The Teacher and the Troll King: James Baldwin and Milo Yiannopoulos in the Age of Social Media

Copyright: konstantin32 / 123RF Stock Photo

We in the left need to regain Baldwin as a model. For the moment, we have ceded the territory. There are no more Baldwins. Only Yiannopouli.

This is going to be difficult. Hear me out.

Lately, we’ve had a peculiar confluence of two names that have re-arisen in the popular imagination: Milo Yiannopoulos and James Baldwin. Yiannopoulos, the disgraced now-former Breitbart Editor, for his outlandish and self-aggrandizing remarks, and Baldwin, for his popular rediscovery in the Oscar-nominated documentary currently in Cinemas entitled I Am Not Your Negro.

Below is a video of a famous encounter between the late James Baldwin, known then as a famous author and essayist, and the late William F. Buckley, founder of the conservative National Review and one of the last in a long line of conservative intellectuals that appear to have stayed quiet recently, or perhaps abandoned the Republican Party to its curious fate altogether, in the age of you-know-who.

Watch this.

To have read Baldwin is to have been captivated by the unique, seething intelligence that often comes from people who have been forced to live outside multiple boundaries and spheres of protection, as he did as a gay black man in mid-20th century America. One guesses he must have been compelled to confront and digest the outlandish and contradictory hypocrisies that so obviously prove the fuel for much of his writing and speaking.

Curious too, that Yiannopolous also makes similar claims of his own race, ethnicity, and orientation, that of a gay Jewish man (or half-Jewish, if these distinctions are critical.) And yet, in Baldwin’s case, this outsider’s perspective proved the test of his spirit, in which he has come out victorious, immortal, a voice for the ages. In Yiannopoulos’ case, we see that the ingredients were insufficient, the product half-baked. (Indeed, any comparison is indecent and unmerited. Yiannopoulos is no Baldwin. He’s not even a Mailer.)

There is no more obvious trait of Baldwin’s, in his writing and speaking, than something that can only be called a spiritual maturity. Baldwin’s gentle yet fearless reckoning with the past and implied future that so clearly preoccupies him. He appears wiser, more complete and self-reflective than any of his antagonists, serene but immovable, willing to reckon with their blind spots like a patient teacher, then turning to demolish their arguments with a single, incisive blow. In Milo’s case we see the reverse: despite his most deft turns of phrase, his cleverest slip of the cuffs, the one impression you aren’t left with is a sense of his sincerity. This goes beyond the uncanny feeling that he simply doesn’t believe what he says. We intuit, on some layer just beneath the veneer of insouciance and bad posture, that he dislikes who he is, that he hasn’t earned comfort in his own skin.

The first time I saw it, the Baldwin/Buckley debate video opened a new world for me: a vigorous sustained debate between intellectually matched (or perhaps outmatched) opponents. Though Baldwin did not have what you might call a “home field advantage” at the Cambridge Union, he does finally and fully by the force of his arguments claim the support and adulation of the crowd. There is a remarkable feeling that descends on the proceedings around the 38:00 mark, where the audience spontaneously rises to their feet and offers Baldwin sustained applause, the television announcer breathlessly relaying that “this is the first time this has been recorded in the history of the Cambridge Union,” and Baldwin, clearly surprised and very suddenly the only one still seated, breaks into an unscripted, victorious grin. Buckley, for his part, knows, unmistakably, that he has been soundly defeated. This moment is as invigorating as any in the history of cinema.

This was the force of his ideas. This is the force of ideas.

So, on hearing that Yiannopoulos, seen by many as the new direction, if not the new face, of the Trumpist movement, has been invited onto Real Time with Bill Maher, an HBO weekly program with a weekly viewership in the millions (in which I include myself) I see a challenge and an opportunity.

A moment to reflect on what Yiannopoulos is: Though he self-styles as a kind of conservative gadfly who targets liberal cultural pieties like modern third-wave feminism, #BlackLivesMatter, gender identity, campus activists/so-called ‘social justice warriors (SJW’s)’ and other familiar cultural flashpoints and somewhat-easy targets, he is mainly famous for embodying a kind of grimy, take-no-prisoners approach to argumentation with his adversaries that encourages below-the-belt tactics such as ‘doxxing’ (publishing personal information about his enemies), tweetstorming, brigading and encouraging his legions of very loyal followers (so-called “trolls”) to personally harass and attack the targets he names online. This was most recently done to Ghostbusters star Leslie Jones for the crime of being what Milo found unattractive. Jones reportedly has since withdrawn from Twitter, but his style of attacks certainly have not been limited to her. The list of victims is long, and the tactics shameful and absurd.

As a consequence of his notoriety, Milo became editor at Breitbart, a website with visitor counts in the dozens-of-millions per month, and was ejected from Twitter with upward of 300k followers. Surely by now he would have more. You can choose to ignore him, but his stature is, unfortunately, real. Our task is to help it remain brief.

