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

by Ryan Holiday

“Anyone who has a guilty conscience can easily be led to believe that people are talking about him,” Machiavelli warns conspirators. “A word with another meaning is overheard which shakes your courage and makes you think it was said with respect to your plans. The result is that you either reveal the conspiracy yourself by fleeing or you confuse the undertaking by acting at the wrong time.”

One of its writers, Sam Biddle, formerly of Valleywag, tweets: “Ultimately #GamerGate is reaffirming what we’ve known to be true for decades: nerds should be constantly shamed and degraded into submission,” and jokes that the solution is to “Bring Back Bullying.” It is another joke in the worst possible moment.

Lawrence Freedman had said in his defining work Strategy that combining with others was an important strategic move, and so it was for the conspirators early on.

Liddell Hart’s maxims for strategy: “Keep your object always in mind, while adapting your plan to circumstances.”

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.

In Florida, the law states that plaintiffs can’t recover damages for unintentional emotional distress in cases without physical injury.

“A good entrepreneur could deal with a couple of these things,” Mr. A would say of the position they had put Denton in, “but five or six is too much.” That is the idea. To push them beyond their capacities so they would begin to make mistakes, begin to question even their own judgment.

Being feared, Machiavelli says, is an important protection against a conspiracy. The ultimate protection, he says, however, is to be well liked. Not simply because people who love you are less likely to want to take you down, but because they are less likely to tolerate anyone else trying to, either.

Most conspiracies are not found out. They are betrayed. Or they collapse from within, a betrayal of the cause itself.

How are these men going to fight through the exhaustion that comes with attrition?

The line attributed to the management guru Peter Drucker is that culture eats strategy.

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 ha...

Its writers participated in a fraction of the value they created. Denton paid himself a $500,000 salary.

They had trouble thinking about the consequences of their actions and the optics of how they would be perceived.

what is the thing they have not planned for?

He believes the world is precarious—he’s been told of its instability too many times by people who could vividly describe losing everything.

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

Getting in front of real jurors is no easy feat in the American legal system.

The critical question then is how you respond to this setback, a setback far more serious and demoralizing than the trough of sorrow which happens earlier—for this is when you felt like you could taste victory, that it was within your grasp.

There is one upside to losing it all. What is it? At least for a conspirator, now you have nothing left to lose.

Victory is simple. It goes to whoever reassembles and redoubles first.

On that day his partners “woke up and saw for the first time that my mind had not been idle while they were talking so big and loud,” he would say later. They were shocked. They’d seen their empire dismantled and taken from them by the young man they had dismissed. Rockefeller had wanted it more.

“It’s a game of spouses, too,” Mr. A would say of conspiracies. “We think it’s about the principal figures, but if the spouses at home say we should settle, things could be over.”

“It’s going to be a marathon,” he would say to his team, “we just can’t conk out. There are all these psychological things Gawker is going to try to do to get us to not fight as hard and we can’t let them influence us. I’m not going to try to reach a compromise. I’m not going to try to talk to them.”

He spent nearly $100,000 for his lawyers to conduct not one but two mock trials in Florida.

“The polemical way to say this is that, what sort of investigative journalism outlet can’t even aggressively investigate the conspiracy directed against it?” Peter would say.

Gawker’s mission had been to say the things that other people were afraid to say, it was a site that was dedicated to the idea of showing how the world really worked, yet with its life on the line it was silent and it was blind.

The joke about Florida is that the farther north you go, the deeper South you are.

Napoleon: “Never interrupt an enemy making a mistake.”

Hope is rarely enough. Especially against an opponent who has come to be consumed by their cause, who can see and taste victory now, and will do everything they can to seal it.

“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.”

What matters is who does what needs to be done to finish.

Who wants it more? Who wants to win most badly?

“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.

The person who wins the jury is the one who tells the most compelling story. Whoever is most human and personable wins.

This would be a fatal miscalculation to make when your fate rests on the decision of six ordinary people who aren’t inclined to make a distinction between immoral and illegal,

“PR can be powerful, it can be effective, but it can always backfire when you start to believe it too much. They needed to say they were sorry. If they had done that, they would’ve survived. Instead, they insisted on the right to be evil,” Thiel explained.

All the good work that Gawker had ever done, all the real news Denton’s writers had broken, the stuff Nick was rightfully proud of, was being erased.

Machiavelli would say that a coup or a conspiracy can succeed only if the will of the people is on its side.

He had proven that “nothing you can do about it” is just what people who don’t want to do anything about it like to say to make themselves feel better about their inaction.

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.

But what would the consequences, intended and otherwise, of it all be? What had this brilliant, independent mind neglected to see? What, if anything, would come as a surprise? His own power and strength for one.

He learned another important lesson in that Florida courtroom, this one also about America—that average and ordinary people cared little for the assumptions of the so-called elites.

There may indeed be too few lawsuits in America, but there is plenty of outrage to spread around.

Peter had gone after Gawker because he believed that he was a private person and deserved a private life, but the great irony of his victory over Denton was that it had made him a celebrity—one whose every action was now, by definition, news.

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

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.

Because the end of a conspiracy can be not unlike the beginning of it: an intolerable status quo.

It would be a little more elegant if the reading public recognized their own contribution, that they get precisely the media that they click on and talk about.”

It is said that the weapons invented at the end of one war become the dominant killers in the next one.