Conspiracy

What’s it about?: Silicon Valley investor and entrepreneur Peter Thiel, professional wrestler and television personality Terry “Hulk Hogan” Bollea, and their blockbuster takedown of Gawker Media and its founder, Nick Denton. Although, you can’t improve on the very first paragraph:

“This is the story of a conspiracy, the story of a billionaire who set out to make an example of a millionaire, to destroy the man’s life’s work in response to a cruel transgression made as thoughtlessly as it was quickly forgotten. It is a story of poetic justice on a grand scale, plotted silently for nearly a decade. It is also a book about that controversial word and method – conspiracy – which has long terrified and intrigued.”

My opinion: Conspiracy is very different from Ryan Holiday’s usual fare, but he cites it as the book he is most proud of, and I can see why.

He is best known for his books on Stoic philosophy, most notably The Obstacle Is the Way, and Ego is the Enemy. Conspiracy sort of came to him by accident. It was the result of Holiday being approached by Thiel and Denton, on separate occasions. Each were impressed with his writing – whether it be his works on Stoicism or his writing on the case – and wanted to share their views of what had happened.

To document Bollea v. Gawker would have been no small feat for any author. As Holiday recalls, “It was outside my wheelhouse; it would be a ton of work; it would be the kind of project that would upset a lot of people. And frankly, it was personally quite risky… to be writing about a powerful gossip merchant and a right-wing billionaire who had just shut down a media outlet he didn’t like.”

To imagine what he must have felt, being in a very unusual (but probably exciting) position. Nobody could blame Holiday for being hesitant to take on such a task, but in the spirit of growing from challenges, he did. Twenty-five thousand pages of legal documents, and interviews with the key players – Thiel, Hulk Hogan, Denton, editor A. J. Daulerio, attorney Charles Harder, and Thiel’s operative known only in the text as “Mr. A” – provide more than enough source material. Combine this with the ideas of a broad church of thinkers – including Cicero, Seneca, Niccolo Machiavelli, Soren Kierkegaard, and many others – and what you have is not merely a retelling of events, or a work of long-form journalism, but a story that serves as a springboard to address a wide range of topics, including power, agency, strategy, privacy, and the economics of online media. It really is an essential text for our time, with so many lessons to be learned – from the story itself to the very idea of conspiratorial justice as a concept.

I’m no forecaster, but I knew this book was going to be a wild ride when it was first announced. Having something of a perverse interest in the economics of online media, I had followed Bollea v. Gawker in the news. I read Holiday’s Observer column regularly, and Trust Me, I’m Lying was (and still is) in my top ten books.

I pre-ordered a copy, and when the day of arrival came, I was so excited I stayed home from work. Waiting for this book felt like Christmas (minus the huge lunch, catching up with relatives, and whathaveyou). As a kid, did you ever pine after something really badly – a new album or an action figurine – but once you got it, it was never as good as you imagined it to be? Well, Conspiracy was the opposite. It was so much better than I could ever have imagined. No book before or since has resonated with me the way this one did; it embodied everything I like in a text, and blended it all seamlessly.

Going into it, I had expected Holiday’s portrayal of Gawker and Denton to be damning, given his coverage of the case as it developed. However, Conspiracy takes a different approach. Nobody is the hero; nobody is good or bad in black-and-white terms. There are many grey areas, and Holiday does well figuring Thiel and Denton as dual-protagonists rather than your cliched good and bad guys.

Perhaps the best takeaway, relating to power and agency at least, to quote the philosopher Nassim Taleb and his reaction to the book:

“You will go nowhere signing a petition or writing op-eds.”

In Skin in the Game, Taleb wrote that the press would inevitably self-destruct, given problem of the press acting against the public who had sided against Gawker:

“One way journalism will self-destruct from its growing divergence from the public is illustrated by the Gawker story. Gawker was a voyeurism outfit that specialised in publicising people’s private lives in industrial proportions. Eventually Gawker, which bullied its financially weaker victims (often twenty-one-year-olds in revenge porn scenes), got bullied by someone richer and went bankrupt. It was revealing that journalists overwhelmingly sided with Gawker on grounds of ‘freedom of information,’ the most misplaced exploitation of that concept, rather than with the public, who sided, naturally, with the victim. This is to remind the reader that journalism has the mother of all agency problems.”

Something in Holiday’s work must have resonated with Taleb, but that’s a separate discussion.

Described by the New York Times as a “profound masterwork,” and a “genuinely startling proposition” by the Washington Post, Conspiracy really is a story of our time. The limits of the internet, of freedom of expression, and an individual’s freedom to simply have a private life, are themes that cannot be ignored. If you’ve ever found yourself wondering how we went from the “good old days” to the hyperreal media circus that is the present, it’s a must-read.

It might not be the best book of all time in the accepted sense, but it’s my personal favourite. Whether it’s ruthless, or brilliant, or both, Thiel’s plot against Gawker is fascinating almost for the sheer audacity of it, and Holiday’s retelling puts everything so eloquently. Compelling and polished!