From Andrew Ross Sorkin in the New York Times DealBook:

A billionaire Silicon Valley entrepreneur was outed as being gay by a media organization. His friends suffered at the hands of the same gossip site. Nearly a decade later, the entrepreneur secretly financed a lawsuit to try to put the media company out of business.

That is the back story to a legal case that had already grabbed headlines: The wrestler Hulk Hogan sued Gawker Media for invasion of privacy after it published a sex tape, and a Florida jury recently awarded the wrestler, whose real name is Terry Gene Bollea, $140 million. What the jury — and the public — did not know was that Mr. Bollea had a secret benefactor paying about $10 million for the lawsuit: Peter Thiel, a co-founder of PayPal and one of the earliest investors in Facebook.

If ever there were a case with no one to cheer for, this is it: Gawker does do good work, but they do really terrible things as well, and their outing of Thiel despite his explicit request not to is indefensible. It disgusts me, and my disgust is only deepened by the moralizing and righteousness of the post in question, as if Gawker has the right to make the most personal of decisions for anyone.

It is also legal and protected speech.

Thiel, meanwhile, is being a bully of the first order. He is attempting to run Gawker out of business — this lawsuit he is funding is one of many, and he has lawyers looking for more — in part because he can, and in part because he has styled himself as a twisted version of Batman: a vigilante who is not so much above the law (what he is doing is also perfectly legal), but rather one who uses the law to first and foremost avenge himself even as he spins a story about his defense of the vulnerable. Thiel told Sorkin:

“It’s less about revenge and more about specific deterrence,” he said on Wednesday in his first interview since his identity was revealed. “I saw Gawker pioneer a unique and incredibly damaging way of getting attention by bullying people even when there was no connection with the public interest.” Mr. Thiel said that Gawker published articles that were “very painful and paralyzing for people who were targeted.” He said, “I thought it was worth fighting back.”

Mr. Thiel added: “I can defend myself. Most of the people they attack are not people in my category. They usually attack less prominent, far less wealthy people that simply can’t defend themselves.” He said that “even someone like Terry Bollea who is a millionaire and famous and a successful person didn’t quite have the resources to do this alone.” Mr. Thiel said that he had decided several years ago to set his plan in motion. “I didn’t really want to do anything,” he said. “I thought it would do more harm to me than good. One of my friends convinced me that if I didn’t do something, nobody would.”

What a hero.

The Conditions of Superheroes

In one of the more thought-provoking essays I have read all year Brian Phillips put his finger on how comic book hero movies have, in his words, “become vehicles for talking about larger social issues”, particularly the exercise of power in a post 9/11 world:

In the world of these films, there were no mutants or “enhanced humans” or benevolent alien overseers within living memory. Society was more or less just like our society. Then superheroes arrived. A line was crossed. Things changed. There is always, in these movies, a sense that the world has gone a little crazy, that we are dealing with a new order whose rules no one really knows. And that newness partly explains the extreme focus on the problem of whether and how the abilities of the heroes can be accommodated within the existing framework of governments and laws and the popular will.

The other explanation for that focus is an irony that, when you start to lay it out, is kind of gobsmacking, and that gets at an almost Greek-tragic dimension of recent comic-book movies. (Let’s say Norse-tragic, because Thor.) The irony is this: The superheroes in superhero movies are always the only force capable of saving humanity from the threats it faces. But with astounding regularity in post-9/11 comic-book films, the threats mankind has to be saved from were either unleashed by the heroes themselves, came into being simultaneously with the heroes, or both. In other words, the chaos from which the heroes are required to save the world is implicit in the heroes’ being in the world in the first place; even when the protagonists aren’t actually the authors of the crisis they are fighting against — something that, again, happens with startling frequency — they are manifestations of the same fundamental shift.

From this perspective, it could not be more perfect that Thiel made the largest part of his fortune by investing in Facebook, where he still sits on the board. Facebook specifically and the Internet broadly has made it possible for sensationalistic rags like Gawker to exist, even as it has fundamentally weakened journalism by destroying the geographic monopolies that guaranteed the financial freedom to comfort the afflicted and afflict the comfortable. Thiel as the personification of the tech industry is very much the superhero looking to remedy a problem he created.

