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

by Ryan Holiday

A New York Times writer would later dub this ethos the “rage of the creative underclass.” A Gawker headline captures it better: “It’s OK to Be a Hater Because Everything Is Bad.”

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. Which is why it is usually the desperate who turn to conspiracy and why the powerful fear them so much.

When they didn’t know who was behind it—they assume it was Terry paying—they thought it was going to come to a point where he couldn’t continue anymore and had to raise the white flag.” It’s easy to miss this now that one side has won and the other lost—that long before that, one side was quite confident they were winning. 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.

Is it more than coincidence that Gamergate’s target was the same one that Thiel had in his sights?

In Florida, the law states that plaintiffs can’t recover damages for unintentional emotional distress in cases without physical injury. So Harder calls the insurance company and lets them know he’ll be dropping the claim, clearing the path for the insurance company to exit the conflict by 2015. 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. Now their war chest was depleted—they’d have to defend their story to that jury in Florida on their own.

“At some point the word ‘strategy’ becomes a euphemism for procrastination. A lot of different plans, a lot of different plans, and they will take a long time and you never—”

Over time, punching up turns into punching, period—at everyone and everything. Gawker’s growth would make it precisely what it criticized: powerful, unaccountable, unaware.

“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.

Before they depart there is a question. It brings both lawyers to the bench. 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?

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.

Way back at the beginning, Thiel and Mr. A decided on limiting themselves to ethical and legal means of remedy against Gawker, because as Thiel had said, secrets often have expiration dates. Mr. A had begun exploring bankruptcy lawyers in anticipation of a favorable verdict as early as 2015, but he had made fewer preparations for a favorable verdict where the curtain was pulled back and the puppet masters revealed. Where was the contingency plan? Why hadn’t a draft of the op-ed been written long in advance? 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.

Having actually gone through the system, Thiel would come to believe that maybe there weren’t enough lawsuits. That people should try more. And so he puts more money behind the idea, funding in 2016 a start-up called Legalist, conceived by a Thiel fellow, dedicated to bankrolling lawsuits with a high probability of winning and possibly setting new precedents.

Thiel’s victory over Gawker had proven Gawker prescient: that he was deserving of coverage and that people would love to hate him.

Mr. A would say, looking back, that perhaps their actions would have been better received had they not been stained with Trump, “but Peter endorsed Trump because of the trial. It gave him an appreciation for the dynamic of the country and for Middle America. I don’t think there is an alternate reality where he wins and doesn’t support Trump. I don’t think Peter Thiel would have been involved with Trump at all without this case.”

One of the worst things that can ever happen to a leader is to unconsciously associate resistance and criticism with opportunity. When everyone tells you you’re wrong and you turn out to be right, you learn a dangerous lesson: Never listen to warnings. And so the reason that few conspiracies are followed by additional successful conspiracies is because of this process and the changes that power produces.

Perhaps the most interesting unintended consequences, however, were the obvious ones. The ones that no one seriously thought could happen. First, the sex tape actually disappeared. Try to find it—I dare you. You can’t. The Streisand Effect now has at least one exception. Trying doesn’t always backfire.

We live in a world where only people like Peter Thiel can pull something so intentional and long-term off—and it’s not because, as Gawker has tried to make it seem, he’s rich. It’s because he’s one of the few who believes it can be done.