In the spring of 2011, tech billionaire Peter Thiel and Aron D’Souza, an ambitious young Australian lawyer, sat in a restaurant and plotted the destruction of Gawker Media. Thiel had been looking for a way to strike back at the company after he had been outed by its tech blog ValleyWag in 2007. D’Souza got Thiel to pledge $10 million to a secret plan to sue Gawker out of existence.

A year and a half later, Gawker published an edited tape of Hulk Hogan having sex with his best friend’s wife. Hogan sued Gawker with the help of Thiel’s fortune, and won a $115 million settlement that ultimately forced Nick Denton, the company’s founder, to sell Gawker Media and shut its flagship site down.

In his book Conspiracy, Ryan Holiday, the media critic for The New York Observer and the author of books on marketing and stoicism, presents an inside account of Hogan v. Gawker, based on interviews with Thiel, D’Souza (who is identified as Mr. A), and others. Conspiracy is the story of one of the most troubling and important episodes in the recent history of American media, with the twist that is sympathetic to Thiel’s motivations. I spoke to Holiday about Thiel, Gawker, and the larger implications of the website’s demise. This interview has been edited and condensed for clarity.

Thiel, in his public statements about the case, has argued that he ultimately moved to bankrupt Gawker because of a Valleywag post in 2007 that outed him as gay. But you present a more complicated set of motivations.

There’s a line, I can’t remember who said it: There’s always a reason and a real reason. In this case, it’s like four or five of those. The simple reason is that he’s a billionaire and he didn’t like what this outlet was publishing. The real reason is that they harmed him in a non-partisan but cruel and thoughtless way. The deeper level is that maybe there’s some economic motivation, maybe it’s raw power—a fight of wills. On an even deeper level it’s someone with the sense that “this is a pivot point and I’m going to take advantage of it—I can pivot history.”

When I marvel at what happened, I think we’re all responding to the same thing, which is that this guy really did crank the wheel. If this does have a chilling effect on media, which critics says that it does, that is still validating that hypothesis, which is that this guy thought there should be [a chilling effect] and he fucking did it, which is just insane. Nobody does stuff like that!

Rumor plays a big role in political journalism and business journalism. Much of what we know about the inner workings of the Trump administration is rumor. In business journalism, people who are trying to, say, short stocks often try to spread rumors. But Thiel seemed to be fixated on Gawker. Do you think that could have been because the site, to some extent, democratized rumor—that it wasn’t stockbrokers or political powerbrokers spreading rumors in media but ... regular people?

Edward Jay Epstein wrote a book in the 1970s about journalism that I found fascinating. One of the things that he writes that has always stuck with me is something like, “Journalists are dependent on sources and sources are inherently self-interested.” So whether you’re talking to The New York Times or if you’re reading a random piece of gossip about a celebrity, someone’s always got an agenda. One of the things that Gawker did that I think was particularly reckless was that it was indifferent to that agenda. The reason they don’t stop and think about publishing the Hulk Hogan tape is that their job is just to publish things, not to ask about the source of the information.

Gawker was dangerous because they would act like what they were doing was about transparency or truth, but was really subject to their own biases and their own manipulations. Its similar to how we were all optimistic about WikiLeaks but WikiLeaks has been corrupted by foreign governments, right? Thiel’s fear as a powerful person was: “What could these people do to me? What exposure do I have to the vulnerabilities this presents? A rumor could take Facebook stock down or something about my personal life could be [leveraged].” But then as a thinker-philosopher type he thought, “I have the resources to do something about this. Maybe I should!”

You are very critical of Gawker for not recognizing the conspiracy that it was facing. Why?

The final post on Gawker is “How It Works.” The running theme of the whole site—the way that they justified their existence—was that they were the truth-tellers, they said the things that other people were afraid to say, they dug into the sordid details that other people were afraid to dig into. As Thiel said to me (and he admitted it was histrionic, but there’s an element of truth in it), “What does it say about a media outlet that is supposedly dedicated to investigative journalism that it can’t investigate a conspiracy that’s happening to it in the present moment?”

