Portfolio, 2018, 336 pages
In 2007, a short blogpost on Valleywag, the Silicon Valley-vertical of Gawker Media, outed PayPal founder and billionaire investor Peter Thiel as gay. Thiel's sexuality had been known to close friends and family, but he didn't consider himself a public figure, and believed the information was private.
This post would be the casus belli for a meticulously plotted conspiracy that would end nearly a decade later with a $140 million dollar judgment against Gawker, its bankruptcy and with Nick Denton, Gawker's CEO and founder, out of a job. Only later would the world learn that Gawker's demise was not incidental--it had been masterminded by Thiel.
For years, Thiel had searched endlessly for a solution to what he'd come to call the "Gawker Problem." When an unmarked envelope delivered an illegally recorded sex tape of Hogan with his best friend's wife, Gawker had seen the chance for millions of pageviews and to say the things that others were afraid to say. Thiel saw their publication of the tape as the opportunity he was looking for. He would come to pit Hogan against Gawker in a multi-year proxy war through the Florida legal system, while Gawker remained confidently convinced they would prevail as they had over so many other lawsuit--until it was too late.
The verdict would stun the world and so would Peter's ultimate unmasking as the man who had set it all in motion. Why had he done this? How had no one discovered it? What would this mean--for the First Amendment? For privacy? For culture?
In Holiday's masterful telling of this nearly unbelievable conspiracy, informed by interviews with all the key players, this case transcends the narrative of how one billionaire took down a media empire or the current state of the free press. It's a study in power, strategy, and one of the most wildly ambitious--and successful--secret plots in recent memory.
Some will cheer Gawker's destruction and others will lament it, but after reading these pages--and seeing the access the author was given--no one will deny that there is something ruthless and brilliant about Peter Thiel's shocking attempt to shake up the world.
This was far more fascinating that I ever expected.
The short version of the story: In 2007, Gawker Media outed Peter Thiel, the billionaire investor who founded PayPal. Angered by this, Thiel embarked on what became a slow, patient campaign to destroy Gawker. The instrument of his vengeance, improbably, was Terry Bollea, better known as former professional wrestler "Hulk Hogan," who had launched a suit against Gawker for publishing a sex video of him banging his best friend's wife. Backed by Thiel's deep pockets, the Bollea lawsuit eventually ended the Gawker empire, driving it and its owner, Nick Denton, into bankruptcy.
That's the short version, but the long version turns out to be detailed, fascinating, and a far-reaching epic story that touches on political biases, the culture wars, and meditations on the nature of conspiracy and revenge.
Many people have opinions about the case based entirely on what they think of the principals.
Gawker was very much a "fake news" site. It put such tabloids as the National Enquirer to shame. They published some real news, but thrived on up-skirt shots, sex videos, and leaked photos of celebrities drunk, high, arrested, and in flagrante delicto. They didn't just pick on celebrities, though. They loved trashing sororities, and were perfectly fine publishing videos of drunk coeds being sexually assaulted. (No, that link does not go to a video. It's a NY Post article.) They just didn't care, because they knew no one could beat them in court, or spend the money it would take to try.
When Terry Bollea aka "Hulk Hogan" first won his lawsuit against Gawker, public opinion was generally in his favor. The trial had demonstrated vividly that Gawker didn't care in the slightest about truth or journalistic ethics. They would publish anything without regard for the impact on its subjects. The rich and famous were favorite targets, and everyone enjoyed the schadenfreude of seeing yet another celebrity being humiliated. Worse, they operated on the principal that they were essentially untouchable. "Never start a fight with someone who buys ink by the barrel" — they relied on strong First Amendment protections coupled with the fact that even for a rich celebrity, taking on a multimillion-dollar media empire was doomed to be a losing fight. Damning email after damning email, and worse, oblivious testimony by Gawker editors and writers, horrified the jury at how callously they disregarded ethics and privacy.
But when it was revealed that billionaire Peter Thiel was behind Hogan's lawsuit, essentially providing infinite funds in a deliberate effort to destroy Gawker, opinion turned. Thiel was not beloved by the media, and the fact that he was a libertarian, and later a Trump supporter, cast the case in a new light for many. Now it was a story about a vengeful billionaire crushing the freedom of the press for hurting his feelings.
