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

by Ryan Holiday

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.

Machiavelli said that conspiracies were weapons of the people. Only princes could afford to send an army against another army, he observed, but a conspiracy is available to every man.

Girard’s theory of mimetic desire holds that people have no idea what they want, or what they value, so they are drawn to what other people want. They want what other people have. They covet.

Except he was right and the words he spoke were the type a man like Thiel could not resist. “Peter, if everyone thought that way, what would the world look like?”

“I have been charged to take down a major media outlet by a group of wealthy individuals who will fund causes of action.

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,”

been? It’s a brute-force tactic that ignores the strategic value of exploiting your opponent’s fundamental weakness—if one could be found.

“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.”

Machiavelli’s warning once again rings prophetic: “Anyone who is threatened and is forced by necessity either to act or to suffer becomes a very dangerous man to the prince.”

Gawker claimed that it was ready, too, and had been for a long time. A Valleywag editor had, in 2006, complained in an interview that for all the traffic he’d snagged and media attention they’d gotten, what was really missing was a legitimate legal challenge. “We haven’t gotten a serious legal threat so far,” he said. “We’re still waiting for a good solid cease-and-desist and a good lawsuit.” They fired him for saying it . . . but they rehired him a few months later.

“Until my client is bankrupt or until you guys give up.” This could so easily be something that one lawyer says to leverage a settlement from an opponent. In fact, it is what lawyers often say to get settlements. They claim their client is going to fight to the end, but rarely is this true.

Deterrence is an important strategy. The more intimidating you are, the less people conspire against you. Yet the powerful must always be very careful with their threats, with their demonstrations of superior resources. Aimed poorly, they have a nasty habit of backfiring.

They had taken the time to think not just about what the Gawker people thought, but about what the Gawker people thought about what other people thought about them.

Today, we have a complex relationship with secrecy insomuch as we live in a world that no longer values it. Transparency carries now in the modern mind the weight of moral imperative. This two-handed truism sits at the foundation of Gawker’s mission and cult-heroism: the full exposure of open (and closed) secrets. It has become a perversion of Nixon’s line about the cover-up being worse than the crime where today it’s automatically a sin if you keep it a secret. Thiel’s plot against Gawker was wrong, it would be argued, and the obvious proof of this was that he tried to hide what he was doing for so long. Nick Denton would call Thiel a hypocrite for not meeting him in the open. “Wouldn’t the libertarian solution,” he told me, “have been to make his own counterargument? To meet speech with speech. It’s not like Thiel was lacking in outlets, or the money to make new outlets if he felt his voice was not loud enough.” It might be the libertarian way, but it certainly wouldn’t have been any kind of solution. What would Gawker have done had Peter Thiel taken it on in a war of words instead of secretly plotting its undoing? It would have torn him apart. When people who don’t like what you’re doing know that you’re trying to do it, they are more likely to be able to stop you. It’s that simple.

Imagine if halfway through the plot, Nick Denton had discovered that Peter Thiel had been scheming to destroy his company. Not only is this itself a juicy story that would have exploded as it was published and burnished Gawker’s outsized reputation, but it would also reveal Thiel’s sensitivity. That he had tried and failed to secretly settle his score against Gawker would have been a perennial taunt, and Thiel would have looked stupid for getting caught (to be outed as gay was upsetting, but to be shown as bumbling?).

Harder will repeatedly complain in arguments that Gawker has “exponentially greater financial resources than Mr. Bollea,”

What he could never do would be to say the truth: We are assembling a legal dossier. We have unlimited resources. We are pursuing as many cases against you as we can. We won’t stop until this is over, until you’re gone.

Harder himself, based in Los Angeles, is in part chosen for the purpose of misdirection. Hiring a law firm in San Francisco might have hinted at the conspiracy’s connection to Silicon Valley.

Thiel hired Mr. A as his operative for similar reasons. He is young, he is foreign, he has no footprint to speak of, there is no discernible connection between him and Peter.

Metellus Pius, leading the Roman army in Spain, is asked by one of his soldiers, “Where are we going tomorrow?” He replies, “If my tunic could tell, I would burn it.”

They wanted to hear his complaints, that he was hurting from it. They were so overconfident, so sure that this suit would come to nothing that they could not even conceive of a scenario in which Harder might have an advantage over them, or might be doing something other than being stupid.

The enemy is stagnation, and the vested interests that ensure stagnation. (And yes, sometimes also the culture of internet criticism that stymies original thought.)

And in this insane new one there was a new sense of doubt inside Gawker: Are we not bulletproof anymore?

Really it was a war on a half dozen fronts, from Dunham to interns to angry nerds online, though Nick might not see that even now.