The stories about Gawker’s investigative prowess were probably more marketing than anything else. What they really enjoyed was when these things fell in their lap: An anonymous tip or something juicy. Even in the case of the Hulk Hogan story, Gawker tried to present it like they were presenting this expose, this thing that was very much in the news—this thing that everyone wanted to know about. But the truth was that this arrived anonymously to them from a source, who was giving it to Gawker because he was trying to shake down Hulk Hogan. This lawyer was trying to use Gawker as a catspaw to embarrass Hogan and bring him to the negotiating table.

This argument that Gawker really understood how power works is preposterous given that they didn’t notice the conspiracy that was being wielded against them and that they were unwittingly being used by other powerful people with varying agendas—they couldn’t even see that. This story is about the ignorance of power and the consequences of that, as well as the understanding of power and its consequences.

Is this why, for much of Conspiracy, you present Gawker as the Goliath and Hogan as the David? One of the questions I had reading the book is how powerful Thiel thinks Gawker was and how powerful you think it was.

Generally, the media sees itself as the underdog. It is the underdog because their job is to speak truth to power. They also see themselves as this canary in the coal mine as far as authoritarianism goes. We want to be very careful that our right to free speech is never infringed upon and the media is the first line of defense.

Thiel at one point refers to Hulk Hogan as “only a single-digit millionaire,” which is a hilarious thing that only a billionaire could say. But what does it say that Hulk Hogan, by himself, almost certainly could not have afforded to take this case to trial and get the verdict that he got from a jury? We can agree or disagree about if it was the right verdict, but to get to that point where he won, it was otherwise impossible without Thiel’s backing. Yes, a lawyer could have taken the case on contingency, but that lawyer would have been incentivized to take the guaranteed $10 million settlement pre-trial—or wherever the number ends up being in this alternate universe. If that happens, Hogan never actually gets his day in court. We’re all entitled to this day in court, but he doesn’t get it without a billionaire’s help.

That belies the notion that the media is not the powerful one in this equation, at least in the beginning. Nick Denton judged that no one would be crazy enough to sue a media outlet and take them to court, particularly a gossip-focused one.

Sure, although this was never really about getting justice for Hulk Hogan, so much as it was about destroying the outlet.

Look, I view this story as kind of a Greek tragedy in that every element is exaggerated as far as it could possibly be exaggerated. That’s why I thought it was the perfect lens to discuss a lot of these things and to think about them and to make sure that we’re not taking our initial assumptions for granted.

What was never, for instance, bandied about in any of these settlement talks was an apology. There was no element of “Gawker needs to change.” So imagine if you’re Hulk Hogan and you’ve been deeply wronged and you want to be validated in a court of law. You want your actual day in court in the literal sense of the word. You’re going to have a hard time getting there because the whole system is based on “OK, we wronged you but we’re not going to admit we wronged you. We know you’re not crazy enough to take us to trial.” It’s this whole game theory thing where eventually it always settles on the courthouse steps. You can tell that Gawker felt that in the marrow of their bones: No case will go to trial.

Almost every strategic decision they made was wrong because they believed the case would never go to trial. And that meant that they also never had to seriously consider Hogan’s claims. I think what’s so fascinating about this is that Gawker thought they were winning for this entire series of events. But they didn’t win. It’s strange how we retroactively make them into sympathetic when they were not only convinced they were winning, but they were being bad winners as it was happening. They were taunting Hogan, they were waving the knife, bragging to the media about how ridiculous this is. It’s only when the surprise defeat happens and then two months later, when the real story comes out, that we retroactively change this as though they never had a chance the entire time.

One of the Gawker writers in their obituary basically says, “We live in a world where a billionaire can put a media outlet out of business and leave the defendants without legal representation.” That is about as objectively false as a statement can be. Gawker gets two cease and desist letters. Gawker runs the story knowing that Hogan is planning to sue whoever runs it. There are many settlements. Gawker is able to spend $10 million defending itself and only loses in a court of law.

