Peter Thiel Photo: Jose Image/Getty Images

On Friday, Gawker Media filed for Chapter 11 bankruptcy. The move follows a devastating $140 million judgment against the company in a breach-of-privacy lawsuit, brought by the former wrestler Terry Bollea (a.k.a. Hulk Hogan) and financed by PayPal founder and Silicon Valley billionaire Peter Thiel. Thiel has nursed a grudge against the company since 2007, when Gawker site Valleywag revealed what, apparently, most of the Valley already knew: that “Peter Thiel is totally gay.”

The judgment, the revelations of Thiel’s involvement, and the subsequent bankruptcy have literalized, in the high dramatics of a pro-wrestling plotline, the complete upheaval of the media business at the hands of the tech industry — in particular Facebook, in which Thiel was an early investor. The saga is also the culmination of an already-weak fourth estate’s worst fears about a new class of superrich. Gawker prided itself on its combative sensibility and unwillingness to flatter the powerful, though an expansive definition of “powerful” may have alienated some bystanders (including the jurors). The apparent success of an aggrieved billionaire in destroying the media company over a personal slight sets a disturbing precedent — paving the way for a future in which “comic-book villain” billionaires can strike down unwelcome coverage with impunity.

But while it’d be easy, and not incorrect, to cast him in the role of a latter-day Charles Foster Kane — à la Frank VanderSloot, the Republican donor who’s offered to fund any lawsuits against Mother Jones — Peter Thiel is more interesting than your run-of-the-mill rich guy. Some of his eccentricities, like his plan to live forever, are to be expected from a high-powered tech entrepreneur. But he’s known for odd politics as well: He’s a big Republican donor in a Valley dominated by Democrats. Though a self-described libertarian, he’s advocated for monopoly and argued that companies should be structured like monarchies. He’s funded idiosyncratic “political” initiatives, such as the Seasteading Institute’s project to create floating libertarian city-states. Famously, in a 2009 essay for Cato Unbound, he declared that he “no longer believe[s] that capitalism and democracy are compatible.” (Thiel has since said that he was wrong to think America was a democracy, calling it instead a “state dominated by very unelected, technocratic agencies”).

Perhaps most interestingly, Thiel’s raised eyebrows by backing Donald Trump — not the candidate you’d expect to be the choice of a science-obsessed, futurist zillionaire. Recent media coverage of Thiel’s support for Trump has tended to focus, naturally, on Trump’s threat to “open up” libel laws and make it easier to sue the press. But there are also a host of odd connections between Thiel’s post-libertarianism and the new forms of right-wing politics that have accompanied Trump’s rise.

Trump has awoken the mainstream media to the “alt-right” and its cousin neoreaction (a.k.a. NRx or the Dark Enlightenment) — loosely related, web-based “movements” that combine internet culture with far-right politics. The alt-right is associated with Trump, 4chan, and anti-Semitic Twitter trolling (think Gamergate and Microsoft’s Tay debacle), while neoreaction, which is smaller and centered on a few major blogs, tends toward intellectual defenses of hierarchy, race science (“human biodiversity”), and the virtues of nondemocratic government. Both exist in opposition to the broadly “liberal” values, like anti-racism and democracy, shared by both sides of the mainstream political spectrum.

Neoreaction has a number of different strains, but perhaps the most important is a form of post-libertarian futurism that, realizing that libertarians aren’t likely to win any elections, argues against democracy in favor of authoritarian forms of government. In this guise, it’s a heretical offshoot of Valley nerd culture, and has particular associations with Thiel. Mencius Moldbug (real name Curtis Yarvin), the “founder” of neoreaction, is a Bay Area programmer whose start-up, Urbit, is backed by Thiel; and reactionary blogger Michael Anissimov was formerly media director at the Thiel-funded Machine Intelligence Research Unit (MIRI). Even Nick Land, the major NRx figure after Moldbug (whom I’ve written about before), has no personal connections to the Valley but shares many of its peculiar cultural interests: Before his neoreactionary conversion, he spent much of the 1990s as a rogue academic writing philosophy-fiction about the Singularity, killer-AI, and time travel. So when it came out that Thiel was attacking a media company and supporting a candidate already perceived as a neo-fascist, it looked a little like some Pynchon-esque conspiracy coming to fruition.

What’s more interesting, however, than Peter Thiel being the shadowy puppetmaster behind a neoreactionary conspiracy — he’s not, and one doesn’t exist — is why he doesn’t need to be. It may seem a little puzzling why a tech entrepreneur, whose own interests include “disruption” and high-modernist sci-fi dreams of space travel and life extension, might get in bed with Trump’s brand of strongman bullying and populist white resentment. But we’re living through a number of crises in our liberal-democratic political system that have no obvious way out, and that are pushing all sorts of different people to react and realign in similar ways. It shouldn’t be a surprise if some are beginning to converge on pretty weird positions.

