Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue

by Ryan Holiday

He never had to personally sign off on any drone strikes or SEAL Team Six raids at Palantir, even if the data his company handed off made them possible. All the nasty stuff was far from view. The start-up CEO can tell himself that he is a good guy, because from his vantage point he is. We’re out here inventing things, or funding people who are. So there might be consequences that ripple through society.

But as 2012 dragged on, and as anyone attempting to engage in an ambitious conspiracy eventually finds out, at some point one passes the point of theory and enters the realm of hard reality.

Thiel could not tell himself that he was inventing something here, that this was another Silicon Valley experiment, because it was in fact something very real and altogether different from what he had ever done before. As the head of a tiny conspiracy aimed at a single individual and his company, there was no way for Thiel to push any decisions onto other people, either. Nothing could be subject to a vote. This wasn’t idle chatter over dinner with a sympathetic young person about how one might take down a media outlet if one was so inclined.

would become increasingly impossible to escape the fact that success as Thiel defined it would involve the destruction of a company that employed many people, people with families, people with no direct involvement in the article about him or similar articles about anyone else. Owen Thomas had left Gawker long ago, and sure, Nick Denton was still there, but there was no going after his business without catching Gawker’s accountant and janitor and back-end web developers in the crossfire. To paraphrase Hans Oster, Thiel would have to be the one to throw the bomb that liberated the conspiracy of its scruples and let the consequences unfold. Could he do it?

Take two steps forward. Take one step back. There is often very little visible forward momentum in a conspiracy. It is, rather, as the poet Lucretius described life, “one long struggle in the dark.”

“If you think of what you’re doing too probabilistically where you have all these different steps, and there’s a chance that all these steps fail, then the conspiracy is very complicated, like a Rube Goldberg contraption, where something is just going to break down for one reason or another,” Peter explains. “What Mr. A convinced me of in 2011 was that this is not a statistical concatenation of probabilities—it was that if we simply executed on a few of these things correctly you would win.”

So for all the setbacks, there was actually a sense of progress, momentum even. As long as those few big things were still aligned correctly, all was not yet lost. With this criterion, the situation was not quite as bad as it looked: The conspirators were battling it out with Gawker in public and yet Gawker had no idea that there was a conspiracy. They had gotten a case to stick in state court, and they were about to begin the discovery phase of the trial, a place Gawker had never been taken to before. Yes, it had not occurred exactly as expected, but that’s how it goes. “You take two steps forward and one backwards but as long as you’re progressing that’s what matters,” said Mr. A.

The great Sun Tzu said that you must know your enemy as well as yourself. To not know yourself is dangerous, but to not know your enemy is reckless or worse. Because without this knowledge, you are unaware of the opportunities your enemy is presenting to you, and worse, you are ignorant of the opportunities you present to those who wish to do you harm.

Lawrence Freedman had said in his defining work Strategy that combining with others was an important strategic move, and so it was for the conspirators early on. The other side of his sentence is that “for the same reason, preventing others from doing the same can be as valuable.” Methodically, Thiel was trying to strip Gawker of its allies, and with the fog settling in thick and heavy around them, they didn’t even know it was happening.

The Gawker group may have had a vague sense that they had enemies, sure. They knew in 2014, for instance, that Gamergate’s specific goal was to put them out of business. But they are not able to connect the dots, and it’s unlikely that Gamergate could by itself succeed in anything remotely close to that goal. They are responding, responding, responding to each individual attack, but are unable to see the strings running between them. The bad boxer rushes to defend against one punch and opens himself up to another. And another, and another.

The enemy is weaker when plunged into what the statesman Demosthenes described as a “welter of confusion and folly.” A single attack allows resistance to be concentrated, but two or three or four put the enemy between the horns of a dilemma, choosing between equally subpar options. Or, blindly hoping to avoid one attack, he falls headfirst into the other without even knowing. Nero poisoned a suspicious, paranoid rival not by putting poison in his food, because each dish was tested by an attendant. Instead, he arranged for the man to be served a harmless but very hot bowl of soup. It was in the cold water, requested and poured in by the man himself, that deadly poison was delivered. Without this suppressive cover, the countermove is too obvious: when you know where the enemy is going, you go there and block them.

“Take a line of operation which offers alternative objectives.” “Ensure that both plans and dispositions are flexible—adaptable to circumstances.” “Do not throw your weight into a stroke whilst your opponent is on guard—whilst he is well placed to parry or evade it.” Liddell Hart would compare a strategic plan to a tree, saying that a healthy one has multiple branches, and that a plan with a single branch is but a barren pole. A tree with a single branch is not a tree at all, it’s a gallows.

“At some point the word ‘strategy’ becomes a euphemism for procrastination. A lot of different plans, a lot of different plans, and they will take a long time and you never—” and there he cut himself off as he so often does. So I’ll finish it for him.

The line attributed to the management guru Peter Drucker is that culture eats strategy. It’s a truism that applies as much to conspiracies as it does to businesses. It doesn’t matter how great your plan is, it doesn’t matter who your people are, if what binds them all together is weak or toxic, so, too, will be the outcome—if you even get that far. But if the ties that bind you together are strong, if you have a sense of purpose and mission, you can withstand great trials.

Take Mr. A. In 2011, Thiel’s net worth was roughly $1.5 billion, and conservatively the interest on a billion dollars is hundreds of thousands of dollars a day. Having hooked Peter’s interest in the project, finagling himself into a role as the man on the ground, essentially anything he could have asked for would have been his, had he run back the playbook he used in Berlin. Instead of asking to be paid from the beginning—which he could have—he waits. “You prove what you can do and you get paid even more,” he says. Though he would come to draw a $25,000-a-month retainer plus expenses from Peter, it was proving himself indispensable to Peter that was the real payday. The people he would meet while orbiting Thiel’s world, the things he would learn in the course of this conspiracy, made the paycheck almost secondary. The $300,000 man is not necessarily the one who will tell you honestly, “Hey, this isn’t working. I think it’s time for you to shut this thing down and let me go.”

It always takes longer than expected, per Hofstadter’s Law, even when—and this is the critical part—one takes Hofstadter’s Law into account.

She had already won in her mind, she felt she deserved it. Trump, on the other hand, was willing to do anything, go anywhere, bear any shame, tell any lie, ally with any group if it meant he could take it from her.

It was, as Hemingway once put it, pretty to think so, but sadly no more than that. “I think,” the

Machiavelli would say that when overconfidence enters men’s hearts, “it causes them to go beyond their mark . . . to lose the opportunity of possessing a certain good by hoping to obtain a better one that is uncertain.” In plain language: perfect is the enemy of good (or good enough).

Thiel knew the importance of finishing. He had written it in Zero to One. “It is much better to be the last mover,” not the first mover. “Grandmaster José Raúl Capablanca”—Thiel’s favorite chess player—“put it well: to succeed ‘you must study the endgame before everything else.’” The conspirators had studied it, but only so far as their maneuvering took to get the other man’s king on its side. What they failed to consider was that in any chess match between masters, there is always more than one game. Each requires its own unique plan.