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Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue

von Ryan Holiday

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2307116,996 (3.88)1
An NPR Book Concierge Best Book of 2018! A stunning story about how power works in the modern age--the book the New York Times called "one helluva page-turner" and The Sunday Times of London celebrated as "riveting...an astonishing modern media conspiracy that is a fantastic read." Pick up the book everyone is talking about. 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.… (mehr)
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In the introduction to this book, Holiday makes this statement: "[I attempted] to make something more than just some work of contemporary long-form journalism or some chronological retelling of events by a disinterested observer (which I am not)." And then a few pages later, makes this contradictory statement: "In the meantime and for the record, I simply present what happened." I should have known what I was in for.

This book is very much a lionization of Peter Thiel. Holiday repeatedly avoids making judgments on what Thiel did, but simultaneously portrays Thiel as heroic. While at a private dinner party at Thiel's home after the trial, Holiday follows him on to the balcony and muses, "I stood a few paces behind and felt myself recalling the line from Hamlet: 'He was a man, take him for all in all, I shall not look upon his like again.'"

We are presented with a man who seeks revenge on someone who did him wrong, and ruminates, plots, and plans for 10 years, before finally slaying his nemesis; and yet we are expected to see him as someone who has seen a wrong in the world and righted it. Post hoc rationalizations and dehumanization of his opponent allow him to turn a personal grudge into a mission to make the world a better place. "'I came to believe that the nastiness of the internet was not a function of a technology or various things that have gone wrong, but the function of one particularly nasty media company led by a particularly sociopathic individual and that if I defeated Gawker, it would actually change the media landscape,' Thiel would say." To which my only response can be: How'd that work out, 5 years later? Is the media landscape a better place?

Holiday sees it this way: "what is indisputable is that he saw his actions as a kind of social good and there is something to be admired in that." How many evil acts in human history were committed by people who saw their actions as a kind of social good? Is there something to be admired in those as well?

I don't particularly care about Gawker, nor do I particularly care about Thiel. And I'm not even looking at the implications of a billionaire destroying a media outlet because he didn't like what they wrote about him. For this review, I'm just concerned about the book. It feels dishonest. As much as Holiday tries to act like he has no opinion of Thiel's actions, I think he's just maybe too timid to express his opinion directly. Instead, he writes things like this: "The line from the Obamas was 'When they go low, we go high.' It’s a dignified and impressive mantra, if only because for the most part, whether you liked them or not, it’s hard to deny that they followed it. But the now cliché remark should not be taken conclusively, for it makes one dangerous omission. It forgets that from time to time in life, we might have to take someone out behind the woodshed." ( )
  rumbledethumps | Jun 26, 2023 |
As someone who grew up in Pinellas County Florida, watching Hulk Hogan, spending a lot of time online during a time when Gawker Media sites were wildly popular and following Peter Thiel's career (and reading his book), every bit of this book was oddly familiar to me.

Conspiracy is a story about a lawsuit. That lawsuit is a claim by Hulk Hogan against Gawker media after they published a sex tape made without the wrestlers' permission. The lawsuit seemed like David vs Goliath, but in actuality, Hogan had the full backing by a billionaire to keep the lawsuit going.

I read Gawker back when it was running - usually when a scandalous story was linked to on Digg. This book turned that history on its head, causing me to realize just what I was supporting with those pageviews.

Although I don't back Thiel either. As a prominent Trump supporter, he lost all credibility with me as someone fighting against bullies.

Even with a cast of questionable characters, this story reads like a real-life version of The Count of Monte Cristo. ( )
  adamfortuna | May 28, 2021 |
The story behind the Hulk Hogan lawsuit with Gawker. The behind the scenes look at how and why this case took so long to get to court, the tactics used by both sides and the final results. ( )
  foof2you | Feb 8, 2021 |
An almost excellent book that makes valuable strategic and philosophical points using rather ridiculous material. Ryan Holiday is known for his writings on stoicism, so his decision to examine trashy celebrities and gutter gossip-mongers may seem peculiar. But there are valuable lessons to be learned in this mire of contemporary panem et circenses. Holiday's book is fast-paced, and appears to be consciously structured like a screenplay; it would make an excellent film. Some readers may be put off by Holiday's use of quotation and citation of precedent, but I usually find these 'interuptions' valuable. Unfortunately the book's final few chapters, which focus on Peter Thiel's involvement with Donald Trump, seem shoehorned in and mar the rest of the work. ( )
  Lirmac | Jul 15, 2019 |
Interesting book about conspiracy in general and the specifically about the destruction of Gawker media by Peter Thiel. I good book rendered slightly dull by the author’s rather pedestrian and lifeless reading of his own book. Maybe better read from the text, rather than to listen to it. Nevertheless some great insights. ( )
  jvgravy | Apr 4, 2019 |
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An NPR Book Concierge Best Book of 2018! A stunning story about how power works in the modern age--the book the New York Times called "one helluva page-turner" and The Sunday Times of London celebrated as "riveting...an astonishing modern media conspiracy that is a fantastic read." Pick up the book everyone is talking about. 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.

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