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

by Ryan Holiday

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.

the role of Cassandra

From: A. J. Daulerio Sent: Wednesday, June 3, 2015 To: Lacey, John, Tommy, Tom Seriously, you guys, take control over this situation. Think about the fact that you now have a fucking PR squad trying to place this story. You’re telling me you don’t have someone on your staff of geniuses who can do a better job talking about this than Ben Wallace??? I mean, FUCK Ben Wallace and then FUCK him again. Your editorial operation has spent two fucking weeks worth of radical transparency devoted to whether or not your staff should unionize but, Christ, the whole company is facing a $100 million lawsuit that could render all that “dick-twirling” pretty irrelevant. (And shit’s gonna change, when that verdict comes down. That truth is well established.) I absolutely have no personal stake in this lawsuit whatsoever. NONE. You guys, however, do. And the guy you need the most to care about it is being a real fucking pussy at the expense of your operation. This shit is happening in less than a month. Internally, you’re underprepared. And most of you know that. Stop having fucking meetings and take charge. Love you all. Fix it.

This kind of purity is childish, the domain of people who live in the realm of theory and words and recoil from the real world where someone can punch you in the face if you say the wrong words to the wrong person. There is always a defense necessary; discretion is the responsibility of freedom, the obligation that comes along with rights. If not in court, then in life. If not to other people, then to yourself. But that’s only part of it—Nick was the leader. He had allowed that to happen. He had allowed them to proceed closer and closer to trial without really bothering to think through these hard issues, without facing the hard truths about his company. Even the hard truths about how other people would see his company.

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.

“Yes. Yes. Lick ’em tomorrow, though.” And this is precisely what happens. Napoleon, too, describes warfare in that simple way: Two armies are hurled at each other and both are thrown into confusion and disarray by the force of the collision. Victory is simple. It goes to whoever reassembles and redoubles first. If either party thinks this would be a chance to rest, they are wrong. All are scrambling now—Gawker, Thiel, Hogan—not to try to get an advantage but for their very survival. They have collided with great force and are thrown into disarray. Publicly reviled, any could be down for the count. Is it stubbornness that keeps them going? Foolhardiness? Determination? Boldness? A death wish? What remains is simple: who will get to their feet fastest, confidently tell themselves “Lick ’em tomorrow” . . . and mean it?

Another maxim from Napoleon: “Never interrupt an enemy making a mistake.”

Thiel later speculated that perhaps it wasn’t that Denton didn’t want to win badly, it was that he actually wanted to lose. Perhaps he had begun to see, the way we all occasionally do when we glance at the rush of oncoming traffic or peer over a high ledge, the sweet possibility of release.

“The terrible thing about people like you is that decent people have to become so much like you in order to stop you—in order to survive.”

voir dire

“Gentlemen, you will permit me to put on my spectacles, for I have not only grown gray but almost blind in the service of my country.” His display saps the men of their anger—this man, their leader, he has suffered, too. He has been worn down by the same service that they are demanding compensation for and he has not offered a single complaint. As Washington expresses his confidence in Congress and makes his case, the conspiracy collapses with each word. It had been perfectly timed, the sympathies perfectly played, and a solution is quickly worked out. The Newburgh Conspiracy, as it would later come to be known, the one that could have killed the country before it really began, is dispatched to nothing more than a footnote in history.

The bet paid off. In Gatsby, Carraway had been in awe of Wolfsheim. “How did he happen to do that?” he asks of the 1919 World Series plot. Gatsby answers: “He just saw the opportunity.” Thiel had seen the opportunity where no one else had. He had taken it. Legally. And he had won. He had proven that “nothing you can do about it” is just what people who don’t want to do anything about it like to say to make themselves feel better about their inaction.

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). Clausewitz warned generals about the “culminating point of victory.” A point where, if blindly ridden past, flush with the momentum of winning and strength, you imperil everything you have achieved. The decision to attack one additional city, to charge after the enemy who has retreated, or to extend the battle for one more day might not just be subject to diminishing returns, it might snatch defeat from the jaws of victory. Every conspiracy runs this risk, and often, the conspirators know they have passed it only after it is too late.

Occam’s razor

But like so many conspirators, they seem not to have stopped to ask, Okay, then what?

