As Andrew Marantz discovers in his new book, chutzpah – sheer, outrageous shamelessness – may be the most powerful and most dangerous form of charisma.

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The New Yorker writer argues that the unfettered internet created a loose coalition of reactionaries – rightwing muckrakers, pro-Trump trolls and outright fascists – whose cynical exploitation of free speech has derailed American discourse.

The subtext of Antisocial: Online Extremists, Techno-Utopians and the Hijacking of the American Conversation is Marantz’s anxiety at embedding with bad people and his fear that no matter how much critical distance he tries to maintain, the very act of immersion implicates him. As if to prove the point, his book, although dark and often disturbing, is also sometimes funny thanks to its wry, observatorial style and the surreality of the material.

Some of his subjects can charm even as they appall – others just appall – and Marantz is particularly good at dissecting how alt-right trolls use irony and meta-humor and plausible deniability to obscure their horrible beliefs even as they promote them. The result is an impressive work of writing and reporting, probing and profound if not always persuasive.

Disclosure: I know Marantz. He and I have significant differences of opinion. Nonetheless, I can report that his book is well-paced and shot through with vivid detail and scene.

In a typical passage, Marantz describes the lobby of the Trump Hotel in Washington after the 2016 election. He sees “tatted-up Proud Boys”, “notorious 4chan shitlords who seemed flummoxed by the mechanics of face-to-face conversation”, “a former Marine wearing a hunting vest” and “a wealthy deaconess from Nigeria wearing a gaudy church hat”.

“Trump had won,” he writes. “The libs had been triggered. Now the Deplorables drank together in the same glassed-in atrium, listening to the same elevator music, trying to figure out what they actually had in common.”

Despite Marantz’s distaste for his politics, his profile of Mike Cernovich – the men’s rights activist turned alt-lite crusader and would-be lifestyle guru – is empathetic enough to recognize how an unhappy upbringing in an Illinois farm town might explain Cernovich’s hatred of the political establishment.

“Look, if the experts decide tomorrow that we’re going to war with Russia, who’s gonna fight that war?” Cernovich asks. “Jonah Goldberg and Ross Douthat? Fuck no. It’ll be guys I know from Kewanee.”

Another chapter, The Mountain, brings the reader deep into the psychology of Samantha, a young, fairly apolitical woman who gets sucked into neo-Nazism before having a crisis of conscience.

Marantz makes the interesting decision to recount the events of Charlottesville in August 2017 – including the killing of Heather Heyer – through the eyes, or words, of the alt-right. The far-right activist Faith Goldy was on the scene, livestreaming, when James Alex Fields attacked. We see Goldy’s distress quickly give way to rationalization and false equivalence.

The word “Trump” appears less than one might expect. But Trump is, of course, everywhere. Antisocial speaks to what has become a pervasive progressive-left anxiety about the influence of misinformation and disinformation on American democracy. You know: Russian hackers, bots, fake news, “low-information” voters, scurrilous Facebook ads. Marantz laments the fall of the journalistic “gatekeepers” who used to arbitrate public discourse.

But that “gatekeeping” also brought us Vietnam and Iraq and an establishment whose reflexive favor for the status quo often meant quietism about civil rights and poverty.

Marantz recognizes that the gatekeepers had their flaws. His stance on the old media is similar to Churchill’s famous remark that democracy is the worst system except for all the others. But he seems less interested in understanding why the old media lost the trust of so many Americans. He is skeptical of “twerp bashing” – the temptation to take cheap swipes at those who run the prestige media – but misses an opportunity to consider such grievances more seriously.

What if our media gatekeepers – overwhelmingly white, coastal, secular, educated at a handful of elite universities and only 7% Republican – suffer from profound myopias and bias? What if the media was discredited in the eyes of many long before Mike Cernovich or Periscope came along?

Facebook Twitter Pinterest White nationalist demonstrators clash with counter demonstrators in Charlottesville, Virginia in August 2017. Photograph: Steve Helber/AP

Despite his distress at how trolls and reactionaries have “hijacked” democracy, Marantz often seems ambivalent about democracy. For years progressives have claimed rightwing propaganda causes Americans to vote against their self-interest. As the sometime Guardian columnist Thomas Frank put it, “What’s the matter with Kansas?” But when progressives talk like this they don’t seem that different from the social conservatives upset at liberal democracy because it has brought outcomes – “drag queen story hour”, sexual permissiveness – that they don’t like.

The real elephant in the room, made more explicit in Marantz’s recent New York Times op-ed, is his skepticism about freedom of speech. It should be balanced, he argues, against other liberal principles.

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Of course, Facebook and Twitter and Periscope are private platforms. No one has a constitutional “right” to tweet any more than someone can demand the New York Times print their racist screed. I’m OK with putting PR pressure on private tech companies to de-platform bigots and bad actors. But things get murky quickly. A Facebook page advocating genocide is obviously hate speech. But is a group against gay marriage, or a page critical of child gender transition? What about a Twitter bot that just repeats the phrase “All Lives Matter”?

It’s the same with “fake news”. Is a cruel, bullying but factually true statement real or fake news? What about false claims made in satire? What about a claim that is factual but lacks context? Should we ban all conspiracy theories, or just those that are actively harmful? And on and on and on.

Marantz has written what may be the definitive book on the nexus of internet culture and the new far right. Whether it is the definitive explanation of the limits of free speech remains to be seen. Generals are always preparing to fight the last war.