Any such simplistic summary does not do the story justice, and Ryan Holiday, who interviewed both Peter Thiel and Nick Denton, among others, for this book (and in fact was asked to convey messages between them) does an excellent job of plumbing the psychology of everyone involved and laying out all the complexities.
Thiel, for example, wasn't just a thin-skinned billionaire out for revenge. At the time Gawker "outed" him, his being gay was already an open secret, known to pretty much everyone who knew him. So why was he so upset at the brief story on the Valleywag blog titled "Peter Thiel is totally gay, people"? There were a number of reasons, and none of them involved embarrassment or shame at being gay. Thiel, rich and powerful as he was, was genuinely afraid of Gawker, which seemed to have a hate-boner for him, and everyone told him there was nothing he could do about it; media organizations like Gawker could expose, humiliate, and mock anyone they wanted with impunity. He came to see Gawker as a genuine societal problem, and eventually, he was persuaded that not only should someone do something about it, but that he was that someone.
And yes, if you're wondering about all the other creative ways a billionaire could inflict retribution... Thiel thought about them, and discussed options with the chief architect of his campaign. Not purely out of scruples, they elected to follow a 100% legal strategy, eschewing even legal gray areas that Thiel could easily have funded.
Terry Bollea, meanwhile, comes off as very sympathetic and vulnerable in this tale. Sure, he was rich and famous. But he was also busted up after years of pro wrestling. His marriage had gone to hell, his wife ran off with a younger man and took most of his assets, his son was in prison, and when he went to his best friend's house for comfort and support, his friend's wife literally seduced him, and unknown to Bollea, the two of them were taping every encounter.
Bollea didn't even know this until years later, when the video fell into Gawker Media's hands, and they published it. When the story first came out, he lied, naturally, believing that such a tape could not possibly exist. He went on Howard Stern and claimed the "Man Code" would not allow him to sleep with his best friend's wife even if he had his permission. Not only did he learn in the worst possible way (via the media) what his ex-best friend had done to him, but everyone accused him of being just another celebrity has-been who'd released the video intentionally for publicity.
Worse, Bollea wasn't just taped having sex; he'd vented to his lover, said horrible things about his family in what he thought was intimate privacy, and most infamously, dropped repeated n-bombs when talking about his daughter's black boyfriend. When this came out during the trial, it essentially cost him what was left of his career.
Bollea was genuinely crushed by all these events. But by himself, he didn't really have a hope of winning. He wasn't nearly rich enough to take on the Gawker empire. Until Peter Thiel came along.
The ins and outs both of what preceded the Bollea lawsuit and what followed are truly a Machiavellian tale, because this really was a conspiracy. Bollea himself didn't know who the mysterious backer was who was pushing him to take his lawsuit all the way. Gawker was overconfident and would never have been destroyed this way had they known what was really behind the lawsuit; they assumed Bollea would eventually settle, because he had to. They made strategic errors that exposed them legally and financially because they didn't realize this wasn't a faux-outraged celebrity trying to get an apology, this was a billionaire trying to destroy them.
Enter GamerGate and the culture wars and then the 2016 election, and the judgment against Gawker became fraught with implications that went well beyond the politics of outing and whether or not it's okay to publish someone's sex video without their consent.
(Holiday does not miss the irony of Jezebel, a Gawker publication, being stridently anti-outing and anti-"slut shaming.")
If there's a flaw in Conspiracy, it is that the author tries a little too hard to tie everything to classical conspiracies, so there is an overabundance of quotes by Machiavelli and references to the Lincoln assassination and other conspiracies. (But in fairness, Thiel himself gave Holiday a copy of Machiavelli's works.)
I read this book mostly because I was a bit curious about the story, but it turns out to be truly an epic of modern journalism, American culture, and yes, illustrative lessons in how real conspiracies work. While years from now, this story will be a dated piece of history capturing this particular moment in time, I highly recommend it to anyone with any interest in contemporary politics, culture, journalism, Silicon Valley, celebrity media, or the mind of Peter Thiel.
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