Billionaire hides behind wrestler to mount epic grudge campaign against website he feels has offended him

Even billionaires, busy living their every fantasy, have discovered that satisfying one’s every whim might still take work and patience to achieve. Not everything is available on a silver platter.

Some billionaires are fine with work and patience though. Those qualities may even have been two of the reasons they became rich in the first place.

Peter Thiel, whose bank account was bulging with billions made from Paypal and Facebook, was quite happy to work and wait after taking volcanic umbrage at a story that the Gawker gossip website ran about him in 2007,

He thought the headline “Peter Thiel is totally gay, people,” might affect the way he was perceived as a titan of technology investment.

And according to Ryan Holiday, Thiel was moved to further incandescence by a comment that Gawker proprietor Nick Denton had made in the comments section of the story, implying there was something wrong with Thiel for wanting to keep this information private.

To get a sense of just how cross Thiel was about this attack on control of his own story, in 2009 he compared Gawker to al-Qaeda. “I think they should be described as terrorists,” he said. “I don’t understand the psychology of people who would kill themselves and blow up buildings, and I don’t understand people who would spend their lives being angry.”

Thiel himself, though, was quite happy to spend the next few years keeping an ember of anger burning while he waited for an opportunity to topple the formidable, confident and aggressive Gawker operation.


Conspiracy, by Ryan Holiday (Profile Books, £14.99)


So there’s your battle – which side do you take? The freedom of the press to say whatever they want, however offensive and personally damaging some people might find it? Or the freedom of billionaires to defend the rights of others to keep aspects of their lives private when it coincides with their own interests?

Holiday tells this legal and personal drama exceptionally well, even if he never misses an opportunity to swerve into the thoughts and deeds of great generals, ancient Greeks and all your favourite other sources of historical wisdom to illuminate his point that this is not any old court squabble.

It is, to his great delight, a conspiracy, something to be admired for its rarity alone. Even opportunities to put one together are unusual, and they are complex, expensive, hard to sustain, and some big mouth always blabs and ruins it anyway.

Thiel knew he couldn’t just sue Gawker over what they had said about him. After all, it was true. He had to identify a much more destructive strategy, and it found him, when he met with an ambitious young graduate called “Mr A”.

His idea was to find instances where people had been wronged by Gawker and for Thiel to fund actions against the website from the shadows. Cases that Gawker could defend on first amendment – free speech – grounds were unlikely to help them much. Too hard to win. Then, in October 2012, Terry Bollea, better known as Hulk Hogan, fell into their lap.

The great wrestler had been secretly filmed (by his best friend) having sex with that best friend’s wife. Gawker had run “a highlight reel” and refused, at first, to take it down when asked by lawyers.

Thiel had his case: invasion of privacy, and spent years hidden behind lawyers piecing a strategy together; refusing deals, assembling material, manoeuvring the case to Hogan’s home district in Florida where he enjoys godlike status, and even staging two secret dummy trials, with judge, jury and a full supporting cast, to make sure their case was strong. (From this experience they discovered which type of juror was most likely to side not just against Gawker, but to be most outraged by their behaviour and therefore award the highest damages.)

Gawker, used to being able to wear out potential litigants, was massively overmatched. By the time it was over, they were facing $140m in fines, the business was sold, the flagship website closed and Denton in chapter 11 bankruptcy.

Is it right for a rich man to be able to shut down a pesky media operation to settle a grudge? Or did Gawker deserve everything they got for being so cavalier? You decide, but one of the strengths of Conspiracy is that it’s not a straightforward call.

Either way, if you like your dishes of revenge served not so much cold as straight from the freezer, Conspiracy will meet your needs deliciously.