Our American Rome: On the Case of Peter Thiel vs. Gawker

We get what we deserve. In our conspiratorial times, it’s hardly surprising that we have books about conspiracies. Ryan Holiday’s new book, Conspiracy, focuses on the story of Silicon Valley venture capitalist Peter Thiel’s successful vendetta against the website Gawker. Holiday’s first bestseller was entitled Trust Me, I’m Lying. But in Conspiracy, everything Holiday tells us about Thiel’s meticulously planned plot to destroy Gawker—so he promises anyway—is true. 

Andrew Keen: In explaining how you chose to write the book, you say, “it somehow dragged me in, too.” But I can’t imagine you being dragged into anything you didn’t want to do. Did Peter Thiel or Nick Denton select you to write the chronicle of their feud? How and when did you realize that you needed to write a book about what happened?

Ryan Holiday: One of the strangest experiences of writing the book came when I was about two thirds of the way through reading what was close to 20,000 pages of legal documents. Attached as an appendix to a pre-trial motion with a series of tweets from one of Gawker’s editors was a tweet I had sent back and then a response from the editor to me. I had been researching the book for several months and interviewed all these people and then suddenly there I was actually in the legal record of the case. I’d also find out in interviews that articles I’d written about Gawker over the years had been read by the conspirators during their planning phase and then I think the weirdest convergence was when I was asking Peter about the decision to ask Charles Harder, the lawyer who had represented Thiel’s interest from the beginning, to step aside and let a local counsel make the arguments in the courtroom in Florida.

“If you want to win, ‘ego is the enemy,’” Peter said, “and the anti-ego thing we did was downgrade Harder’s role in the trial. Harder was not happy about this. It was the case of your lifetime and you get to have a much smaller part in it than you originally thought? But if we win, you get to take credit.” That phrase… I made it up! I wrote a book with that title. I was hardly dragged into writing the book, what I was referring to in that sentence was the way that somehow my writing and the ideas in my writing had unwittingly wormed their way into the actual events of the trial themselves.

When Thiel had reached out to me in 2016 to talk and that conversation had turned toward the idea of doing a book and when Denton had reached out to me about some other writing I’d do and I mentioned my plans to him, I certainly did not expect that months later I’d find this incredible coincidence. Maybe it was a matter of fate, I don’t know. Needless to say I’ve felt very tied to this book for a lot of reasons and the story is something still that consumes a good part of my mind. It just feels like something that should have happened in Shakespeare or Plutarch.

AK: Yes, the whole saga seems to have really resonated with your interest in the philosophies of both antiquity and the Renaissance, particularly in stoicism. It’s a bit surreal to read about Hulk Hogan’s sexual antics with his best friend’s wife interlaced with references to Seneca, Cicero and Machiavelli. So do you think there is something classical about the lingering animosity between Peter Thiel and Nick Denton? Is it a feud that would have been out of place in ancient Rome?

RH: It’s interesting to me just how shocked everyone was that a powerful billionaire would strike back against a media outlet that had so thoughtlessly and flippantly attacked him. I don’t think any good student of history should be surprised. In fact, the more you zoom out, the less remarkable these events from 2007 to 2016 really seem, or at least less uncommon.

If we changed the dates and names, and moved this story back to the Gilded Age, we’d think, “Man, Cornelius Vanderbilt did it again!” Or if I told you that this was the plot of one of Shakespeare’s plays, no one would bat an eye. In fact, I actually think you could make an argument that Nick Denton and Peter Thiel are so similar yet so different that they deserve the kind of treatment that Plutarch did in his Parallel Lives 2,000 or so years ago.