This is what made the Hogan sex tape such an ideal vehicle for attack. It was not a typical, head-on First Amendment challenge like most media outlets are used to. “This was not a libel thing, this was Fourth Amendment privacy,”

“At some point the word ‘strategy’ becomes a euphemism for procrastination.

His husband is friendly, spiritual, empathetic, an artist from Houston, not New York. It becomes almost a running joke among his friends, Nick is happy. His heart has grown and it’s changed him. Among his employees, this is almost taken as a sign that something is wrong with him. It’s made him soft. That tinge of nihilism has been passed on to the organization like a baton of dissatisfaction.

From: A. J. Daulerio Sent: Wednesday, June 3, 2015 To: Lacey, John, Tommy, Tom Seriously, you guys, take control over this situation. Think about the fact that you now have a fucking PR squad trying to place this story. You’re telling me you don’t have someone on your staff of geniuses who can do a better job talking about this than Ben Wallace??? I mean, FUCK Ben Wallace and then FUCK him again. Your editorial operation has spent two fucking weeks worth of radical transparency devoted to whether or not your staff should unionize but, Christ, the whole company is facing a $100 million lawsuit that could render all that “dick-twirling” pretty irrelevant. (And shit’s gonna change, when that verdict comes down. That truth is well established.) I absolutely have no personal stake in this lawsuit whatsoever. NONE. You guys, however, do. And the guy you need the most to care about it is being a real fucking pussy at the expense of your operation. This shit is happening in less than a month. Internally, you’re underprepared. And most of you know that. Stop having fucking meetings and take charge. Love you all. Fix it.

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 would have put Gawker in a position to be the good guys again in front of a jury: We said we were sorry. This guy who screwed his friend’s wife just won’t let it go. But to apologize they would have had to see themselves from another perspective, an unbiased and human one that was capable of wrongdoing and meanness, and they couldn’t. Instead, their intransigence only serves to bind Hogan and Harder and Thiel closer together. These people will never be held accountable unless we do it. These people think they are above any wrongdoing.

People had been disappointed in the sex tape, but here—here they were disgusted.

At some point, the other side gets tired of being hit and lacks the energy to keep hitting back. This is what its highly paid legal advisers had been telling them and were telling them now.

They needed him to be that. And for a while it had worked, well enough that in 2015, Mr. A had begun to seriously consider hiring his own public relations team to fight back in the war of words. But Thiel had resisted. Let them talk themselves into a stupor, he thought, let them convince the troops that this is in the bag. Let them make us look stupid, let them think they are winning. Let them use all that oxygen for bluster that they are going to need if they want to gather themselves enough to confidently say, “Lick ’em tomorrow!” Another maxim from Napoleon: “Never interrupt an enemy making a mistake.”

It is with a kind of nasty glee, more characteristic of Gawker than anyone else, that Thiel’s team would recount to me, several times, a discovery which they would exploit, which very well might have been the deciding factor in the entire case. In those expensive mock juries, they had discovered that their case played exceedingly well to a very specific type of person. “It became very clear that the kind of jurors we wanted were overweight women. Most people can’t empathize with a sex tape, but overweight women are sensitive about their bodies and feel like they have been bullied on the internet.

It would be like the scene in Sweet Smell of Success where the baby-faced challenger stands up to the terrible and powerful gossip columnist who treats people like playthings: “The terrible thing about people like you is that decent people have to become so much like you in order to stop you—in order to survive.”

There was a cultivated and deliberate sense around Lyndon Johnson, an aide once said of the pragmatic, ruthless man. “There was a feeling—if you did everything, you would win.” Whatever it took. Whatever was necessary. Even if it wasn’t necessary but it might help. That’s what you did and that’s how you would stay on top. This is very different from the sense that Hillary Clinton had that she should win. Or the sense around Al Gore that he probably did win. What matters is who does what needs to be done to finish.

The call was Hogan’s. Is the tall, thin, blue-eyed lawyer who just moved his firm to Rodeo Drive in Beverly Hills really any better equipped to relate to a Florida jury than the Oxford-educated Nick Denton or Gawker Media’s D.C.-based representation? No, he isn’t, and Hogan has suggested as tactfully as he can that it’d be better if he sits this one out. Their local counsel, he says, should address the court.

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.” So on the day of the trial, Harder sits in an overstuffed leather chair behind Hogan and watches another man give the arguments he was supposed to give.

“If you want to win, ‘ego is the enemy,’” Peter would say, “and the anti-ego thing we did was downgrade Harder’s role in the trial.

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.” Thiel the nonpracticing attorney grasped this instinctively in a way that the professional lawyers for the defense clearly missed. Facts are stubborn things, and no amount of legal maneuvering could blunt them fully, not in court anyway. The person who wins the jury is the one who tells the most compelling story. Whoever is most human and personable wins. The fact of what Gawker did—running that tape that Hogan was believably claiming he never wanted to be public—was ever present in the courtroom. Who they did it to was real and indisputable, too. Gawker’s strategy was to insist that it was allowed to do what it did, and leave the implication to hang there.

