The Art of the Virtuous Troll

You remember this interview, right? Back in summer 2016, just after Milo had been banned from Twitter for trolling Leslie Jones over her trawling for sympathy over the bad reviews of Ghostbusters, ABC sent an interviewer to London to find out wtf Milo thought he was doing.
ABC: “Are you a troll?” 
Milo: “Of course.” 
ABC: “What is trolling? How you do you look at it?” 
Milo: “I like to think of myself as a virtuous troll, you know. I’m doing God’s work.”
The ABC interviewer was incredulous. A virtuous troll? Surely, this was yet another of Milo’s despicable not-funny jokes. How could saying that a woman looks like a dude be virtuous? Would Milo say that to her face?
Milo [nodding]: “Yeah, probably. I probably would.”
Go, watch. The expression on the interviewer’s face is priceless. But, of course, he never lets Milo explain, just calls Milo an idiot, and moves on to ask why Milo didn’t stand up for Jones against the whole of the internet—implying that it was Milo’s fault other people were responding to her tweets.

Milo was having none of it.
Why should I have to police other people’s speech? I am responsible for what I say. I’m perfectly happy to tell you I think that stuff [like calling Jones an ape] is disgusting....  Trolls are the only people who tell the truth these days.
So, it would seem that the virtue of trolling has something to do with telling the truth. But why does truth-telling need trolls? Wouldn’t it be better simply not to lie?

Well, that depends on what kind of lessons you are trying to teach.

It is one thing to tell the truth. It is another to get people to see it. It is wholly another to get them to change their behavior so that they are no longer living a lie.

Take, for example, the trolling of Nick Monroe.

You don’t follow Nick Monroe? Neither do I except accidentally (see below), but before he was banned from Twitter this past May, he had upwards of 50k followers—and he will never let you forget it.

Like Milo, he is now in exile from Facebook, Twitter, and Instagram over on Telegram, where, unlike Milo, he talks incessantly about getting his Twitter back.

Like Milo, he also set up a Telegram chat room where his fans could interact directly with him.

Unlike Milo, he doesn’t have a chat room anymore.

Why? Because Milo nuked it with the help of two of Nick’s own admins.

On the night of July 31, all 1,212 members of the Monroe Newsroom vanished—deleted laboriously one-by-one by the admins whom Milo had instructed to carry out the troll. It took hours, while we in Milo’s chat room watched with glee (Milo shared screenshots), knowing that Nick would wake up and find everyone gone.

It was glorious, particularly when Milo invented a persona for himself posing as one of Nick’s fans who kept asking where Nick was and wondering why everyone else was leaving.

Needlessly cruel? Or a virtuous troll?

Here’s a hint. Oblivious as he was to the deletions the night before, Nick knew immediately what had happened to the chat—because Milo told him. Trollishly, of course.
MILO: Not sure why Nick Monroe would abruptly kick everyone out of his chat like that, but DM me at @miloinc and let me know why you should be let into my secret FAG PALACE and I am happy to accommodate some digital refugees. 
That boy, honestly! The Twitter ban must really have got to him.
And, of course, there were screenshots, which Nick shared on his Telegram channel.

Nick’s response:
god damn it milo
You’re a fucking psychopath
I wanted you to teach me how to write better
And yet, to date there Nick is, still pining for his Twitter account—and not writing anything except Telegram posts.*

The clues are all there. Can you see them? What made Milo’s trolling of Nick Monroe and Leslie Jones a virtuous troll?


1. Own it. When Milo trolls, even from behind a mask like his Twitter avatar @nero or with the help of others, he does so in such a way that it is utterly clear it is he doing the trolling. Just as he told the ABC interviewer, he is responsible for his own words, which means, he takes responsibility for his own words. It is true that women often take things said about them on the internet more personally than do men so that women often take offense at things even people known to them say (see Leslie Jones), but the greatest difference between a common or garden troll and a virtuous troll is responsibility. When push comes to shove, do you own it as yours? Do you take responsibility for your own speech? 

