In 2007, the website Valleywag, part of the Gawker family of gossip sites, outed Silicon Valley entrepeneur Peter Thiel as gay. Five years later, Gawker published a "highlight reel" of moments from a sex tape involving Terry Bollea, better known as Hulk Hogan, and the then-wife of his then-best friend, a tape which had been made by said friend without Bollea's knowledge or consent. Thiel, through intermediaries, secretly paid for Bollea's lawsuit against the website, a suit which ultimately resulted in a nine-figure judgment and the bankruptcy of Gawker. Conspiracy is the story of how all this transpired, a story involving a determined, methodical billionaire, a company of brash, arrogant bloggers, and an aging sports entertainment superstar with mountains of baggage. It's the story of why as well as how, and also the story of what happened after, when the conspiracy to bring down Gawker was revealed and a backlash began as the media came more and more to support Gawker's argument that journalists should be entirely free from any form of responsibility or accountability.
Holiday doesn't dwell on that last part, preferring to quote Machiavelli and ruminate on the nature of conspiracies. It might have been interesting to contrast this case to the lawsuits resulting from Rolling Stone's false accusations of rape by members of a UVA fraternity and the complicity of the college administration, which unfolded simultaneously with the Hogan-Gawker case but involved an establishment publication and lacked a crusading billionaire. Likewise, although he speculates as to whether the mainstream media would have been as sympathetic to Brietbart as they were to Gawker, he does not mention the demonstrated lack of sympathy when Matt Drudge was sued by Sidney Blumenthal a decade earlier. Indeed, while he states that "Champerty - the funding of lawsuits you have no direct interest in - dates back to at least medieval times", he cites no other actual instances, preferring to lament the outcome of the 2016 presidential election.
If Holiday seems uninterested in, or blind to, the similarities between this story and other recent legal and journalistic events, he more than makes up for it with his thoroughness telling the story he has chosen to tell. Remarkably, he was able to secure the cooperation of all of the principals and much of the supporting cast. One of the major themes of the book is the question of how much empathy a journalist should have with his subjects, and while no definitive answer is given, Holiday himself exhibits considerable empathy and an evident desire to treat his subjects fairly. At the same time, he keeps the narrative moving forward at a brisk pace, not always easy when dealing with years of interminable legal maneuvers.