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

by Ryan Holiday

Yet here they were, using them not as their main strategy but as a kind...

That is the idea. To push them beyond their capacities so they would begin to make mistakes, begin to question even their own judgment.

At one point, every legal mind in the country thought the Hogan case was weak—only in pursuing it,

only in persevering through discovery did it begin to come together.

Because under attack, sustained and comprehensive attacks, organizations and opponents begin to buckle.

it’s more important what they are not doing, what they don’t have time to do as they deal with all of it:

Gawker is not preparing for trial.

This is the problem with making enemies, with generally treating everyone with contempt and creating a culture of fear.

They despair of revenge until you are weak and vulnerable. They look forward to the day when the tables are turned.

“At some point the word ‘strategy’ becomes a euphemism for procrastination.

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

The secrecy of a conspiracy and its execution, then, is not purely a matter of planning and discipline,

but also a matter of the bonds that bind the conspirators together.

culture eats strategy.

It’s a truism that applies as much to conspiracies as it does to

busin...

Over time, culture can sour.

Gawker’s growth would make it precisely what it criticized:

powerful, unaccountable, unaware.

It’s the writers who stayed, year after year, then, who defined the culture.

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

So when someone like Cook wrote a blog post, essentially telling the judge to go to hell in 2013,

he was drawing a line in the sand that everyone else at Gawker had to toe, to their eternal public relations regret, and creating a headwi...

Culture eats strategy.

He had begun to despair of convincing his writers, the misfit toys he had made

a home for, of their apocalyptic reality. He knew that a loss in court could likely be the end of the company he’d built, the end of meetings for that writer to live-tweet, the end of a carefree environment that would tolerate that kind of insubordination.

He would try to push the writers to be nicer, to ask them when they would be gratuitously mean or reckless, “What’s your purpose here? What are you hoping to do with this post?” He thought he could manage the energy. He tried new editors, wrote long memos, held long meetings about his editorial vision.

But the incentives were built into the core of the company.

The writers had no stake in the business, only in the notoriety. They were measured in page views, and they knew the best way to get them was to say and do ...

It never occurs to anyone at Gawker how easily such a gesture would have frayed the bonds that tied its enemies together.

An apology would have sapped the conspiracy of its power

But to apologize they would have had to see themselves from another perspective, an unbiased and human one that was capable of wrongdoing and meanness, and they couldn’t.

Rich donors are notoriously easy marks. They fund boondoggles as often as they

fund the efficient, ruthless machines that people fear are running the world. It’s a real-life luxury tax.

Limitless resources are corruptive. They ma...

If Denton is a prisoner on his own ship, then Thiel, too, in his capacity as Ahab, is a prisoner of momentum.

He has to keep everyone interested in the hunt.

Without a blinding hatred for the enemy as motivating fuel or without the absolute power of a leader, conspiracies fall apart under the pressures of the long journey.

what ties them together really is Gawker and what they’d come to feel about it.

Gawker had not only incited a conspiracy, but in the course of the trial, its actions, its tone, its arrogance had fused its unknown, unnamed opponents together.

So many papers were filed in this case that it overwhelmed the underbudgeted Pinellas County court system, leaving the judge to sheepishly ask that the lawyers print an extra copy of each document and provide her with one.

They had been at this not for months, as Gawker might have expected, but years.

The issues were driven in a feedback loop of tit-f...

No issue was too small, nothing had been left unexplored.

Each of these disputes, played out in hundreds of motions and responses and motions in response to responses to motions, was litigated by people who had to be paid and who were happy to keep earning their fees.

The result is billing that almost boggles the imagination.

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

Just as conspiracies are rushed forward by events, they can be interminably delayed and disrupted by them.

It’s the moment in between those buckets when a conspiracy is most vulnerable, because the combination of stasis and exposure begins to evaporate those ties that bind. But even more than that, it is here that one has the brief time to reflect and consider:

Is it worth another try? Do I have it in me?