2. Be humble. Milo jokes about how fabulous he is all the time, but notice what I just said: he jokes about himself. To be a virtuous troll, you need to be willing to make yourself part of the joke, just as Milo did with his faux persona during the trolling of Nick. Such self-deprecating humor is the essence of generous comedy: get the audience laughing with you by being willing to laugh at yourself. But it is also the essence of virtuous trolling. You want to make somebody else feel ridiculous? Be willing to be made ridiculous yourself by becoming part of the joke.

3. Use allies sparingly. You may say that Milo was cruel to turn two of Nick’s admins into his agents for the troll, but note that there was no mob. Milo most emphatically did not invite those of us laughing in the chat room to join in the troll. He shared it with us because he enjoys showing off how clever he is (and he is!), but the point was not to have us gang up on Nick, but to let us see what he was trying to show Nick as a lesson to ourselves. Virtuous trolls do not work in packs; packs are for cowards like Antifa (see number 1).

Corollary: Use minions lovingly, and provide them with gifts to convey, not insults.

4. Give your target an honorable out. A virtuous troll is something that the target should be able to recognize as a joke in which he or she can share. Note that even Nick seems to have gotten the joke. The trolling did him no material harm—it was just a chatroom, nothing to do with his actual occupation. The point was to make him embarrassed for caring so much about a chat. The point, in other words, was to puncture his pride—so that he could move on to writing the proper journalism that Milo had offered to help him with. Nick even admits it: “MILO, I wanted you to teach me how to write better. You can do that WITHOUT BLOWING MY SHIT UP.” No, Milo couldn’t—because as long as Nick is focused on the ephemera of social media and the faux popularity of “likes,” he will never develop the discipline he needs to write something more substantive. Milo was trying to teach him to laugh at himself so that he could become a better writer. The virtuous troll wins when the target laughs at him or herself (see number 2).

5. Troll for joy. The purpose of vicious trolling—the kind that the ABC interviewer assumed Milo practiced—is to destroy morale. It is to scare the target, not just make him or her feel a bit embarrassed. The purpose of virtuous trolling is to teach the target a lesson that will enable him or her to grow.

Why did Milo point out in his tweets to Leslie Jones that she was “Barely literate”? Because her tweets were ungrammatical. Milo wants her to do better than that. Why after she had his account blocked did he tweet “rejected by yet another black dude”? Because, on the one hand, Milo loves black dudes (and it is funny to imagine any of them rejecting him—see below); and, on the other, Jones was tweeting about being upset that a movie in which she, in effect, played a man (or what had been a man’s role in the original Ghostbusters) had been getting poor reviews for not being as good as the men’s version (Milo explained why in his review: in part, it was because the scriptwriters gave Jones such a caricature to play.)

Milo wants Nick to learn a similar lesson: that he has been trying to play a role on social media that demeans him, is unworthy of his talents, and will not further his career. Such lessons are often painful to learn, which is why simply telling people the truth doesn’t work. All of their rationalizations for staying the way that they are kick in—“Twitter will take me back if we make a big enough protest”;  “My Twitter feed was a source of real news; I don’t need to change the style of my journalism”; “I wouldn’t be having these problems if other people would just support me the way that they should”—and nothing changes.

Been there, done that. Just ask me how I feel about wearing makeup for going on camera. Or what it was like getting over writer’s block the last time I started a big new book. Or any number of times that I refused to acknowledge what I needed to learn in order to fence. What did it take to jolt me out of my rationalizations? Being willing to laugh at myself and take the hits—just like Milo wants Nick to do. Just like Milo is willing to do himself by playing the fool.

Now, don’t you wish Milo would come troll you?

 For my continuing adventures with Milo, see The MILO Chronicles.

*[UPDATE August 29, 2019, 3:07pm: Just now on his Telegram channel, Nick helpfully shared the fact that at the very same time I was working on this post yesterday (see screenshot above) he published a new piece on GamerGate. Go, Nick! So glad to be proven wrong about your work!]**

**I am actually a bit spooked at the timing here. I swear, Milo is magic. The coincidences are too great to explain otherwise.


  1. Just finished reading @RachelFultonBrown's "The Art of the Virtuous Troll," and I thought I'd add some perspectives from Jewish theology. If you prefer not to read material from another faith tradition, that's completely understandable; some people find it interesting, and others simply prefer not to be distracted.

