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

by Ryan Holiday

Alexandre Dumas once wrote that the king of the press has a throne everywhere. As Gawker’s page views went from thousands to millions and then to billions annually, as the rest of the media rushed to court his favor (or avoid his disfavor) and copy Denton’s business model, he began to accumulate both real power and perceived power.

“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 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.

“Because the internet has made it easier for all of us to be shameless voyeurs and deviants, we love to watch famous people have sex,”

there is a certain irony in the fact that the blinking camera sitting across from Denton in that deposition room was recording a video as well, and that what was captured on this recording would be wrenched from context and used against him in a public forum, too.

The 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

“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. You would never end up getting to the trial. You’d never end up facing Gawker down in front of a jury. The Hogan case was the one that, through 2014, Gawker, lulled and distracted by everything that was happening to it, had half forgotten about and convinced itself was an open and shut matter. The Gawker team believed the law was on their side and that they were still winning in the court of public opinion. “Do we have enough here? Or not?” Peter would eventually ask. And they did. It was time to begin the windup for the knockout punch.

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.

Over time, punching up turns into punching, period—at everyone and everything. Gawker’s growth would make it precisely what it criticized: powerful, unaccountable, unaware.

Culture eats strategy.

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.

“There are worse things than being disliked,” the novelist Walker Percy once wrote, “it keeps one alive and alert.”

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 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.

Was the founding of America not a kind of conspiracy? (“We must, indeed, all hang together, or, most assuredly, we shall all hang separately.”) Did Lincoln not conspire to pass the Thirteenth Amendment, knowing it was his only chance, that it was the only way? Was America’s entry into the Second World War not a conspiracy between FDR and Churchill? Was it not a conspiracy that took down Nixon, an unstable tyrant whose use of the hidden hand was too heavy to bear? Wasn’t there a conspiracy, led by several obscure colonels and captains in the late seventies and eighties, that rebelled against the bloat and the bureaucracy in the Pentagon, reformed military procurement, and created the F-16 and F-18 fighters? Wasn’t it a conspiracy to challenge gay marriage in the courts that brought into being what legislation had been unable to accomplish, just as it was a noble but unsuccessful conspiracy involving a mixed-race man named Homer Plessy that challenged segregation? Didn’t Branch Rickey and Jackie Robinson conspire to integrate baseball—against the objections of many, both black and white? Are we not to hope that Elon Musk’s public advocacy for sending a man to Mars is dwarfed by the secret plans, the backroom deals and complicated steps that will actually get us there? Sure, Roosevelt also conspired to stack the Supreme Court.

Nick would tell me, in one of our almost weekly chats that I had come to enjoy so much, that the lesson he had learned was that free speech was not necessarily noble by itself, that it needed to be paired with compassion and understanding.

“one person’s liberation can become another’s oppression,”