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

by Ryan Holiday

1919 World Series was fixed not by Wolfsheim, but with great skill and audacity by Arnold Rothstein, a Jewish gangster. A young lieutenant colonel in the U.S. Army named Dwight Eisenhower eagerly followed the game as the scores came in via telegram, and like everyone else, never suspected a thing. He would remark years later that the revelation of the conspiracy that had thrown the series produced a profound change in his perspective about the world; it taught him never to trust in first appearances.

“What important truth do very few people agree with you on?” I’ll give you mine to close this short preface: Perhaps we have too few conspiracies, not too many. Too little scheming, rather than too much. What would happen if more people took up plotting, coordinating how to eliminate what they believe are negative forces and obstacles, and tried to wield power in an attempt to change the world? We could almost always use more boldness, and less complacency. We could use less telegraphing of our intentions or ambitions and see what secrecy, patience, and planning might accomplish. We could use a little more craziness and disruption, even from the people we disagree with.

option available to many but pursued by few: intrigue. To strategize, coordinate, and sustain a concerted effort to remove someone from power, to secretly move against an enemy, to do what Machiavelli would say was one of the hardest things to do in the world: to overthrow an existing order and do something new. To engage in a conspiracy to change the world.

As Cicero said, the beginnings of all things are small, and so was this one.

At Stanford he created and published a radical conservative journal called The Stanford Review, then he wrote a book that railed against multiculturalism and “militant homosexuals” on campus, despite being both gay and foreign born. His friends thought he might become a political pundit. Instead he became a lawyer.

Thiel registered a company called Palantir with the Securities and Exchange Commission. In 2004, he would found it in earnest. The company would take antifraud technology from PayPal and apply it to intelligence gathering—fighting terrorism, predicting crime, providing military insights. It would take money from the venture capital arm of the CIA and soon take on almost every other arm of the government as clients. That same summer, just around the time that the Gawker blogs found their footing, Thiel placed a $500,000 convertible note into the hands of a twenty-one-year-old Mark Zuckerberg, becoming Facebook’s first major investor.

economist Tyler Cowen once observed that at some point in the 1970s, Americans went from being the country that took literal moonshots to being the people who waited patiently in long lines for gasoline.

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Twenty-five hundred years ago, Thucydides would say that the three strongest motives for men were “fear, honor, and self-interest.” Fear. Honor. Self-interest. All covered.

“With patience and resources,” Mr. A would come to say often on his weekly calls with Peter, “we can do almost anything.” Tolstoy had a motto for Field Marshal Mikhail Kutuzov in War and Peace—“Patience and Time.” “There is nothing stronger than those two,” he said, “. . . they will do it all.” In 1812 and in real life, Kutuzov gave Napoleon an abject lesson in the truth of that during a long Russian winter.

Eisenhower began to work behind the scenes, directing and pushing for others to limit McCarthy’s power, stripping the man of allies, using his own allies to criticize him, removing opportunities McCarthy would have liked to take advantage of. It’s because of this use of the “hidden hand” that McCarthy never knew that the president was working against him, and so when Eisenhower crushed McCarthy, and crushed him completely using the man’s weaknesses against him, it would be decades before historians could even piece the evidence together.

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point. The great strategist B. H. Liddell Hart would say that all great victories come along “the line of least resistance and the line of least expectation.” John Boyd, a fighter pilot before he was a strategist, would say that a good pilot never goes through the front door. He wins by coming through the back.

Machiavelli never said—as some might claim—that we must lose that part of ourselves altogether in the pursuit of power, he did say that for the prince who wishes to remake the world to his liking, the natural impulse to be kind, forgiving, and empathetic must temporarily be suppressed. This is not an easy thing to do, even in the face of overwhelming necessity.

do it, they wanted it to have been done, but they could not do it themselves . . . because it was unethical. Hans Oster, himself a dogged German conspirator against Hitler, would despair, “We have no one who will throw the bomb in order to liberate our generals from their scruples.” Every conspiracy is the story of

Sherman’s letter to the people of Atlanta, a city he believed must fall for his march to the sea to continue and for the North to win the Civil War. Though he’d once lived in the South, though he had not begun with any strong objection to the practice of slavery, he now saw himself as an instrument of a power that must not be slowed down. To view Atlanta, this city that lay before him and his plans, as the sum total of its people would be to make the whole affair personal, not professional, and thus impossible. “You cannot qualify war in harsher terms than I will,” he told them as he rejected their pleas to be spared. “War is cruelty, and you cannot refine it; and those who brought war into our country deserve all the curses and maledictions a people can pour out.” When someone categorizes something

