When Terry Bollea walked to the front of the courtroom on the fourth floor of the Pinellas County courthouse on March 7, 2016, he was just a shadow of the man he used to be—the man the world knew him as: wrestling superstar Hulk Hogan. Orthopedic surgeries had reduced his once-plucky stride to a limp. Crises and sadness had beset his personal life over the previous decade: His son and reality-TV co-star, Nick, had gotten into serious legal trouble when he crashed his car in 2007, nearly killing a friend in the passenger seat. Bollea’s conversations with Nick in prison had been leaked to the media and he’d had to pay millions to the victim’s family. Bollea’s marriage, long faltering, came to a painful end. He briefly contemplated suicide.
Bollea persevered: He remarried and seemed to put his life back together—but more humiliation was in store. In 2012, an old video of him (dating from years earlier, when he was having affairs during his crumbling first marriage) was published on the celebrity-gossip website Gawker. The recording showed Bollea and Heather Clem—wife of his best friend, the radio host known as “Bubba the Love Sponge”—having sex.
Bollea, devastated, decided to sue Gawker Media and its proprietor Nick Denton. And his announcement to reporters of his intention to take legal action brought him to the attention of people secretly hoping to find someone just like him. These “conspirators,” to use the word preferred by author Ryan Holiday, wanted to bring down Gawker and saw Bollea as the perfect means to that end.
The story recounted in Holiday’s book Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue—a timeless tale of revenge, with countless precedents in history and literature—really begins in 2007, when a Gawker Media publication, Valleywag, ran an article titled “Peter Thiel is totally gay, people.” A cofounder of PayPal and early investor in Facebook, Thiel was then already a major player in Silicon Valley. Although his sexual orientation was known in his immediate circles, it had not yet been made public. But it wasn’t the outing that most irked the tech investor; it was, Thiel would later tell Holiday, a comment that Nick Denton left beneath the Gawker story: “The only thing that’s strange about Thiel’s sexuality: why on earth was he so paranoid about its discovery for so long?”
Like Thiel, Denton is a gay, foreign-born, free-market libertarian. Like Thiel, he had a litany of entrepreneurial successes to his name. He had founded Gawker Media as an outlet for his two loves: gossip and technology. Now he had challenged Peter Thiel by not only outing him as gay but by implying he was somehow ashamed of it.
This was too much for Thiel. Gawker could not be allowed to attack him with impunity. It had to be taken down.
The “conspiracy” of Holiday’s title arose when Thiel met with a 26-year-old, Oxford-educated lawyer from Australia whom Holiday calls “Mr. A.” Over a meal in a Berlin restaurant, Mr. A explained to Thiel that he had a blueprint for destroying Gawker, and even presented Thiel with a timeline and budget: “Three to five years and $10 million.” After some deliberation, Thiel decided it was worth a shot. He retained an experienced Los Angeles lawyer, Charles Harder—now an attorney for Donald Trump—and together the three men began devising a strategy for attacking Gawker in the courts.
They started with research. Since its founding in 2003, Gawker had racked up an impressive record of sleazy reportage. Holiday offers a sampling of the website’s headlines: “Christina Hendricks Says These Giant Naked Boobs Aren’t Hers, But Everything Else Is”; “Olivia Munn’s Super Dirty Alleged Naked Pics”; “Anderson Cooper Is a Giant Homosexual and Everyone Knows It.” Publishing illicitly obtained sex tapes was fairly typical. Once, Gawker posted a video of a college-age girl having sex on the floor of a bar bathroom. When the girl complained and asked for it to be removed, the site’s editor replied, “I’m sure it’s embarrassing but these things do pass.” On another occasion, after the site released a sex tape showing Limp Bizkit singer Fred Durst, Durst sued—but soon withdrew his suit and sent Denton an apology with fresh-cut flowers. Durst didn’t have the resources, patience, and co-conspirators necessary to take on Gawker.
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Holiday was well positioned to write an account of the destruction of Gawker Media. Although he’s only 30 years old, he’s already had an unusually eventful life. After dropping out of UC Riverside at 19, he became the youngest executive at a Hollywood talent agency and a research assistant for Robert Greene, bestselling author of such books as The Art of Seduction and The 48 Laws of Power. By 21, Holiday was the director of marketing at American Apparel; he worked for the controversial clothing brand through many of its successes, only leaving after its founder Dov Charney was dismissed in 2014 for sexual harassment.