Because Milo interweaves legitimate, hard-hitting criticism of fair-game topics, this provides him with enough cover to perform his shtick as a presentable and sincere opponent. He volleys specific and cited claims in-between ad-hominem remarks and stabbing insults, so the switches in register and content can be difficult to follow, the fact-checking delayed. Many close examinations of his claims find that they simply don’t hold up under scrutiny, but enough do to make a there, there. Fine.

Accordingly, the media hasn’t really known how to handle him, and this is where he has been at his most deft and manipulative. He understands the way technology and new communications platforms work. Social media doesn’t lase, it ricochets. It’s functionally impossible to hold any kind of serious debate in 140 characters or less, you can only trade jabs and generate attention, ricochet from one platform to another, a 5-minute media appearance here, 140 more characters there, article here, YouTube video there, a Podcast appearance here, a college tour there, with riots, and a Hannity appearance this time loaded with video of the riots to make the point about his radical and uncontrolled opposition, the true antagonists to free speech. Repeat sequence.

Given the tools, the trained fracturing of attention, the inability to hold conversations — this is simply the best moment in history to generate attention through controversy. I submit that Milo is one of a new kind of media creation, what I call a “Troll King,” supported by a pyramid of followers, covered by the wreckage of his guerrilla-style podcast and YouTube appearances and remarks, surprisingly bereft of substance and easily confronted and revealed head-on. A reality TV star with no reality show. A smoke monster. Famous, but mostly just on the internet.

A word on classification: it also seems clear that Milo depends, to a great deal, on the heated response of his opponents as the engine of his fortunes, and having been (mistakenly, in my view) grouped in with the hard Alt-Right movement as a fascist has done more for his publicity than anything he has personally said or written. In a recent Chapo Trap House interview, writer and scholar of the Alt-Right, Angela Nagle, points out that although his entire shtick is about lashing out at SJWs, he depends on liberals, he loves liberals, he would be nowhere without liberals. Like a Satanist without the Christian Church. He isn’t actually a Fascist or even a member of the so-called Alt-Right. (“Those people have me on a hit list,” Milo has observed.) “They all love Trump,” says Nagle, “that’s one thing that unites them completely, but they are bitchy and sectarian… [white nationalist Richard] Spencer and Yiannopolous hate each other a lot.” “He’s not Alt-Right, he’s [what some call] ‘Alt-Light.’” “Basically they don’t have a program that concentrates on race, whereas the hard Alt-Right includes segregationists and really stresses race.”

Milo has no platform. Spencer and his wing’s interests are by contrast political and long-term. “The Alt-Right is identity politics for white people,” Yiannopoulos says, and I’m against any kind of identity politics, so you should drop them.” Clearly, Milo is as confused as anyone that he is grouped as a member of an ideology that he claims to reject and whose members clearly reject him. The Chapos point out that the Alt-Light: the Gavin McInnes-es, the Milo Yiannopouloses, are basically a reaction to modern liberal sanctimony, a punk-Howard Stern reaction they call a “transgressive lifestyle brand.” On Maher, Milo casually referred to himself as “just a pop star.”

So liberals do Milo favors by making him into a Fascist Lex Luthor figure. He has laid some answerable arguments at liberals’ feet, and a fact that we ignore at our peril is that for many, these punches have landed. You don’t just gather up millions of followers by targeting feminists with doxxing attacks. Some of what you say has to make recognizable sense, if the message is to take. Something I will credit Milo with is that he is clear on his positions and disarmingly honest about what he thinks his weak points are. He does liberals the very good turn of explaining exactly what charges they would need to answer in order to prove him wrong. And millions apparently agree with him, beyond just finding him entertaining.

This is something we liberals need to contend with, beyond just de-platforming, protesting, and preventing him, which defer the same ideas to the next Milo-like object: diseases aren’t killed by quarantine, only delayed. This is where I return to Baldwin’s example of substantive intellectual demolition. Will there be another Milo, after Milo is gone? Yes. But notice no one is debating the question “Is the American Dream Presented at the Expense of the American Negro” anymore. That one’s been answered. It is indeed possible to close a conversation to the satisfaction of most. Let’s not hide from that we can shut down. The answer isn’t “I won’t share the stage with that person.” The answer is, “See you Friday night, kid.”

Yiannopolous’ willingness to appear on Real Time sounded to me like the basis for a debate, of at least a confrontation constrained by the norms of conversation, the opportunity for a takedown of his ideas. Corner him, leave no room to fire a tweet and leave. Here’s that appearance:

You don’t really need to watch this.

Now: I know this sounds old-fashioned, the equivalent of “I’ll-have-my-seconds-call-for-you-at-dawn” in the social media era, and perhaps even wishful thinking that the Troll King should play by the rules of conversation. Practically speaking, outside of PBS and YouTube, we don’t have long-form discussions that anyone on the left or right watch with any frequency. Admittedly, I’m struggling mightily to elevate the forum of an HBO comedy show. This is what we have to work with, now. Maher’s is an hour-long panel show with a YouTube-only segment called Overtime. With the right presentation, this could provide a stage for such a conversation, and it would inevitably be excerpted (with the word ‘DESTROYS’ in the title) on YouTube. The salient bits would be available to be searched in perpetuity, in the same place and same way that made Milo famous in the first place.

