A review by dannberg
Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue by Ryan Holiday

4.0

This is a highly engaging and educational read, with a few fatal flaws that kept me from completely loving the book.

Holiday has learned a lot from his mentor, Robert Greene, and this book feels a lot like 48 Laws of Power. It's the story of Peter Thiel's lawsuit against Gawker, yes, but it's also about the history of conspiracies in general. Using the narrative framework of "conspiracies" brings a lot of extra value to what would otherwise be a story better suited for a longform journalism piece, rather than a full book. The fact that the conspiracy against Gawker was revealed in such a detailed way made me think critically about other current events, and how they too played out.

But as I mentioned, I couldn't help but feel that there were some fatal flaws in the book, the biggest of which is that the story fully fleshes out Peter Thiel's point of view, but we're left seriously lacking when it comes to Gawker. As an occasional reader of Gawker, I found them to be an incredibly complex organization. Holiday mentions briefly how sometimes news that broke on Gawker would be tomorrow's headlines, but doesn't dive into any of the articles or pieces that had a positive impact. While I'm not attempting to argue that the good things made up for, or even balanced out, the bad, but the image painted of Gawker is one sided: Thiel's side. For example, one could argue that Reddit's big reforms to remove "jailbait" (and other controversial) content from its site was a direct result of Gawker's reporting. Exploring stories such as these would have made Gawker a more well-rounded character in the story. Instead, it presents the organization as hiding behind the moniker of "free speech" and harboring angry and spiteful journalists. The truth is way more complicated.

Also, there was one section that I found extremely trouble, but was quickly brushed over. As another reviewer pointed out, there were hints of a possible connection between Thiel's posse and Gamergate. This, to me, needed way more investigation and fleshing out, because the implications are huge.

Holiday discusses the struggles that he had with trying to be impartial, especially when you're working with your subject matter in such a personal way (the book is a result of several lengthy interviews with almost all the main players). It's as if he knew what people's issues with the book were going to be, and was already trying to explain his reasoning.

But this section also serves to humanize the author. It's a flawed story about one flawed character utterly destroying another flawed character. It's also a quick and very entertaining read. So I do recommend the book despite it's flaws.

History really is written by the winners.