I think that many of us—people who are genuinely pro-media—are aghast at the outcome of a billionaire putting a media outlet out of business. We need to make sure that our judgments about that are not blinding us to the facts of the case. Because facts matter and we can only learn from the facts if we agree on them.

Valleywag, the same Gawker-affiliated outlet that outed Peter Thiel in 2007, called you a “fraud” in 2014. How did that experience color your sense of the trial and its outcome?

The eulogies for Gawker would be like, “Now Gawker is snarky and mean, I’ll grant you that.” That’s much easier to say when you haven’t actually been that person. And when you haven’t experienced the baffling nature of having Gawker write something about you and then you run into Nick Denton at a party and he’s friendly. Then you realize that this was a mean thing that was done, but it’s almost made more senseless by the fact that they didn’t see it as mean. You toy with people because you don’t think that it’s real.

One of the ways that my own experiences shaped the book is that I think I had more serious empathy for what it must have been like to be Peter or Terry Bolea or one of the many people that they wrote about. These are nasty people in the Trump sense of the word. These are nasty people who enjoy that sense of antagonism.

But it also helped me relate to A.J. Daulerio on the stand, how painful that must have been. [Daulerio was the author of the post about Hogan’s sex tape.] He said, “I was in my own Gawker story.” I didn’t take any joy in seeing him in that situation. It wasn’t great for anyone. No one should have to go through this.

I’m not saying that Peter or Terry Bollea should have done this. What we have to do is understand how they felt and why they did what they did. The idea that a billionaire doesn’t feel bad when someone outs him because he’s a billionaire is a preposterously naive thing to say. In a way, it’s probably more pronounced because he thinks, “I have all this and I still feel shitty. Why do I feel shitty? What’s the point of all this wealth if I can’t use it to fix what I’m feeling?”

One of the parallels that I make in the book is that because Gawker writers were working from behind a computer screen and because they weren’t motivated by hate, that it wasn’t hurtful to people—that it was all a game. A.J. said at one point that it was “professional wrestling.” I think that’s how they justified it to themselves. And Peter, playing the villain, getting caught up in this idea of a conspiracy, which makes you feel like you’re in a movie—there’s an element of play in what he’s doing. I think that’s how Peter was ultimately able to feel that he wasn’t hurting Nick or A.J. or putting people out of work. I think there was this element of “this is a video game” on all sides.

One of the many non-video game consequences of the trial has been the fear that doing the kind of adversarial journalism that Gawker did could get you sued out of existence.

Aristotle talks about the golden mean. There’s cowardice on one end and recklessness on one end. Bravery is somewhere in the middle. Gawker’s approach to adversarial journalism was probably closer to recklessness than it was to well-sourced, cross your t’s and dot your i’s, everything is lined up, we’re bulletproof journalism. They would occasionally get things massively right—things that other people wouldn’t touch. But when they run a story about Louis CK five or six years ago and no one takes it seriously and it has no impact on his career—the reason is that Gawker ran stories about people like that all the time and a lot of times they turned out to be totally without merit. The fact that some of these things would be validated doesn’t change the fact that Gawker was right but often for the wrong reasons. If you’re going to be adversarial and throw your weight around, you better make sure you’re not massively vulnerable yourself.

Do the stakes ever concern you? Do you worry about how Gawker posting a video of Hulk Hogan compares to a billionaire deciding to bankrupt a media outlet?

I figured out pretty early writing the book that if you picked an answer you were going to upset a large percentage of people one way or the other. I tried to leave it as this hanging question. I think it’s a question we’re going to have to come together and figure out.

One thing that fascinates me is the internet’s fascination with Elon Musk. It sort of mirrors my parents’ generation’s adoration of Warren Buffett. The guys are fucking sharks! These guys are apex predators amongst the apex predators and no one gets there being nice. The whole point of capitalism is that it’s nasty and brutal and there’s pain in it but what you get in exchange for this Faustian bargain is an iPhone and growth and increased life expectancy. You don’t become Elon Musk if you don’t have to win all the time and you don’t exert your will. That’s why they all love Ayn Rand! They read that differently than most journalists do.