Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue 
By Ryan Holiday
Portfolio. 335 pp. $28

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Reviewed by

Alyssa Rosenberg

nolead ends Conspiracy chronicles the legal battle between Terry Bollea, better known as professional wrestler Hulk Hogan, and Gawker Media, the swashbuckling Manhattan publishing group founded by Nick Denton. Author Ryan Holiday argues that the story shows how effective conspiracies are - but the book actually shows the opposite.

In 2012, A.J. Daulerio, then editor of Gawker's flagship site, published excerpts of a sex tape, recorded in 2006 without Bollea's consent or knowledge, that showed Bollea in bed with Heather Clem, then married to Bollea's best friend, radio personality Bubba the Love Sponge.

The story may seem wacky already, but this is when it gets truly weird.

In 2007, Gawker Media acquired a powerful and patient enemy when one of its writers outed PayPal founder and venture capitalist Peter Thiel as gay. Gawker's Denton, who, like Thiel, is gay and libertarian, believed Thiel's refusal to be open about his gayness was proof Thiel was "paranoid." To Thiel, the story was a terrible violation.

But it took him four years to strike back. In 2011, a Mr. A, whose role is first described in Conspiracy but who remains a shadowy figure throughout the book, persuaded Thiel to devote $10 million and five years to a shell company aimed at finding and backing potential lawsuits against Gawker. Among their beneficiaries: Terry Bollea. In 2016, a Florida jury awarded Bollea damages so punishing that Denton had to sell the company. On the surface, it seemed Thiel's conspiracy had checkmated Gawker Media.

But Thiel's conspiracy failed: He killed Gawker, but in doing so undermined his dream of making the internet a more decent place and securing his own privacy. By contrast, Gawker was destroyed not because its leaders failed to conspire, but because they didn't pursue the transparency they claimed to believe in.

Thiel's taste for conspiracy gave the impression that he had lots to hide. When he came forward after the verdict to acknowledge that he had funded Bollea's lawsuit, it became clear he had been plotting revenge for nearly a decade - and that made him seem vindictive and obsessive. These uncontrollable audience reactions gave him unwanted celebrity.

Holiday acknowledges some of these problems, but he does not acknowledge the ultimate failure of Thiel's conspiracy. To do so would be to admit that Conspiracy doesn't come close to proving Holiday's most ambitious argument.

If transparency might have served Thiel better than conspiracy, a full dedication to its stated values might have saved Gawker, too. In contravention of his company's crusading reputation, Denton refused to have his reporters pursue rumors that Bollea had a powerful financial backer because, as former Gawker executive editor John Cook said, "he did not want to get wrapped in any kind of conspiracy theories."

Had Gawker chased down proof that Bollea's lawsuit was the work of an extraordinarily wealthy man stewing over a smaller slight and reported that before the case went to trial, it would have entered the arena on far different terms. As Holiday notes, breaking that story would have bolstered Gawker's claim to be a serious journalistic outlet.

Thiel himself might have benefited from choosing transparency over conspiracy. By the time he did identify himself as Gawker Media's nemesis after the verdict in Bollea v. Gawker, the narrative of the trial was well on its way to being set. Thiel discovered it's difficult to come forward and insist you're the hero of the story when you've already won the sort of victory that makes the public inclined to believe you're the villain.

"Cunning and resources might win the war," Holiday writes toward the end of Conspiracy, "but it's the stories and myths afterwards that will determine who deserved to win it." The flaw in Thiel's thinking, and in Conspiracy, is in failing to recognize that the stories and myths that emerge after an event often are the substance of the victory.

This review originally appeared in the Washington Post.