Book Review: Conspiracy
Ryan Holiday was already my favorite author. But this book is beyond doubt the best of his that I've read. The Conclusion alone is some of the most brilliant writing I've read from any modern author. If I were a teacher, this would be required reading in my classroom.
Conspiracy tells the story of a plot ten years and millions of dollars in the making. It started in 2007 when Gawker published a story outing billionaire Peter Thiel for being gay. To Gawker founder Nick Denton, it was run-of-the-mill stuff. They published stories making fun of celebrities all of the time, outing closeted entrepreneurs, exposing the sins and vulnerabilities of anyone who had the misfortune of being targeted by them. Gawker’s justification was that if it was true, the world deserved to know it, and they expected the First Amendment right to free speech to keep them safe from any consequences of being the messenger. But Gawker was more than the messenger. They sought out and delighted in sharing the most humiliating moments in people’s lives, all for the clicks. Writers there were compensated for bringing in and publishing the most salacious gossip. The more controversial and scandalous, the better. Gawker was the schoolyard bully, and everyone in the media generally acknowledged it and took their blows with a “what can you do” shrug.
Peter Thiel decided to do something - not by “standing up” to the bully as is typically recommended, but by conspiring against it. He built a team to watch Gawker, waiting for them to really mess up, and when the opportunity came, they pounced. That opportunity came when Gawker published a short “highlight reel” of a sex tape of Hulk Hogan. The tape was filmed without Hogan’s knowledge or consent, and it was certainly sent to Gawker and then published without his consent. Legally, Gawker didn’t own the copyright to the tape, and they had no permission from the copyright holder or the subject, so they had no business posting it. One reason I found this story so interesting was that the opening Thiel needed to take his shot hinged on one simple law that I deal with everyday as an editor. The case went to court, and a jury in Florida decided once and for all that no one deserves to have themselves filmed against their will in their most vulnerable moments, and then have those moments broadcast for all the world to see. Gawker, its founder Nick Denton, and the writer who posted the highlight reel, A.J. Daulerio, were collectively fined over $115 million. It was Gawker’s death blow.
But Conspiracy is about more than just how, as the book’s subtitle tells it, one billionaire destroyed a media empire. It's about actions and their consequences, not just in a cosmic karma sense, but also in the sense that when one person does something, others can and will react. Peter Thiel did not wait for the arc of the moral universe to bring justice to Gawker; he conspired to bring it to justice himself. Whether that was right or wrong is endlessly debatable. Either way, Peter Thiel believed it was the only way to get it done. As Holiday explains:
The line from the Obamas was, ‘When they go low, we go high.’ It’s a dignified and impressive mantra, if only because for the most part, whether you liked them or not, it’s hard to deny that they followed it. But the now cliche remark should not be taken conclusively, for it makes one dangerous omission. It forgets that from time to time in life, we might have to take someone out behind the woodshed.
Peter Thiel was practical. He did everything legally, but he wasn’t going to sit around waiting for Gawker to come to its senses. After years of watching them, he decided there was no reasoning with this machine.
In ancient times it was the foolish sophists who believed that every problem could be talked through, that the logical, obvious, and right thing would simply come about if explained well enough. It’s the realists who know that this isn’t how things actually work, who know that realpolitik is how things actually get done.
It sounds like a simple story with a clear hero and villain - but, of course, it’s never that easy to assign roles in real life. Holiday fairly and compassionately represents all parties, including Nick Denton and A.J. Daulerio, who both take their punishment and choose to become better people because of it. And Holiday doesn’t shy away from detailing the conspirators’ personal faults. No one is purely innocent or purely guilty in this story.
I love that throughout the book, Holiday doesn't just give us the facts of what happened. He breaks down the anatomy of a conspiracy, like an omniscient sports commentator helping us understand the power plays and choices being made in the moment. The conspirators had so many options, a million different decisions they could have made, but Holiday is able to explain (with examples from other conspiracies) just why their plot was so brilliant - and why it ultimately worked. As he calls it, this is the "playbook" for Thiel's conspiracy - and possibly yours.
I’ll tell you now what most of the reviewers on Goodreads seemed not to like - which, incidentally, is what I loved most about the book. The Conclusion seeks to lay out the “lessons” that each character in this saga learned, and Holiday is perhaps heavy-handed in his moralizing. Personally, I appreciated that he laid out his opinion - take it or leave it.
At the end of the book, Holiday leaves us with an invitation: "What would the world look like if more people tried to change things, conspired to change things they found unjust, unfair, immoral?" It's a relevant question for our time.
