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

by Ryan Holiday

Conspiracy entails determined, coordinated action, done in secret—always in secret—that aims to disrupt the status quo or accomplish some aim.

It’s the 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.

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.

What Denton did, in effect, was turn writing, social commentary, and journalism into a video game. Writing wasn’t a craft you mastered. It was a delivery mechanism. The people and companies you wrote about, like Peter Thiel, weren’t people, they were characters on a screen—fodder for your weekly churn. And the people you got to read this writing? They were points. The score was right there next to your byline. Views: 1,000. 10,000. 100,000. 1,000,000.

If a piece didn’t go hard enough, if there were rumors the reporter wanted to talk about but couldn’t justify even with Gawker’s thin standards, there was always the comments section to push the story from behind—or the bottom, as it were—and drum up tips and speculation and titillation that might lead to more attention.

A movie executive once described the “honeyed sting” of the notorious twentieth-century gossip Hedda Hopper as a black widow spider crossed with a scorpion, weaned on prussic acid and treacle. In a way, that was Gawker, too.

One of the early slogans for Gawker’s sports site, Deadspin, was “News Without Access, Favor, or Discretion.” To Denton that slogan wasn’t just branding. “I would own those words,” he would say later, under oath. If there was ever a statement that reflected both the man and his monster, this was it, because this wasn’t just Denton’s character, this was his editorial policy, too. A close friend would describe Denton as “completely unsentimental, contradictory, and opaque.” To some journalists, lacking access or discretion would be a weakness. In Gawker’s model, they are shackles to throw off. Without them, writers could do things that other outlets could not. They weren’t afraid to burn sources, to name names, to run stolen material, to take anonymous leaks. We don’t want to know your real name, they would tell sources, we just want the dirt.

What he knew was that most people did not have the stomach—or the cash—to actually take it very far against a media outlet. He felt protected by the moat explained in the old twentieth-century proverb: Never fight a battle against someone who buys ink by the barrel. It’s easier to just let the whole thing go.

Gawker’s forte was breaking news, and it rarely let obstacles prevent them from doing so. This mindset was responsible for Gawker’s decisions in the years that would follow to take on Steve Jobs over a stolen iPhone prototype, to publish a controversial recruiting video produced by the Church of Scientology, to (correctly) accuse the mayor of Toronto of being a crack addict. It was why Gawker was one of the first to reignite rumors of Bill Cosby’s alleged sexual assaults, and published anonymous claims about actor Kevin Spacey and young boys, as well as the misdeeds of the director James Toback and comedian Louis C.K.—stories the rest of the media would come to seem embarrassingly late on reporting.

The distinction between a conspiracy and a feud is as much in the time it takes for one to spring into action as it is in the type of action that one takes. In a fight, one responds to a punch by throwing a punch. In a conspiracy, one holds their punches and plots instead for the complete destruction of their antagonist, while often intending to escape with knuckles unbloodied and untraceable prints. Fights break out. Conspiracies brew.

Most people, when they find something they don’t like, do that. They call it names. They complain. They make it bigger than it is, make it representative of some larger trend. They think someone should do something, but never them.

For a complicated man with specific opinions about complex ideas, one might suspect that the gravest threat Gawker posed—why it seemed to him to be a form of terrorism—was the tendency for its trenchant, snarky reporting to become reductive and to cause collateral damage.

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

Barbra Streisand sues to remove a picture of her house from the internet, and not only does she lose, but more people see the photo than otherwise would. It is a behavioral phenomenon that gets dubbed, fittingly, the Streisand Effect and has stood as a warning since: the media always wins in the end.

Is this not the source of the tension between Denton and Thiel, not because they are so different, but because they are so similar?

“Anyone who is threatened and is forced by necessity either to act or to suffer,” writes Machiavelli, “becomes a very dangerous man to the prince.”

Machiavelli writes that a conspiracy without any coconspirators is not a conspiracy. It’s just a crime. This is also basic legal principle. If you kill someone by yourself, in the heat of the moment, it’s murder. If you meticulously plan it with someone else beforehand, that’s conspiracy.

By definition, the first move in the act of a conspiracy is the assemblage of allies and operators: your coconspirators. Someone to do your bidding, to work with you, someone you can trust, who agrees with you that there’s a problem, or is willing to be paid to agree with the sentiment that it’s about time someone, somebody did something about this. Each hand doesn’t need to know what the other is doing, but there needs to be more than one set.

The professional son understands what every father wants—a progeny worth his time, someone to invest in, someone who can further his legacy. The professional father wants to see his greatness given a second body—a younger one, with more energy, with the benefit of his hard-won experiences.

It would be a mistake to confuse Peter’s pondering Socratic-ness for uncertainty. His mind, for all its detours and considerations, ultimately meanders toward precision, the kind that calculates down to the ten-thousandth decimal point in ordinary conversation.

This compartmentalization is key to a conspiracy. Not everyone can be in charge. Mr. Harder works for the clients whose bills are paid by Mr. A, who works for Mr. Thiel (while Mr. Harder does not know who Mr. Thiel is). Not everyone can know every element, or give their opinion on all of it. Not every decision can be explained or needs to be. At some point, some people’s job is just to answer the phones, to press the buttons, to shred the documents, to argue in court, because that’s what they are paid to do. They are paid to do a job.

But that’s the nice thing about lawyers: as long as you’re paying them, they’re usually good with whatever terms go along with it. Compartmentalization is their job.

