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

by Ryan Holiday

One that, as it spun out of control, growing bigger and bolder, even he privately began to worry might lead to a suicide. As so many reactionary organizations tend to do, it had begun to drift toward absolutism and nihilism.

Machiavelli said that a proper conspiracy moves through three distinct phases: the planning, the doing, and the aftermath. Each of these phases requires different skills—from organization to strategic thinking to recruiting, funding, aiming, secrecy, managing public relations, leadership, foresight, and ultimately, knowing when to stop. Most important, a conspiracy requires patience and fortitude, so much patience, as much as it relies on boldness or courage.

“The beginnings of all things are small,” Cicero reminds us.

Overeducated children of Boomers, the children of parents whose idealism became materialism, the writers believed they had something to say because those same parents had told them they were special and important and talented.

Never fight a battle against someone who buys ink by the barrel. It’s easier to just let the whole thing go.

The 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. It’s not completely accurate, of course, but it is a criticism that resonates with Thiel as he sits in his office at the Presidio one day looking at the Golden Gate Bridge and wonders if people will ever build something like that again. Do people even have the arrogance anymore? To test the limits? To try big things? What’s more, there is evil in

You rush in to stamp out the sparks and end up fanning them into flames. This is the risk. In

He thinks the outlaw Jesse James is a great man. He thinks that he, himself, is a great man, too. He wants someone to recognize that in him. He wants someone to give him an opportunity—a project through which he can prove his worth. It just happens that Frank James would size the delusional, awkward boy up in the woods outside Blue Cut, Missouri: “You don’t have the ingredients, son.”

To begin you must study the end. You don’t want to be the first to act, you want to be the last man standing.

Seeing that opposition and publicity were what gave McCarthy his power, he looked for a better opportunity. 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.

“Given the same amount of intelligence, timidity will do one thousand times more damage in war than audacity” is the dictum from Clausewitz.

This transition is common: one can’t see one’s choices as simply selfish or personal or one would never have the strength to do what ultimately needs to be done. In the way that it became important for Thiel to see Gawker as singularly bad, the conspirator takes up, often without consent, the mantle of defending (or freeing) a number of other people as his or her real reason for proceeding. It is a sort of self-serving selflessness, a shield against what

When someone categorizes something evil, as Sherman did, as Peter and Mr. A repeatedly did, he implicitly gives himself permission to do what needs to be done to destroy it. It cannot have been easy for Sherman

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

conspirators would do would align with the British historian Liddell Hart’s maxims for strategy: “Keep your object always in mind, while adapting your plan to circumstances.” “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.

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.

aggressively. Because we’re gonna 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 of the slander.” That is, an apology. It never occurs to anyone at Gawker how easily such a gesture would have frayed the bonds that tied its enemies together. An apology would have sapped the conspiracy of its power and put Thiel’s and Hogan’s goals in conflict. It

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.

Berry is the opposite of Shane Vogt, not relatable or confident.

The next step is holding on to the victory. No matter how brilliant you are, how impressive the conspiracy was—it will be defined by what comes after.

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.

Thiel is once again in the catbird seat, having taken the world by surprise one more time. He had proved not only that we live in a country where a person can conspire to put a publication out of business, but that 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. If one

“These people,” Thiel would lament, six months into Trump’s presidency, about the alt-right leaders he was now tainted with by association, “they are the most like Gawker. It’s not that they are willing to do anything in the name of the ideology, that’s the ends justifying the means. . . . The similarity is the nihilism: a mask for no ideology at all.”

This must hit Thiel sometimes, perhaps in the quiet cabin of his Gulfstream, that the man in the White House is essentially the opposite of everything he had spent his life believing in, that Trump threatened the very libertarian freedoms and open civil discourse that Thiel had spent his money protecting. To know he is associated with that, in certain ways responsible for it, might be the most unintended consequence of all. In Maui, where Thiel has a home

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.