The first problem — and perhaps the biggest and most obvious — is the economy. Both Trump’s and Sanders’s insurgent campaigns have been premised on anger at stagnant incomes and the decline of mass-employment manufacturing. The big drivers of these are structural forces like trade, technology, and the entry of places like China into the global labor market. None of these can easily be fixed by the state, which means that anger and perceptions of elite failure are only likely to grow. Inequality is persistent, long-term unemployment is still high, and more pessimistic forecasters are suggesting a future in which the labor market is split between a small, highly productive elite and a large underclass rendered unemployable by changes in technology. It’s a view popular among the tech elite, who generally support things like universal basic income (UBI) — free money, essentially — which will allow people to survive, and keep buying widgets, even after the robots take their jobs. Yet the neoreactionaries offer a dark twist on what is usually a story of sunny Valley optimism: Why should the elite consent to be ruled by the poor in such a society, especially if the poor don’t have the leverage that comes when the rich need their labor?

Another major inflection point — to understate the matter somewhat — is race. Racial tensions have been especially high in recent years, from the racially tinged birther movement to the Trayvon Martin shooting and Black Lives Matter. Commentators have pointed out that the alt-right is a form of “white identity politics,” and named Trump as an example of nascent white nationalism. But it’s not exactly clear what white identity even is, and it’s a question worth considering. Germanic and Celtic mythology? Homebrew and vinyl? What about libertarianism, or American nationalism?

If it sounds strange to say that libertarianism is “white,” well, it’s still true. Libertarianism is, empirically, really goddamn white, and some have suggested that that may not be a coincidence: That is, libertarianism makes assumptions about what’s normal for everyone on the basis of the white experience. Normally, that’s a point made by the left as a criticism, but the whiteness of libertarianism is increasingly accepted by post-libertarian reactionaries like Moldbug as a badge of honor. It could also indicate a wider trend in the future, if a combination of demographic changes and political projects to “make whiteness visible” lead more white people to think of cultural values like individual rights as tied to whiteness, rather than as universal principles. Certainly Trump’s brand of nationalism seems to rest on doing something similar with the idea of “America,” abandoning any pretense to a creedal idea of national identity in favor of one based on race. These trends could well produce, among whites, more conscious anti-racists and conscious racists at the same time.

Finally, there’s the question of democracy itself — and the signs of growing disillusion in its ability to confront the problems of the modern world. Andrew Sullivan recently speculated that Trump’s rise reflected the inevitable self-destruction of democracies, setting off a round of fighting about whether we have too much or too little democracy. Affluent urbanites who generally get their way are more socially progressive than the country at large, and popular policies currently include a ban on Muslim immigration. If polarization continues to increase, people may consider that keeping the other side out of power is more important than respecting democratic norms and procedures.

After the Gawker verdict, The New Yorker’s Nicholas Lemann noted that courts have historically treated the press in accordance with public opinion: The less people like or trust the press, the less it’s offered legal protection. In that sense, Gawker’s immediate fate — bankruptcy at the hands of an unsympathetic jury — may be a predictable outcome in a country that has lost faith in its media. But the basic point is larger: Popular legitimacy is just as important to liberal institutions as formal legal protections, and public trust in all major institutions except for the military is declining. If that continues, why wouldn’t we expect those institutions to come under threat? We can see the consequences already among Trump supporters, who are willing to cheer unconstitutional policies because they see laws simply as the arbitrary rules of a hated elite.

It’s here that someone like Peter Thiel is most interesting. He probably wouldn’t describe himself as a neoreactionary, but he wouldn’t have to in order to end up in a similar sort of political place — looking for nondemocratic alternatives as our democratic institutions struggle with mounting problems and declining legitimacy. In a revealing comment to George Packer of The New Yorker, Thiel let slip that he was pessimistic about the current system continuing. The failure of the present Establishment, according to Thiel, may point to Marxism, libertarianism, or something else, but “it’s going to be this increasingly volatile trajectory of figuring out what that’s going to be.” Thiel, obviously, is not a Marxist. He puts his own faith in massive technological breakthroughs, like life extension, that would transform human life without the messiness of social revolution.

Thiel frames these big breakthroughs as “zero to one” innovations — which create something wholly new — rather than “one to n” innovations, which copy and extend something that already exists. Many have connected this “zero to one” frame both to Thiel’s Christianity and his distaste for imitation. James Poulos, however, in a perceptive review of Thiel’s Zero to One, sees in Thiel an echo of Nietzsche’s comment that the “maddest and most interesting ages of history” come when the “actors” — the imitators — rule over the “architects”; status games triumph; and the strength and courage to build for the future is lost. Thiel seems to believe something similar about our current age: He sees his peers as mired in groupthink and imitation, and he longs for the days when technology meant rocket ships and flying cars rather than social media. Scott Alexander, in a contrarian attempt to provide the best possible argument for reaction, suggests that, at a very basic level, it comes down to the idea that in a chaotic and disordered society, sometimes you need a strongman (and “architect”) like Lycurgus to sweep aside the old in order to make room for the new. Thiel often says that the solutions he’s looking for lie outside of politics, in technology. But if we put that together with his claim that “properly understood, any new and better way of doing things is technology,” we might worry about what a political zero to one would look like.