We are often taught that successful strategy is a matter of boldness, but it has also always been the case that it’s as much a matter of patience and due diligence as it is of noticeable action.

“With patience and resources,” Mr. A would come to say often on his weekly calls with Peter, “we can do almost anything.”

But this isn’t how Thiel thinks. He would say his favorite chess player was José Raúl Capablanca, and remind himself of the man’s famous dictum: 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.

Given the resources he had to draw on, the limitlessness of the options is nearly true: they could have bribed employees at Gawker to leak information, or hired operatives to ruin the company from the inside. They could have directed hackers to break into Gawker’s email servers. Someone could have followed Nick Denton and, while he dined at Balthazar one morning, stolen his cell phone. A team could have attempted to bug the Gawker offices. You could fund a rival website, operate it at a loss, and slowly eat away at the razor-thin margins of Gawker’s business. Or create a blog that does nothing but report on gossip about Gawker writers—returning the very pressure and

scrutiny they’d put on other people. “There are things that were very tempting, an eye for an eye, tooth for a tooth. Retributive justice,” Peter said. “But I think those would’ve ultimately been self-defeating. That’s where you just become that which you hate.” The victory would be pyrrhic, too, easier but at a higher personal cost.

A decision was made to eliminate the strategies that would either be illegal or fall into any one of a number of gray areas. For instance, Thiel could have easily hit Gawker with many meritless cases that he never expected to win in order to bury the company in legal bills, but how effective would that really have been? It’s a brute-force tactic that ignores...

“Peter is the kind of opponent you’d want,” a friend would say about Peter’s insistence on operating from principle, “except that you wouldn’t want him to have unlimited resources.”

The degree to which one succeeds or fails in this endeavor tends to determine not only how well one sleeps at night, but also how the public ultimately views who was in the right. Ethics don’t win the war, but they do help keep the peace.

It has been the great collective self-deception of Silicon Valley, and perhaps of our age, that a person can engage in aggressive “disruption” of existing industries while pretending that they are not at least similar to the ruthless capitalist barons of the previous century, that there is not a drop of Carnegie or Rockefeller or Vanderbilt DNA in the whole business. Peter Thiel didn’t have to personally fire the bank tellers that he put out of a job at PayPal. He wasn’t deliberately driving down the stocks of the newspapers in order to boost the stock of Facebook, even if that was the ultimate effect. He never had to personally sign off on any drone strikes or SEAL Team Six raids at Palantir, even if the data his company handed off made them possible. All the nasty stuff was far from view.

It’s hope that makes disappointing news so crushing.

It’s the drive where you hit every red light. The project where everything seems to go wrong, at the same time. When you ask yourself, “Why can I not just catch a fucking break?” It is the nature of conspiracy. If it was easy, everyone would do it.

So for all the setbacks, there was actually a sense of progress, momentum even. As long as those few big things were still aligned correctly, all was not yet lost.

The great Sun Tzu said that you must know your enemy as well as yourself. To not know yourself is dangerous, but to not know your enemy is reckless or worse. Because without this knowledge, you are unaware of the opportunities your enemy is presenting to you, and worse, you are ignorant of the opportunities you present to those who wish to do you harm.

Thiel had said something to Wired magazine not long before this juncture, speaking not about the case but about an investment, that makes it clear how much he relished this kind of ignorance. It’s what he exploits, counts on even. “The things that I think I’m right about,” Thiel said, “other people are in some sense not even wrong about, because they’re not thinking about them.” In this sense, it’s an oversimplification to say that Gawker was wrong about the threat it faced. It was actually much worse. It was totally and utterly unaware of it—unaware

In every conspiracy, there is temptation to talk, especially as you near your goal. The weight of silence and deceit begins to weigh on the participants. You might be sitting at a dinner with all your friends. Each speaks with such ease about their recent successes, each is able to talk freely and share their opinions. Yet you can say nothing. The conspiracy has consumed countless waking moments, produced a number of successes you want to brag about, and probably even more difficulties that you could desperately use support and reassurance on, but you don’t say a word.

There’s an old line that in war the truth is so precious that it must be protected by a bodyguard of lies.

Being feared, Machiavelli says, is an important protection against a conspiracy. The ultimate protection, he says, however, is to be well liked.

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.

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.

Most conspiracies fail and most fail from the inside, not the outside.

He is in it to the end, and now hopeful, too. Because something was made clear with that enormous offer: Gawker didn’t want to go to trial.

Yet unlike Denton, Thiel wasn’t content to simply ballpark his odds. He wanted proof that the case had the legs to go the distance. What can we know that they don’t know? Where’s our edge? He spent nearly $100,000 for his lawyers to conduct not one but two mock trials in Florida. Gather up a bunch of prospective jurors, pay them by the hour, and run the case in front of them. Judge every reaction, learn everything they like and don’t like.

I have heard Peter Thiel say over and over again that in the trial, Gawker argued the law while Hogan’s case argued the facts. “You argue the law to show how much you know about the law,” he would say, “but it’s not how you win a case in front of a jury.”

Still, they do choose how their evidence is delivered at trial and how their clients are prepared.

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

Mr. A watches it unfold live via online broadcast of the courtroom. The quiet operator is mad with glee and pleasure. He picks up his phone to call Peter Thiel. It’s the game of telephone, from the courtroom to the safe house, until it reaches the mastermind, away in China, teaching a class of university students who have no clue what their professor has been working on.

Peter Thiel has done what presidents, robber barons, and folk heroes have been unable to do. He has fought a battle with the people who buy ink by the barrel and come out the better for it.

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.