“You might as well appeal against the thunder-storm as against these terrible hardships of war. They are inevitable, and the only way the people of Atlanta can hope once more to live in peace and quiet at home is to stop the war, which can only be done by admitting that it began in error and is perpetuated in pride.” And so Peter Thiel has to make himself

fool I was not to tear my heart out on the day when I resolved to avenge myself!” Ah, but what dangerous business this is. This artificial hardening is a dangerous crossroads, a bargain with our primal forces that not everyone escapes or can emerge from with clean hands. William James knew that every man is “ready to be savage in some cause.” The distinction, he said, between good people and bad people is “the choice of the cause.”

Machiavelli wrote that fortune—misfortune in fact—aims herself where “dikes and dams have not been made to contain her.” Clausewitz said that battle plans were great but ultimately subject to “friction”—delays, confusion, mistakes, and complications. What is friction? Friction is when you’re Pericles and you lay out a brilliant plan to defend Athens against Sparta and then your city is hit by the plague. Friction is when your trusted research tells you one thing but you come to find the situation on the ground is completely different, that the data had it all wrong. Friction is the Russian rasputitsa, the endless mud that makes quick work of brilliant plans and bigger armies. And so the essential trait of the successful man is not only perseverance but almost a perverse expectation of how difficult it is going to be. It is having redundancies on top of redundancies, so you can absorb the losses you eventually incur. One must not just steel one’s heart but also one’s spirit so that there is no such thing as an obstacle—just information. The earlier you spot and anticipate setbacks, the less demoralizing they will be. We want things to be easy. We want them to be clean. They rarely are. Napoleon’s dictum for the general-in-chief is that he “must not allow himself to be elated by good news or depressed by bad.” In the course of any campaign there will be plenty of both. A conspiracy meets with more setbacks than successes. It’s rolling the dice—making a decision, knowing that...

Herodotus tells in The Histories about a war between Sparta and Tegea. In it, the Spartans were “so confident of reducing the men of Tegea to slavery” that they literally brought chains with them. But they lost, having dreadfully underestimated their enemy, and with poetic justice the prisoners were “forced to wear on their own legs the chains they had brought.” Gawker’s depositions would prove not dissimilar.

Second World War hinged on one critical event: the Allied breaking of Enigma, the codes with which the Axis powers communicated their secret plans. And then the conspiracy to keep Ultra—the code name for the Allies’ codebreaking method—secret for the entire war, never letting the Germans and Japanese and Italians know that they knew their every move.

Hitler’s unshakable faith in Enigma would finally and correctly be shaken. Each time, the Allies must do what they can to keep the ruse alive, to keep the secret safe. How many ships do we allow the U-boats to sink? How many can we save? What kind of defense can we give the city of Coventry, knowing a terrible bombing is coming? What are we willing to sacrifice of ourselves to keep this edge?

to have been a straightforward case to litigate. . . . Instead, Gawker used discovery in this case as a means to exponentially increase Mr. Bollea’s fees and costs—in an effort to make the case impossible for him to litigate. Gawker also sought to further punish Mr. Bollea for having the temerity to challenge Gawker’s publication of the Sex Video in court . . . two years of needless litigation.”

“The truest way to be deceived is to think oneself more knowing than others” is La Rochefoucauld’s maxim.

Russians call this maskirovka—the art of deception and confusion. It is as old as strategy itself. Undermine your enemy, Sun Tzu advised 2,500 years ago. “Subvert him, attack his morale, strike at his economy, corrupt him. Sow internal discord among his leaders; destroy him without fighting him.” Call down the fog of war, he was telling conspirators and generals and swordsmen, let it descend on your opponent until they cannot see what is right before them. Because “all warfare,” Sun Tzu reminds us, “is based on deception.” Not just keeping secrets—that’s the first part, the passive part, a refusal to reveal your true intentions—but active, outwardly focused deceit intended to disorient and weaken the enemy.

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.

Confusum est, quidquid usque in pulverem sectum est—cut anything into tiny pieces and it all becomes a mass of confusion.