Vigilantism and Unintended Consequences

And so, as is the case with the superhero movies Phillips describes, who you think is right depends on your perspective. Narrowly speaking, it is hard to fault Thiel — hell, the fact he was willing to wait eight-and-a-half years to exact the revenge he promised Gawker publisher Nick Denton should he out him is almost admirable, and in a weird way likely explains why Thiel has such an unbelievable track record as both an entrepreneur and investor (Paypal and Palantir as an entrepreneur, Facebook, LinkedIn, Yelp, Stripe, Yammer among many others as an investor). Gawker did him wrong and he is exacting his revenge on a time scale far more expansive than Denton likely thought possible.

Again, though, Thiel has already won. He is fabulously wealthy and extremely influential, and say what you will about Gawker, the liberal democracy that made it possible for the companies Thiel has built and invested in to emerge depends on a free press; driving a publication to bankruptcy via lawyer fees may be legal by the letter of the law, and even deserved on a personal level, but it is in absolute violation of the spirit of the law and, I might add, a rather hypocritical — or is it ironic? — use of government by the avowed libertarian Thiel. What are more concerning, though — and implicit in this concern is a critique of libertarianism — are the second and third-order effects of Thiel’s approach.

The most obvious second-order effect is that, as Felix Salmon writes, Thiel is providing a blueprint for the suppression of the press by the wealthy. But what concerns me — and what ought to concern Thiel, and all of the Silicon Valley elites celebrating his actions — are the third order effects. Specifically, Thiel’s actions are bringing into stark relief the fundamental weakness of old analog businesses like journalism relative to the incredible power and strength of the technology sector, and if companies follow Thiel’s example, the freedom that makes the emergence of said companies possible could quickly come under threat — and deservedly so.

Consider Facebook: I have argued strenuously that the idea of Facebook consciously abusing its unprecedented power over what people see is absolutely a problem in theory, but one that is contained by Facebook’s own incentives and the fact that the alternative — government regulation of speech — is even more undesirable. At the same time, I am troubled by the societal impact broadly of Facebook’s efforts to be neutral via algorithm and the potentially destructive impact that has on our politics in particular. What is truly alarming, though, is the prospect of a company specifically and an industry broadly that is convinced of its own righteousness, unconscious of its own power, and blind to what it doesn’t know, making decisions with unintended consequences — like outing LGBTQ people at scale.

Truthfully, though, Facebook is one of many (and has proven itself to be rather benign, in my estimation). You don’t need to go a block in SOMA or a mile down El Camino Real to encounter any number of companies full of people attracted by shared backgrounds and experiences that are “changing the world”, fueled by little more than a cult-like devotion to mission and a bank account full of money betting on the market-monopolizing effects of Internet economics. And — this is the scary part for the industry — the more those companies are not just successful, but abusive in their obliviousness to the societal impact of that success, the greater the likelihood that the only possible countervailing force — the government — will have no choice but to give in to the certain backlash and interfere.

In other words, the avowed libertarian is, in some small way, showing the way in which the government interference that he claims to detest might come to bear — as a response to unconsidered abuses of power — all in the service of settling scores made possible by the industry that made him rich.

Power and Responsibility

Here’s the fact of the matter: what Gawker did (and still does) is wrong, but it’s wrong in the way that — and forgive the seriousness and political nature of this analogy, but I think it captures my point — Saddam Hussein was an awful dictator who murdered his own people. Taking him out may have been satisfying and justifiable in a narrow sense, but at what cost to the United States in both treasure and broader legitimacy?

The tech industry, like Thiel, is no underdog: it is the dominant economic force not just in the United States but in the entire world, both because of the wealth it creates, but especially because of the wealth it destroys. And, to quote another comic book figure, “With great power comes great responsibility”.

In this case, no matter how badly Thiel was personally hurt by Gawker, or how morally wrong their actions were, he is the one with far greater power, and the appropriate approach is not to leverage said power in an act of vigilantism, but to exercise the responsibility of defending the conditions that made his power possible to emerge, conditions that I believe are to the long-term benefit of everyone. That would be an approach worth applauding and emulating, not just because it’s the right thing to do, but because the freedom that made possible the tech industry that made Thiel rich depends on it.

UPDATE: I tweeted a follow-up to this article here. Please read it.