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

by Ryan Holiday

Machiavelli warns conspirators that the most dangerous time is after the deed is done.

In a wrestling match, he would say, when one wrestler begins to beat too unfairly on his opponent, they switch sides.

Cunning and resources might win the war, but it’s the stories and the myths afterward that will determine who deserved to win it.

How one rides out the chaos in the aftermath of a deed is everything.

Charlie Wilson worked with the CIA to fund a guerrilla resistance to the Soviets in Afghanistan and won. There wasn’t much of a plan for what to do with these trained and armed fighters afterward. He would say, “These things happened. They were glorious and they changed the world. And the people who deserved the credit are the ones who made the sacrifice. And then we fucked up the endgame.” Those same fighters became the Taliban and sheltered Osama bin Laden.

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.’”

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

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.

The conspirators would find that victory required a kind of defensiveness still.

The historian E. P. Thompson said that history never happens as the actors suspect, that history is instead the “record of unintended consequences.” The assassination of Julius Caesar does not restore the Roman Republic, it leads to a brutal civil war and, at the end, another emperor. The Allied powers destroy Hitler and Germany but empower Russia and Stalin and create a new Cold War to follow the conclusion of the hot one. There is always something you didn’t expect, always some second- or third-order consequence.

In Maui, where Thiel has a home and spends a good deal of his time, officials once introduced a species of mongoose to kill rats. Only after introducing them did it occur to anyone that rats are nocturnal and mongooses are diurnal. A bad problem became worse, a rat problem became a mongoose problem. You launch a conspiracy to protect your privacy and make yourself famous. You seek to rid the world of a bully and you find yourself with Trump. The nihilists on the left are sent in a diaspora from Gawker to other media outlets, matched tit for tat by the nihilists on the right. And most of them hate you.

When everyone tells you you’re wrong and you turn out to be right, you learn a dangerous lesson: Never listen to warnings.

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.