Being feared, Machiavelli says, is an important protection against a conspiracy. The ultimate protection, he says, however, is to be well liked. Not simply because people who love you are less likely to want to take you down, but because they are less likely to tolerate anyone else trying to, either. If a prince guards himself against that hatred,

ancient Rome, slaves who revealed conspiracies were often given their freedom in exchange. The conspiracy against Nero collapsed when a plotter named Scaevinus asked his servant to sharpen his dagger and hosted a generous dinner where he gave away most of his fortune. The servant took news of this strange behavior to the emperor. An insider to the Gunpowder Plot to assassinate King James I would write an anonymous letter that exposed Guy Fawkes’s involvement in 1605 and earned Fawkes a one-way trip to the gallows. François Picaud, the man who inspired the story that became The Count of Monte Cristo, found his revenge plot partly thwarted when he was betrayed by a collaborator who attempted to blackmail him. In the end, this blackmailer murders Picaud himself and relays the whole story on his own deathbed a few decades later, turning the most famous revenge plot in the history of literature into a meta-warning to every would-be conspirator today: beware your allies.

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.

get smoked.” “A wound to the reputation not only does not heal, but grows deeper every day which goes by,” E. L. Godkin wrote in Scribner’s Magazine more than 125 years ago. He wrote this about the rise of the mass newspaper, in an article that would inform Justice Brandeis’s “Right to Privacy” argument. Godkin would say there was one way to heal those wounds: a “formal and public refutation

Bullying, attacking, criticizing, all of it permissible under the limitless scope of the First Amendment. 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.

Culture transcends strategy.

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.

Hofstadter's law

Churchill once compared an offensive force to throwing a bucket of water over the floor: “It rushes forward, then soaks forward, and finally stops altogether until another bucket can be brought.”

Shiloh, Ulysses S. Grant had been caught by surprise. Flush off two victories, convinced he had superior resources and tactics, he was confident he would win. Yet he had thrown everything he had at the Confederates and been thrown back. It had begun to pour rain on the troops as they attempted to settle in for the night. Grant had seriously injured his leg in a fall a few weeks before. He is desperately short of reinforcements. Sherman finds him and begins to politely discuss plans for retreat. He says to him, “Well, Grant, we’ve had the devil’s own day, haven’t we?” Grant, backlit by the camp lantern, squints as he clamps down on the stub of his cigar, “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.

But a trial is not about a judge—who is an arbiter in matters of law. It’s about a jury—who are arbiters in matters of fact, but make decisions, like all human beings, based on emotion. Hogan knew his audience. Charles isn’t “Florida people.”

snatch victory from the jaws of defeat. George Washington had done such a thing quite simply and masterfully in New Windsor, New York, at the end of the American Revolution. The war had been won but the peace had been bungled, and angry veterans were without their pensions. They had plotted and schemed and were on the verge of overthrowing Congress. Washington had been preoccupied and let the situation sneak up behind him. Congress had been entitled and unaccountable and also had not taken this threat seriously. A meeting is called of all the officers in the army. The mood is tense. The very existence of civil authority in America hangs in the balance. Washington knows he does not have much time and surprises the men by walking into the meeting. He asks quietly for the floor, and he begins to speak to his men impassionedly, begging them not to be swayed by these wicked plans. Then, simply, he reaches into his pocket to read a letter from Congress. He moves slowly, fumbles on purpose with the letter, and says, “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 p...

The great sin for a leader, Frederick the Great once observed, was not in being defeated but in being surprised.

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.

Whom he donated money to, what causes he supported, that his doctor was an advocate for a process known as parabiosis which transfers youthful blood into patients as an antiaging treatment. Thiel’s victory over Gawker had proven Gawker prescient: that he was deserving of coverage and that people would love to hate him.

we live in a country where the media would give literally billions of dollars of free publicity to a candidate they despised and were then shocked when the man ended up being elected.

at the end of one of his favorite novels, 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.”

“The idea of a conspiracy,” Thiel would say to me, “is linked with intentionality, with planning, working towards longer-term goals. In a world where you don’t have conspiracies maybe also those things disappear.” The truth is that Gawker already believed we lived in that world. And so do far too many people.

To borrow a line from Zero to One, to believe in conspiracies is an effective truth. To dismiss anything as impossible is as well.