    When Wrong is Right, and Right is Wrong
    Jews (well, observant Jews) learn about giving reproof from several key sources. The first is the Naviim (Prophets) and the story of Penina and Chana (Hannah). Chana is childless and miserable. Her "sister wife," Penina, teases her about her childlessness in order to motivate her to pray for children. Penina's actions are successful; Chana prays that G-d will bless her with a child; and she gives birth to the Prophet Shmuel (Samuel).

    So was Penina wrong to tease Chana? Or was she correct to tease Chana in order to spur her toward more intense prayer? The answer to both question is "Yes." We are taught that Penina was both right and wrong: her actions remained wrong even though they were purely motivated and resulted in success.

    But a logical person would obviously ask, "How could an action that results in virtuous behavior be considered 'wrong'?"

    The answer is that sometimes we must do things that are wrong. In fact, sometimes G-d even commands us to do things that might be considered wrong. King Saul was punished in his lifetime and even beyond because he failed to kill the enemy king after battle, as G-d had instructed him to do. The enemy king had been captured, and Saul saw no reason to commit additional bloodshed -- to do so would be wrong. Yet a woman was smuggled into the enemy king that night, and she gave birth to a son whose descendents would torment Jews over millenia.

  2. **Choosing the 2" x 4"**
    There's old, old story about a man who must give his stubborn donkey a wallop with a board. But that alone does not make the donkey move; the man must then give the command. When questioned, the man explains, "The 2" x 4" is just to get his attention."

    Humans are every bit as stubborn as the most recalcitrant donkey. In fact, we generally take any and all advice except the advice we need most. Since Antifa has cornered the market on walloping people with boards, an effective but more subtle approach is needed.

    Much of Jewish writing and commentary gives advice on education, and one of the most famous lines is to teach your child "al pi darko" -- according to his path. Not your path, but his path. You must find the approach and techniques that will be effective for each individual. Education, formal or informal, is not worthwhile unless someone actually learns from it.

    **The Mussar Movement -- Self-Help Books Before Marianne Williamson**
    Another element of Jewish history and theology that comes into play is the Mussar Movement. This was a practice that was started in the 1800s in European yeshivas (post-secondary schools specializing in teaching Talmud). Each day, young men spent approximately 30 minutes learning various texts on how to utilize their time; control anger; conquer temptations, etc.

    However, actually improving in those areas was only part of the equation. The Mussar Movement believed that regularly studying materials on self-improvement had value in itself: by being forced to regularly reflect on the need for and benefits of improvement, people could make themselves more open to advice for actual, concrete actions in those areas.

  3. The Art of the Troll
    So how does all this relate to the righteous troll?

    Was it "wrong" of Milo to troll Leslie Jones or Nick Monroe? Probably. Was he "right" to do it anyway? Yes. Cognitive dissonance is our problem, not G-d's.

    How can Milo have been righteous in his trolling if it, like Penina's teasing, was technically wrong? Because the individuals would not have listened to sweetly-delivered suggestions. Like the donkey (and most of us), they required a forceful action to get their attention. The humor, the mild conspiracies, and Milo's marvelous self-deprecation (a uniquely British trick that Yanks can't pull off no matter how hard we try) serve to cushion the 2" x 4" that he uses to get his targets' attention.

    But righteous trolling is trolling "al pi darko" -- according to his path. Each unique trolling must fit the needs of the target. As Dr. Brown posits, the trolling of Nick Monroe was inextricably bound to his myopia regarding social media. Trolling him in some other way would not have been effective, since it didn't conform to his "path."

    Finally, as Dr. Brown also notes, there is the peanut gallery of online observers. Like yeshiva students studying Mussar, those following the troll from afar are being conditioned to accept correction themselves and reflect on their own foibles. At the basic level, an observer might self-correct his own behavior after witnessing the troll. I'm willing to bet that more than a few of us avoided checking our follower counts that night! At a deeper level, though, we were being trained to accept reproof -- a quality that is severely lacking in the world, and one that underlies all the world's great religions.


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