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

by Ryan Holiday

Peter Thiel had at

first despaired of a fight with Gawker because he felt a certain powerlessness, that it was a media outlet, that it had the First Amendment to hide behind and there was nothing he could do about it.

Now here, at least in this specific instance, seeing Gawker’s legal strategy laid bare, that ...

There is something about the arrogance of Nick Denton’s position that grates on Thiel, that drives him to continue almost out of spit...

The world had not stood still in the years since Gawker launched, and readers were far less inclined to look at being gay as a secret to expose, as they had been when it had been done to Peter Thiel.

It should be said that Gawker’s legal team had always and reasonably held

a basic assumption, and it’s one that undergirds the litigation system: people will act in their rational self-interest.

Except it didn’t quite go that way.

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

Gawker counted on his giving up at some point. Even his backers had to consider the contingency that he might eventually settle and leave them without a client.

It’s not even a matter of winning anymore. Both sides have spent several million dollars thus far. Both have made huge wagers on their public reputations.

Peter can’t walk away.

Gawker’s reputation is on the line.

All are scrambling now—Gawker, Thiel, Hogan—not to try to get an advantage

but for their very survival.

They have collided with great force and are throw...

Every conspiracy, every campaign, is a battle of wills.

And though we’d like to think that planning and resources—or righteousness and worthiness—determine who wins and who loses, they don’t. So often these things come down to a simple factor: Who wants it more?

Donald Trump was underprepared, erratic, constantly in his own way.

But it cannot be said that he did not want to win very badly. He wanted to win even more than Hillary.

The last few weeks of the election made that fact indisputable. She had already won in her min...

Trump, on the other hand, was willing to do anything, go anywhere, bear any shame, tell any lie, ally with any group if i...

And h...

Gawker did, however, make a number of settlement offers.

No attorney lets his or her client walk away from an eight-figure settlement, not with this much baggage weighing him down. It would practically be a breach of their fiduciary duty. This was not only a test of faith, this was a test of mettle.

Though the other offers had been legitimately made and it appeared that Hogan was tempted by them, $10 million was money of another kind. If only they knew just how close Hogan was to accepting it.

Bollea’s wife extracts a promise: if they offer you $20 million, you have to take it.

All that could end now. He would be spared the media attention and end up a very rich man again. He has no legal fees, after all. That’s been seen to. He can just walk away.

Even long after the conspiracy had ended, Gawker seemed to be unaware of what it must have taken from the conspirators to keep Hogan in the game.

Certainly many people have settled better cases for less, even people who had come to hate their opponent as much as Hogan and Harder did.

Although the number would creep upward in informal talks,

it was never going to happen.

At the end of the day, Bollea tells himself he...

the money. After they had threatened, after they had been party to the destruction of his career, there really was no number, he admit...

Gawker’s heavy persuasion from beginning to end had had the opposite effect. It only increased Hogan’s anger and hardened his resolve.

His desire to punish and to prevent is too great. Wrapping his own case up in a larger, vaguer cause of justice for everyone written about by Gawker, he couldn’t just stop.

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.

He could smell fear through the posturing. He could see it.

That hardness in Thiel, what he’d committed to earlier, never seemed to have wavered.

He could have quit when Hogan was exposed. He could have let Hogan off the hook now, let the momentum naturally peter itself out and know that he had cost Gawker more than anyone ever had. That he’d landed more blows than anyone else and that Gawker would be forever humbled and changed for it. Walking away, accepting the settlement would have also all but guaranteed the secrecy of his involvement, too, allaying the reputational fears that exposure brought with it. But the will to continue is stronger. The push for the knockout blow persists.

Yet unlike Denton, Thiel wasn’t content to simply b...

He wanted proof that the case had the legs to ...

what sort of investigative journalism outlet can’t even aggressively investigate the conspiracy directed against it?”

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 a...

All this money, all these avenues, spent and pursued in order to leave nothing to chance and to find every edge, every opportunity to land the decisive blow.

His team has been poring over case law to figure it out, to be sure they aren’t missing anything, to put themselves in a position

not just to win, but to win decisively.

Denton? He is winging it, hoping simply not to lose instea...