crackpots Arendt described: individuals whose very mediocrity or extremism ensures they won’t challenge the party line. They owe their spotlight not to being notable in anything other than being propagandists and attack dogs. Their value is their usefulness in propagating a narrative. Their lack of creativity is their asset; they will dutifully churn out the same rage-bating social media garbage ad-nauseam, never risking true originality or nuance that might conflict with the movement.

Censorship Under the Banner of Free Speech

Another rich irony in the reactionary centrist movement is how quickly their “free speech” crusade curdles into its own form of censorship and propaganda. A revolutionary mob may start by claiming to liberate discussion, but it ends by demanding rigid conformity to its own dogma. We can see this dynamic as anti-woke media help lay the groundwork for new, illiberal orthodoxies even as they claim to oppose intolerance. New York Times columnist David French, a never-Trump conservative, wrote about how the “anti-woke right” essentially smuggled censorship into American life under the banner of free speech. The anti-woke pundits who decried Twitter mobs “canceling” speakers have been notably silent or approving as Republican lawmakers ban school library books en masse and pass laws muzzling teachers from mentioning race or LGBTQ topics. The heterodox sphere’s focus on the supposed tyranny of woke college students has provided intellectual cover for far more dangerous assaults on academic freedom coming from the Right.

The alliance of mob and elite, once it solidifies, doesn’t truly protect open debate, it weaponizes debate as a one-sided bludgeon. We see outlets like The Free Press or Quillette rush to defend professors accused of racism or sexism. But when professors are punished or fired in red states for, say, teaching about systemic racism or for being openly transgender, these “free speech” warriors are quiet. The reason is clear: their outrage is selective, calibrated to the resentments of their audience. Free speech is championed only for those on one side of the culture war. This betrays the fundamental cynicism at the heart of the movement. In the pre-authoritarian spirit, principles are only instrumental. Nothing is inherently true or sacred; everything is a tool to be picked up or discarded in the pursuit of power and the humiliation of one’s enemies. By cloaking vendettas as high-minded contrarianism, reactionary centrists have helped create a public discourse where good-faith standards are dismissed as “political correctness,” and raw resentment gets a rebrand as heroic candor.

The Coming Reckoning: Useful Idiots of Reaction

The “anti-woke” media luminaries consider themselves savvy, voting for the Leopards Eating Faces Party yet confident they won’t themselves have their faces eaten. They believe they can dial up the mob’s sentiments when useful and dial them down when not. Their fatal mistake is that one cannot simply harness a mass movement by accident and escape unscathed. The temporary alliance of elite and mob is just that: temporary. When the mob’s true leaders, demagogues and authoritarians, consolidate power, they have no more need for dilettante allies from the establishment. The very qualities that made the sympathetic elites useful become liabilities under a regime that demands unthinking loyalty.

A perfect example of this is Carl Schmitt. Scmitt was a brilliant conservative jurist who supported Hitler, only to be cast aside for a cruder Nazi loyalist once the Nazis were firmly in control. Similarly, the Trump administration isn’t likely to reward the heterodox crew for their nuanced critique of progressive orthodoxy, more likely, it will deem them insufficiently loyal and replace them with more obedient propagandists. Already, we’ve seen hints of this: figures like Steve Bannon and Tucker Carlson, outright demagogues, command far larger right-wing followings than any highbrow "anti-woke" centrist. The mob gravitates to those who fully embrace its ugly conspiratorial zeitgeist, not those who mince words.

In the end, the modern “reactionary centrists” may well prove to be useful idiots of a nascent authoritarianism. They provided the gloss of intellectual respectability to bigoted populism; they harnessed their education and media skills to make the mob’s resentments trendy. For a while, they reaped the rewards, Substack fortunes, podcast fame, the frisson of being renegades. But as the movement they nourished turns fully against liberal democracy, they will either have to bend the knee or be cast out.

The tragedy is that so many clever people deluded themselves into thinking they could outsmart the extremism they enabled. They forgot that in authoritarian movements, loyalty always trumps talent. The crackpots and fools, precisely because they will never question the party line, are the ones who prevail in the long run. The crackpots of today, far-right influencers, sycophantic culture warriors, are already beginning to take the place of today’s reactionary centrist thinkers as they refuse to fully go along with the authoritarian project.

A Warning to the Heterodox Crew

Hannah Arendt’s brilliant dissection of the mob–elite alliance offers a cautionary tale that the reactionary centrists should heed. While history does not repeat itself in a carbon copy manner, the patterns of intellectual complicity, cynicism, and self-delusion repeat so long as human vanity and resentment persist. Today’s heterodox media darlings believe they are courageously standing athwart the excesses of left-wing zealotry. In fact, they have created a mirror-image zealotry, one that thrives on grievance, traffics in half-truths, and delights in tearing down legitimate social ideals such as equality, pluralism, and diversity under the banner of battling “wokeism.” They have become, in effect, the sympathetic enablers of a reactionary mob. These enablers think themselves the puppet-masters when they are actually puppets of larger historical forces.

When the frenzied "carnival of destruction" has run its course, when respectability lies in ruins and the liberal tradition, flawed as it was, has been thoroughly discredited, the mob will not pause to thank its intellectual midwives. It will toss them aside, preferring the purity of true believers. By cheering the orgy of cynicism and vulgarity, reactionary centrists are sawing off the branch on which they sit. They are helping to usher in a world where truth bows to power, and power tolerates no dissent. In such a world, their nuanced Substack essays and high-minded debates will have no place, except perhaps in a footnote to the history of how liberal democracy was lost.

In Origins, Arendt muses that nothing is more disturbing than the sight of the educated, cultured classes gleefully egging on fanatics in a carnival of destruction. That is exactly what we witness in the reactionary centrist class of modern times. The mob and the sympathetic elite are not new; their alliance is a recurring feature of democratic decay. Knowing that, we have no excuse to be complacent. We can and must challenge today’s crackpots and their enablers with the one thing they fear most: the unwavering defense of truth and principle over nihilism and spite. Anything less, and we risk learning too late, that Arendt’s brilliant but grim insights still hold their sting.