The Last Days of the Boy Masterminds

The internet was their playground, Milo Yiannopoulos their cheerleader.

Photo: Jared Tarbell

You know the boy mastermind of the internet: snarky and full of himself, a know-it-all shielding his insecurities behind the anonymity afforded by cyberspace. Heck, maybe you even were a boy mastermind, back when the web was young and uncivilized. But his natural habitat has become crowded with “normals” and “sensitives” — types he probably thought he had left back in the real world. Much to his chagrin, the “IRL/URL border” has become much more permeable since the age of Mosaic and Netscape Navigator, and what was once a simple turf war has transformed into a bitter rearguard struggle to preserve a piece of a rapidly vanishing past. Now only one boy mastermind claims to stand in the way of his culture’s looming extinction.

That great self-appointed champion of this disappearing homosocial order is Breitbart provocateur Milo Yiannopoulos, who waded into the fray with attacks on feminists he believed were politicizing a world of computer gaming that had long been the province of men — and particularly of boy masterminds. Milo laid out his case succinctly enough, telling women who were bothered by the old and nasty internet to simply “log off” and let the boys have their vicious fun. Milo is himself a boy mastermind of the highest order, an online bully who earned a Twitter de-verification, a temporary account suspension, and finally permanent banishment for his insulting tweets and harassment campaigns.

Milo’s departure should come as no surprise to most of us; given a choice, the boy mastermind always opts for anti-social media. Milo appears to have every intention of remaining on the fringes of the mainstream, relying on his wild antics to draw attention from passersby with much more serious and important things to do. But as with any lost cause, Milo’s quest to preserve mastermind culture does raise an interesting question: is this something better left abandoned and forgotten?

Drive through the rural southwestern corridor of Pennsylvania and you will see many Confederate flags on display. This has always struck me as curious, since Pennsylvania fought for the Union. But that flag is no longer a show of support for a rogue state; it is, rather, a nostalgic emblem of a make-believe era when society was static and people knew their place. Milo and his ilk are similarly invoking a halcyon vision of a benighted time when, as bad as things were, they at least had a special and secretive room of their own.

I entered that private room when I was eleven. My family connected to the internet in 1993, and the version of it that I encountered through the Mosaic web browser struck me as an ugly, confusing place. It lacked meaningful curation and was navigated mostly through primitive impressionistic path-finding, with the user directed from one pile of black text set against a white background to another. Images could be displayed, though even the most low-resolution image took an eternity to load (in spite of that limitation, smutty pictures and other vulgar content soon began to accumulate on FTP servers). In time, I discovered bulletin boards and forums relevant to my interests — comic books, wrestling, weightlifting — and immediately started engaging in pissing matches with other awkward loners studying those subjects.

This early internet was a kind of messy bachelor pad, and the boy masterminds abounded. Each of us had independently discovered the web, as we had done with Roger Corman films or post-punk music, and we manspread across this open frontier. And it was male-dominated terrain in those days, in principal part because of a process of acculturation that still equated computer technology with “nerds” and discouraged women from participating altogether. There was a running gag about the AOL chatrooms, in which parties exchanged wholly fictitious a/s/l information with one another, that such conversations inevitably devolved into two men who were pretending to be teen lesbians “cybering” with each other.

This was the golden age of the boy mastermind, a time when regular usage of the internet coupled with a poorly designed Geocities homepage was sufficient to cause your out-of-touch parents to label you a “techie.” The multifarious harassment methods perfected in later years by the likes of 4chan and 8chan were still in their embryonic stages, but they were no less trauma-inducing. mIRC, in particular, was a bloodbath: I recall vicious mastermind competition for chatroom status that led to the creation of special password-locked rooms for private cliques, empty boasting about physical and sexual accomplishments, and seemingly endless attempts to “dox” (discover private information about one another, up to and including posing as someone else, usually a woman, to score nude photographs) and “break” (i.e., trigger some kind of serious mental breakdown) our rivals.

As this rough-and-tumble culture coalesced, it would prove a useful vehicle for media outlets looking to increase viewership via scary stories directed at flyover country. The Columbine murderers Dylan Klebold and Eric Harris, who played the bloody first-person shooters Doom and Quake together, were villainous boy masterminds straight from central casting: a two-man “trenchcoat mafia” who conspired to wreak vengeance on their normal high school classmates. After Columbine, the boy mastermind became more than just an outcast; he was now a suspect, too.

With the bursting of the dot-com bubble in 2000, the boy mastermind started sharing his space. Various companies were aggressively trying to recruit internet users, and internet speeds increased beyond the limitations of dial-up modems. But by 2004, the boy mastermind surely saw the writing on the wall. All kinds of regular folks had logged on, and not just to arbitrage their store-bought Beanie Babies on the eBay market. Now the boy mastermind was faced with a fast-rising wave of people, including women and older adults, weblogging about their feelings. Not only that, but content that these people might want to read was migrating online too. Where media and newspaper websites had once been mere bookmarks amid a sea of fanfiction and other DIY material, they were now integral parts of those businesses.

Where once all the virtual world had been men, it was at first slowly and then suddenly a place for everyone else. Eventually stories about grandparents having blogs ceased to be novel; eventually they ceased to be stories at all. And so the boy mastermind retreated further, moving his shitposting and harassing operations to text-heavy forums that recalled the bare-bones internet of yore.

Social media made things worse for the boy mastermind. Friendster and Myspace began allowing users to associate faces with names, lifting the veil of anonymity. Facebook and Twitter universalized the process, creating privately owned landscapes where second lives collided with, and eventually just became, first lives. Boy masterminds still linger on these sites, but their anonymous accounts and hateful shitposts are increasingly anomalous on a publicly monitored internet more inclined toward polite speech and thoughtfully constructed identities.

They’ve lost their games and comics, too. Now that nerdy popular culture is just plain old American monoculture — all Avengers, Pokémon, and Dungeons & Dragons. The boy masterminds find themselves having to accommodate an influx of minority characters, game designers, authors, illustrators, and programmers. The response led by Milo boils down to an angry won’t-you-girls-leave-our-stuff-alone plea, and the process they’ve critiqued is inexorable. The internet is more populous and diverse than ever before, and individual users have differentiated and diversified themselves to stand out. Even Milo is a unique product: a flamboyantly gay, ethnically Jewish men’s rights activist and self-professed Donald Trump fanboy speaking on behalf of an aggrieved mastermind community that includes scores of unrepentant homophobes and anti-Semites.

But is the culture that Milo champions deserving of preservation? No more than the culture of the Confederacy. Both are historical facts that ought to be remembered, and the activities of their present-day supporters warrant a certain degree of scrutiny, but neither represents a way of life that has any place in the modern world. Milo portrays his fellow boy masterminds as warriors who succumbed to a force greater than their own. But that’s a load of malarkey: they are just losers, and it’s time for them to get lost.