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

by Ryan Holiday

but they hadn’t. Gawker bet it all on this one chance; it won’t be getting another.

There was much left to be done—many reams of paperwork left to be prepared and paid for, more lawyers to hire and hearings to attend,

but he has done it. At last he has done it.

The bet pa...

Thiel had seen the opportunity where no one else had. He had taken it. Legally. And he had won.

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.

A conspiracy is possible only with secrecy, but secrecy is subject, like all things, to the law of entropy.

For some time Thiel’s secret had been decaying, his grip on the absoluteness of it had slipped. Though he’d told very few people what he was doing, in the course of a decade, the list of names added up.

As victory approached, caution had relaxed into confidence, which was eventually ...

The decision not to simply slip away during the chaos, but instead to give away too many clues by talking about the conspiracy, would come to haunt Peter.

It would be his biggest mistake. Especially against this opponent, the one who knows what to do with suspicions and speculation.

In plain language: perfect is the enemy of good

What ultimately tipped Denton remains a mystery.

Once the what and the where had been established, confirmation of the who was only a matter of time.

For the first time, coverage of the most media-centric story of the year is no longer tinged with amusement about the lurid details of a celebrity’s private life or whether sex tapes were newsworthy, but rather with anger and rage and anxiety.

Now it was: Should people be able to do what Thiel had done? Is the entire right to a free press imperiled?

The coverage had turned and only one fact had changed, the fact about who had paid Charles Harder’s legal bills.

Even the conspirators, long in the dark, are surprised by the news.

A decade of secrecy has been undone in less than ninety-six hours.

Along with it, much of the carefully constructed narrative that Gawker was unique and evil, that it deserved this, that this was a grassroots and organic

rejection of a culture gone bad, teeter...

“It was scarcely believable that something so cinematically vindictive and conspiratorial and underhanded could have actually happened,”

Which, undoubtedly, is why it happened.

Thiel is just as unprepared for it.

“We didn’t think it was going to happen, so yes, we were caught by surprise.”

He is caught by surprise not only by the news, but by the direction t...

The revelation of Peter’s name immediately flips the narrative that many reporters and commenters had been running with.

Now all of a sudden, it wasn’t Gawker, the bully, beating up on Hulk Hogan, it was a megalomaniacal billionaire threatening free speech.

The idea that Gawker could have perhaps quite handily prevailed at trial with a better legal strategy was immediately replaced by the per...

The fact that a judge had ruled the case legitimate and a jury had found for Gawker’s opponent—all these realities of recent history disappeared.

And the hope of a clean victory went with them.

Machiavelli warns conspirators that the most dangerous time is after the deed is done. It is as if Peter and Harder did not fully consider this.

Loss inherently makes the loser sympathetic.

We can easily be

made to feel bad for the person on the other side of a true catastrophe, even if just minutes before we thou...

Thiel and Mr. A, both foreign born, had forgotten that essential quirk of the American character—the inclination t...

In a conspiracy that was so brilliantly planned and orchestrated, calculated in every way down to its probabilistic decimal point, where no expense was spared, this can’t be seen as anything but little and late.

But like so many conspirators, they seem not to have stopped to ask, Okay, then what?

What he missed was that to take down one media outlet would make him an enemy to all the others, even if they never liked Gawker to begin with.

That it would be seen as an act of retribution and would invite retribution in return.

While we may not live in a world of conspiracies anymore, our desire for conspiracy theories is endless.

Did Peter really think that things would simply go back to how they were before?

Why hadn’t an entire public relations plan been developed for the endgame?

Cunning and resources might win the war, but it’s the stories and the myths afterward that will determine who deserved to win it.

How one rides out the chaos in the aftermath of a deed is everything.

Winning, succeeding, pulling off the complex operation is the last step of one journey but simultaneously the first step in the next one, one arguably more import...

The next step is holding on to ...

Without a way out, tensions only increase and combatants have no choice but to fight on.

an army should not only leave a road for their enemy

to retreat by, they shoul...