The Most Expensive Comment in Internet History?

Bollea v. Gawker isn’t just one of the most consequential lawsuits in the history of modern American media. It’s also probably the strangest. In 2016, Hulk Hogan, the professional wrestler, won a nine-figure lawsuit that ultimately bankrupted Gawker Media, a fleet of sites that epitomized the barbed brilliance of New York’s young media crowd. The lawsuit concerned a video of Hogan (né Terry Gene Bollea) having consensual sex with his best friend’s wife, while that same friend recorded the encounter—secretly, according to Hogan and later reporting. Behind the scenes of this tawdry affair, a more shocking story was playing out, in which Peter Thiel, the billionaire investor, seemed to be exorcising a deep grudge against Gawker by bankrolling Hogan’s lawsuit to destroy the media company that published the sex tape.

This saga is the subject of a new book by the author and (controversial) media strategist Ryan Holiday, called Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue. Shortly after the verdict, both Thiel and Gawker’s founder, Nick Denton, reached out to Holiday about his coverage of the lawsuit in the New York Observer. Over the next two years, Holiday turned that access into the first reported book that chronicles the lawsuit, from the offending blog post that sparked Thiel’s wrath to the aftermath of Gawker’s sale.

In the book’s biggest revelation, Holiday reports for the first time that a twentysomething acquaintance of Thiel’s, identified only as Mr. A, not only came up with the idea in April 2011—before the publication of the Hogan video—to target