Debates can appear to be lost in real time but won over the longer term. The truth will always come out. Once the fact-checking is done, someone is right. People love a jab, a joke, a good set-up. But in the end, most follow who has the facts. (This may not be in time for an election, by the way.) YouTube videos are, essentially, forever.

At first, it appeared this confrontation wasn’t going to happen. One of the scheduled panelists, leftist author and conflict reporter Jeremy Scahill retracted his attendance, offering a hangdog letter that explained why he could not share the stage with a person like Milo. Scahill has every right to manage his career, brand and frankly, ethical commitments, but the only way I’d see this as useful was if Scahill knew the person who would replace him was at the rhetorical level of a Baldwin or a Hitchens. In my humble opinion, the left isn’t producing a lot of these right now, for precisely these reasons: we have shied away from the intellectual battles that would have sharpened us. So as Bill pointed out in his response, this was Scahill’s loss. Ceding the territory doesn’t put you above the fray. We have a word for this, and the word is ‘forfeit.’

Maher responded to Scahill’s charges insisting that the truth would come out, and that there could be no better response than to have Milo ‘exposed.’ “Sunlight is the best disinfectant,” he would later say.


Almost everyone agrees that Bill went too light on Milo that night. The Washington Post even called it a “Bromance.” I’m going to give Bill a slight pass on this one: he needs to have guests on his show who are willing to come on without anticipating an ambush or unfair treatment — the smart move is to outsource the actual combat to his panel. He should have guests on that are going to challenge each other while he maintains his ability to keep the conversation moving. But yes: Bill seemed unprepared, without specific arguments of Milo’s that he wanted to tackle or controversies he wanted an answer about.

And this is where, I suspect, most TV critics failed to do their homework. It was in the “Overtime” segment posted to YouTube the following day, that the promised fireworks finally emerged. Guests Larry Wilmore and Malcolm Nance were left to challenge Milo, as overseen by Maher. In the Q&A format, Milo was able to really let loose, and become provoked into far more specific baiting and leading. When the conversation once again veered towards where transsexuals should use the bathroom, Milo was only too happy to take it further, going after Caitlyn Jenner, calling trans people victims of a “psychosexual disorder,” and finally levelling the bizarre and unsubstantiated claim that they are disproportionately involved in sex crimes (true, but only if you mean as victims). When Wilmore pointed out that these were the same unfounded charges generically made against homosexuals (like Yiannopoulos himself) years before, that they were perverts and that homosexuality was a disorder, Milo replied, “Maybe it is.”

This is where Maher did seem to lighten up on Milo, and perhaps give him too much of a break. However, it did seem that he was trying to pull him back from the precipice when he said, “You remind me of a young, gay, alive Christopher Hitchens, but you gotta lose that shit… People are just beginning to hate you,” he continued.

Again, the defining, remaining image was not that Milo was particularly incisive, or hard-hitting, or really leveling anything like a real challenge to anything but the well-documented excesses of zeal on the left; beating on a tired strawman. By virtue of the protests, the editorials and controversy, he had been made to seem bigger than he was. Laid bare in YouTube conversation with B- and C-level celebrities, he seemed to reach no greater classification than “classic prick.” If anything, it was so obvious, that one wonders how he got on the show on the first place. And that’s the point. It’s one thing to suspect that the dark emperor has no clothes, it’s another to lay it out.

And yet, consider all of the heat that Maher took, before and after, for having the temerity to have this person on the show. Liberals and progressives were winding themselves into knots to confess how they never liked Maher, have been suspicious of him and his lunatic crusades, that he was too easy on Milo, that in having Milo on, Maher “mainstreams hate,” he’s no longer liberal, that he’s failed to change with the times, and on, and on.

What happened? We used to be the party of debate. Maher scanned the crowd of liberals for a champion and unfortunately, came up short. Our response, once again, was to respond to the invitation with calls for intellectual quarantine.

Liberals used to see an opportunity like this and glove up for the fight, not for the fight that prevents the fight from happening. Am I the only one who sees an opportunity like this and doesn’t think “stop mainstreaming hate,” but rather “I can take that guy.” Who from the liberal side should have, could have, would have been the knight on the progressive side to meet Yiannopolous, jab for jab, in the field of open discussion? Jon Stewart? Is there anyone we would have tolerated attending in the first place? Or are we just above it now? Why do we shy away from, de-platform, contest, protest and simply avoid that which we should run to assert: an opportunity to declare, finally, and forthrightly, what our values are, assertively, dominantly, conclusively? Or are we just out of practice?

Watch the Baldwin debate. This is who we were. This is who we need to be, again.

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