Even during his time at American Apparel, Holiday took on a number of outside publicity-consulting jobs for entertainment figures. He also began writing copiously, and in 2012, his first book was published: Trust Me, I’m Lying, a confessional about his dishonest stunts in media. (It opens with the story of how he helped generate publicity for “fratire” author Tucker Max by secretly defacing a billboard for Max’s upcoming movie, then pseudonymously sending pictures of the vandalism to bloggers who activated the outrage machine.) The book quickly became a bestseller.
Most of Holiday’s subsequent books—he has written a total of seven—have dealt with stoicism, the classical philosophy that he came to embrace as he sorted out his life. Today, Holiday lives on a farm outside Austin, Texas, where he keeps cattle, donkeys, and goats, and from where he runs a creative agency.
So Holiday has seen moguls rise and fall, he is intimately familiar with the unseemly, exploitative, and dishonest side of entertainment and marketing, and he is inclined to philosophical interpretations of events. All this left him well situated to write about Gawker, its demise, and the aftermath. Apparently after some of his thoughts about Bollea v. Gawker were published in the Observer, Thiel and Denton each independently reached out to Holiday to discuss the story. Their conversations with him became the main substance of the book.
Holiday describes how, with Thiel’s secret underwriting and Harder’s legal help, Bollea—one of several potential Gawker-killing litigants the conspirators tried to push—fought Denton and his company. By the time Bollea v. Gawker and the subsequent appeals and negotiations ground to a close, the morally bankrupt Denton and Gawker Media were both financially bankrupt, too.
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Holiday is not much concerned with the public implications of the Gawker case, which at any rate remain unclear. At first, public opinion seemed to be in favor of the little guy trying to take down the sleazy media company. But since Thiel’s bankrolling of the case was revealed, there has been considerable hand-wringing in the press about what it means for wealthy people to use litigation to strike out at publications. Holiday has little patience for such concerns:
Which isn’t to say that Holiday is entirely unsympathetic to Denton and Gawker. He acknowledges that Gawker‘s callous style “had occasionally yielded results” and that there might be unintended consequences if media organizations feel reticent to cover wealthy or powerful people because of the potential threat of litigation. And the push to soften up journalism, too, could be harmful; in one of their exchanges, Denton would state, “The pressure for journalists to show empathy has a cost.”
Holiday’s chief interest isn’t really the substance of the conspiracy he describes but rather the notion of conspiracy itself. As he guides readers through the synapses of the retributive psyche, it is hard not to raise your eyebrows at his intimate understanding of the patience, cunning, and ruthlessness required to meet one’s conspiratorial aims. After all, he himself was once a conspirator, a man who operated in media’s subterranean level. If his views on the Gawker takedown are fairly neutral, his views on conspiracy are overwhelmingly positive:
Elsewhere he asks rhetorically, “Was the founding of America not a kind of conspiracy?” He then goes on to describe other prominent conspiracies and conspirators in American history, working both for good (like Lincoln, in his efforts to pass the Thirteenth Amendment) and for ill (like the 1933 fascistic “Business Plot” aimed at overthrowing President Roosevelt).
Holiday is obviously using the word “conspiracy” capaciously here—probably too capaciously. Aspiring to change society is hardly the same as covertly scheming. Holiday says that “the word is neutral, the application is not.” But the word isn’t simply neutral; in ordinary usage, it has negative connotations, and for good reason. In liberal democracies, conspiracy is a fear of the average citizen—that the powerful will manipulate or deceive the people. We Americans are especially wary of conspiracies, to the point where we often imagine them even where they aren’t. To affirmatively embrace conspiracy is to encourage that paranoia, and to endorse, at least tacitly, the secretiveness and dishonesty that conspiracies often require.
Still, despite those significant moral drawbacks: Sometimes a conspiracy is the wisest, or even only, way to achieve good ends. Consider Holiday’s account of the very moment of first conspiring, when Thiel and Mr. A are having their initial dinner. Thiel “repeats the words he has been told by so many others, so many times—that there was nothing that could be done” to destroy Gawker. Mr. A responds: “Peter, if everyone thought that way, what would the world look like?” When all other options seemed closed off, when all publicly visible and democratically licit approaches seemed impossible, one option remained. Sometimes it just takes a little conspiring to make the world a better place.
Dylan Croll is a College Fix fellow at THE WEEKLY STANDARD.
