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

by Ryan Holiday

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.

“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 ...

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.

Failure doesn’t put him back at square one—it costs him his private life forever.

There is no such thing as an “almost secret” conspiracy of any significance.

Having his name associated with any of it makes what was intended to be justice look like the settling of a petty personal score.

Secrecy is not just the best option, it’s the only one.

And because of its value, it was by extension dif...

There were many moments in World War II when it looked like Hitler’s unshakable faith in Enigma would finally and correctly be shaken.

Each time, the Allies must do what they can to keep the ruse alive, to keep the secret safe.

How many ships do we allow th...

sink? How many can we save? What kind of defense can we give the city of Coventry, knowing a terrible bombing is coming? What are we willing to s...

leaning over the semantic edge, as he is obligated to do on behalf of his client and in pursuit of this strategy.

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 u...

But a conspiracy is more than just an unusual opinion.

Thiel’s strategy inherently depends on secrecy.

The various coconspirators see only what Peter al...

It is also a distance separating those who know from those who don’t, creating contempt and distrust on both sides.

The troops can’t and shouldn’t know everything the general is doing, which means

the general stands alone and su...

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.

when someone pointed out that a plan like the one he outlined might backfire, the strategist confidently replied, “Nobody would know it was us.”

Except, of course, for the people he had just told.

“Psychologically, there is this weird thing where you want to brag about these things tha...

Even benign conspiracies are revealed this way, through the irresistibility of telling someone, anyone.

The

author J. K. Rowling’s pseudonym “Robert Galbraith”—which she conceived of with her publisher and attorney so she might write other fare without the weight of Harry Potter expectations sinking the chances of its success—was revealed when her lawyer told ...

Gawker’s lawyers had sized up their opponent and believed they had an advantage.

They were relentlessly exploiting that perceived advantage with each filing, each motion, each appeal and tactic that prolonged the litigation.

Harder would play into this perception, repeate...

“The truest way to be deceived is to think oneself more knowing than others”

Secrets are how real work is done.

Peter makes no secret about that. There’s an entire chapter in his book Zero to One called “Secrets.”

He’s transparent about the fact that he keeps them and believes in them. He just won’...

He never pretended to be anything other th...

“Anyone who has a guilty conscience can easily be led to believe that people are talking about him,”

Two years in, not only did Gawker not know who was behind the Hogan suit, they hardly even knew anything was happening to them.

So, too, is Gawker beginning to feel the cumulative drag of all the fights it is in, or has been tricked into. Denton has the power to stop them, but he can’t quite do it. None of them on its own seems that drastic anyway.

Gawker was being separated from its media counterparts, made to seem different, flawed, repugnant—but slowly enough that it couldn’t tell the degree to which it was happening.

Methodically, Thiel was trying to strip Gawker of its allies, and with the fog settling in thick and heavy around them, they didn’t even know it was happening.

“Keep your object always in mind, while adapting your plan to circumstances.”

Harder, seeing that Gawker and its insurance carrier were in dispute, sees an opportunity.

While it seemed odd to Gawker at the time that Hogan would voluntarily give up one of his claims and willingly eliminate the potential liability of a deep-pocketed insurance company in future settlement talks,

it was in fact a brilliant and ruthless move. Now Gawker was on the hook by themselves.

Pressure. Pressure. Remorseless pressure.

Aren’t these the kinds of tactics that the conspirators had initially avoided—because they weren’t decisive, because they weren’t exactly ethical? Yes.