“Be careful who your enemies are, because you will become just like them.”

mercurial,

But to be too firm, too unyielding, is to prolong the conflict or worsen it. Franklin Roosevelt had universally angered almost every one of the Allied generals at Casablanca when he told the media that he would accept only one outcome from the Germans: Unconditional Surrender. He hadn’t been thinking of policy, the words had just popped out in a press conference, but he could not take them back. The people who actually had to do the cleaning up, who needed to fight the war to a close, knew that this kind of language would only make the job harder. It had deprived Germany of a way to end the war earlier, it had united a collapsing enemy in desperation. Without a way out, tensions only increase and combatants have no choice but to fight on. Scipio Africanus, the general who defeated Hannibal, would say that an army should not only leave a road for their enemy to retreat by, they should pave it. The Romans had a name for this road, the Gallic Way.

spolia opima

There is a moment at the end of the Roman Civil War when Pompey is defeated by Caesar’s armies. Pompey, formerly Pompey the Great, finds himself simply walking away from the battlefield at the end of it. Nowhere to go, no country left, unnoticed even by the soldiers around him, having lost a lifetime of power in a single afternoon. So, too, on November 2, 2016, Nick Denton would post on his blog that the saga was over, that he had settled, and that he was simply fading back into civilian life. A hard peace, he would call it. A surrender.

The historian E. P. Thompson said that history never happens as the actors suspect, that history is instead the “record of unintended consequences.”

Champerty—the funding of lawsuits you have no direct interest in—dates back to at least medieval times. Persistence hunting, attrition, these are concepts that go back to man’s earliest days.

One of the worst things that can ever happen to a leader is to unconsciously associate resistance and criticism with opportunity. When everyone tells you you’re wrong and you turn out to be right, you learn a dangerous lesson: Never listen to warnings. And

As for Denton, what would he learn? What would he take away from it all? It would happen that he would turn to Stoic philosophy, detox from his media obsession, return to Europe, and in many ways become a better person. The joke about Denton had been that he was becoming happier, becoming human, but it really was true. It would be absurd to say he was grateful for what happened. No one enjoys seeing his life’s work undone. But there was an element of relief to it. He had come to understand what the Stoics meant by amor fati—loving, embracing the good in what has happened. A.J., too, was given a kind of fresh start. He left Gawker in 2012 but had never really been able to leave it, for the lawsuit had tied him to his former employer, keeping him in a state of arrested development.

The Streisand Effect

Arthur C. Clarke’s The City and the Stars: “There is a special sadness in achievement, in the knowledge that a longdesired goal has been attained at last, and that life must now be shaped towards new ends.”

I stood a few paces behind and felt myself recalling the line from Hamlet: He was a man, take him for all in all, I shall not look upon his like again.

These events, or at least the traits which spurred them, need not be so rare. The line from the Obamas was “When they go low, we go high.” It’s a dignified and impressive mantra, if only because for the most part, whether you liked them or not, it’s hard to deny that they followed it. But the now cliché remark should not be taken conclusively, for it makes one dangerous omission. It forgets that from time to time in life, we might have to take someone out behind the woodshed.

Regardless of any personal opinions I might have, that was the tragic and absurd message of this book. We live in a world where only people like Peter Thiel can pull something so intentional and long-term off—and it’s not because, as Gawker has tried to make it seem, he’s rich. It’s because he’s one of the few who believes it can be done. To borrow a line from Zero to One, to believe in conspiracies is an effective truth. To dismiss anything as impossible is as well.

When it comes to conspiracies, there are good ones and terrible ones and complicated ones. As I said in the introduction, the word is neutral, the application is not.

If you want to have a different world, it is on you to make it so. It will not be easy to do it—it may even require things that you are reluctant to consider. It always has. Moreover, that is your obligation if you are called to a higher task. To do what it takes, to see it through.

The cleanest or at least the clearest lesson, illustrated in word but mostly in deed by Thiel, is in the power of secrecy, of coordination, and of pushing past those situations where “nothing can be done.” In a time when computers are replacing many basic human functions, it will eventually come to be that audaciousness, vision, courage, creativity, a sense of justice—these will be the only tasks left to us. A computer can’t practice secrecy or misdirection, a computer can’t feel an urge to remake the world. Only humans can be that crazy. What you will do with this lesson, what ends you will put it to, are up to you. All I can say is that it is in these times of flux and upheaval that we may need that ambition most.