He grabs his fingers nervously. He introduces himself: “My name is Terry Gene Bollea, born in Augusta, Georgia, August 11, 1953.” He has one job on the stand. To be human. To sell his lowest, lowest point, and to survive cross-examination. He does both. Gawker’s attorneys wince as they feel its effectiveness.

Ostensibly it is a chance to anticipate the hard cross-examination coming forthwith, to humanize his client before he is attacked, but it isn’t taken. Sullivan’s difficulty connecting with the jury becomes clear. Even in his questioning, he comes off as lecturing when he doesn’t mean to, punctuating every sentence with an obnoxious “Okay?” and “Do you remember that?” The jury has drifted, they are not buying what has been sold. That boredom is about to be banished. After an hour and a half of slow questioning by the defense, Shane Vogt is let off his leash and set upon his target. The full brunt of years of denied accountability, of bad legal strategy, of growing, building resentment against the media is going to pour down upon Daulerio. This will not be easy. “If I understood your testimony a moment ago,” Vogt says, hardly taking even a moment to flip through his papers, he is ready to set a new pace, an aggressor’s pace, “when you referenced your standard of newsworthiness of any child celebrity over the age of four, you were joking? Is that what you just said?” “I did say that, yes.” “You think that’s a funny topic to joke about, child pornography?” “No, not at all.” “At the time you made that joke, you were in a deposition, right?” “Yeah.” “You were in a deposition and you were asked a question about one of the central issues in this case, were you not? Newsworthiness, that’s your defense, is it not? And when you were asked a question about newsworthiness you made a jo...

A.J.’s lawyers can’t be blamed for his answers. They can’t be blamed for what he did, even if he had come to regret it. Their job is to defend speech and their clients have not made that easy. Gawker’s lawyers can’t control what he said in those private conversations, and they don’t get to choose what evidence makes up a case. Bad client, bad attitude, bad timing. Still, they do choose how their evidence is delivered at trial and how their clients are prepared. This is what they have been paid millions of dollars for. It is their responsibility. A.J.’s tone is flippant; even his body language suggests a kind of reluctance and contempt for the proceedings. As he leans his neck forward to answer each time, he seems like the teenager who just cannot seem to see that he did something wrong. The kind of teenager you want to send a message to, the one you think you need to smack for his own good. How did they let that happen? Shouldn’t their strategy have taken these liabilities into account? Isn’t this what witness preparation is for?

The great sin for a leader, Frederick the Great once observed, was not in being defeated but in being surprised. How did Denton not see this? How did Gawker’s chief strategy officer not see that this was a fight they could not win? Where was their publicist? Heather Dietrick, the one they had chosen to sit in the courtroom for them, who had been privy to every part of this case from the beginning—where had she been? Denton would say in retrospect that Gawker’s “audience share in Williamsburg was not decisive.” It didn’t matter what his friends in Manhattan or his readers in Brooklyn thought of the trial, what mattered was what the jurors thought.

Instead, they insisted on the right to be evil,” Thiel explained. The word “sociopathic” has been used on occasion to describe Gawker, but even sociopaths are generally better at judging situations, at reading people, at extrapolating how things are likely to go, than anyone associated with the Gawker team seemed to be in this moment.

This trial was an exercise in stupidity. A smart person would have seen that even an insincere apology would have made all the difference.

Nick can feel repugnance to that now. He could feel the jury questioning: Who are these people? What planet do they come from? He could see that his message wasn’t landing, that they didn’t care about free speech or transparency, not like he did. They didn’t understand him or the importance of what he did—nobody cared that the rumors Gawker posted often did become tomorrow’s news. He could look at them and feel angry at their hypocrisy, knowing that each one of the jurors in that box had probably clicked on or shared one of the types of stories they were demanding he explain.

It is a lecture and not a call to action, but he can sense this in their reactions; perhaps he sensed it even when he was writing the words. Because his next line all but apologizes for the way Gawker has made its uninspired case. “Shortly,” he concludes, “we will come to the point where the voices of the attorneys will finally be still.”

One juror wants to know if community service is an option. Wouldn’t that have been nice? If there was some way out for everyone involved that didn’t mean the financial death penalty for a group of journalists? It was, as Hemingway once put it, pretty to think so, but sadly no more than that. “I think,” the judge says with a sigh, “it’s not that type of case.” It will not be that kind of verdict, either.

The conspirators would not wait long for an answer. Six hours. Less than an hour for each year Thiel has been plotting and scheming. Barely enough time to drive back to their hotels, to collapse onto the sofa and consider what has happened over the last two weeks and what rests on the decision of these ordinary people.