What I was trying to do in the book was correct a mistake I felt too many reporters had made covering the story which was to treat this as simply a matter of news rather than of history. To me this epic conflict, even if the stakes were relatively small, is a sweeping, timeless story and people would benefit from studying it. It’s got all the big themes of a Greek tragedy: power, sex, hatred, anger, fear, honor, greed, justice. My hope is that bringing in the quotes and stories from other stories, whether we’re talking about the Piso or the Pazzi Conspiracy or talking about the failed German efforts to assassinate Hitler is to give people a sense of those larger themes. I wanted to make them see that a lot of Peter’s decisions were straight out of Sun Tzu and Machiavelli, that this wasn’t this accidental thing but a very deliberate, strategic process. Some people will be horrified by what they see and others inspired, others cautioned. I think all those reactions are correct.

AK: At one point, you say that Peter Thiel’s strategic skills are “preternatural.” And in summing up Thiel, you quote Hamlet: He was a man, take him for all in all / I shall not look upon his like again. Do you think Peter Thiel is a genius? Are you a little bit in love with him—at least, platonically?

RH: Peter does strike me as the type of individual that would belong to a different era, when people were bit bigger, stranger, more Shakespearean, as we were saying. By any definition, Nick Denton is in the same class too, and that’s probably why it was inevitable that the two would find themselves in conflict. Can you really have two larger than life figures alive at the same time in the same industry? I think that goes to the Hamlet quote, which to me felt like the perfect place to end the book.

AK: Thiel is also a champion chess player and you present his conspiracy against Denton and Gawker as a form of chess. “Conspiracy,” you write, quoting Machiavelli, “requires patience and fortitude.” Your book, of course, is also entitled Conspiracy. Where does this story fit in our conspiratorial times? And how is to successfully orchestrate the kind of conspiracy that destroyed Gawker?

RH: It was a strange chess match between them because really it seems like for the most part Thiel was the only one playing. Gawker was so convinced that the First Amendment uniformly protected what they published that they did not conceive of any scenario where someone might be able to challenge them. If there was a person they were playing chess against it was Hogan and their playing style was mostly brute force. Gawker’s calculation was that an ordinary celebrity did not have the stamina or the money to litigate this case all the way to a jury—that eventually Hogan would wear down under the publicity, the pressure and the mounting legal bills. Thiel’s insight was that he understood Gawker’s playbook and simply changed the calculus by secretly giving Hogan (and other plaintiffs) limitless resources. He knew that it was only a matter of time before one of the cases got in front of a jury and that he’d get the verdict he was after. It’s ruthless, yes, but you can’t say he was incorrect.

The squeamish would look at what happened there and turn away because it’s unpleasant or cruel. I think the stakes are too high to do that. There are lessons in what happened, in how Thiel played the chess match. We live in this time where we think tweeting about shit or signing petitions or even crowdsourcing these large marches is what has an impact. Do you think Donald Trump cares about how many women attended the Women’s March? He doesn’t. It doesn’t apply any pressure to what he’s doing, because it’s not how he sees the world. He’s invulnerable to that kind of argument. Obama, sure, if a million people marched on Washington, he’d listen. Different problems require different solutions. Thiel realized that Gawker wasn’t going to be persuaded by public criticism or even a slap on the wrist. So he found where they were weak and hit them with his strength. I think we have other problems that require that kind of thinking. We need less tweeting, less public outage and more private scheming. Towards positive ends, obviously, and I’m not suggesting violence either, but Machiavelli wasn’t a bad dude. He was an astute understander of the dynamics of power and influence. We ignore him at our peril.

AK: It sounds to me that you are somehow justifying Peter Thiel’s well financed and carefully plotted efforts to put Gawker out of business. But what if he had done the same with The New York Times, The Atlantic or The Washington Post? Doesn’t your fetishization of Machiavellian strategy legitimize any kind of clever conspiracy? Couldn’t Donald Trump, for example, use the Peter Thiel playbook to destroy CNN? Indeed, some believe he is actually doing this in encouraging Justice Department’s efforts to hold up the AT&T and Time Warner merger. Peter Thiel might believe that the world is a chess match—but it’s actually more morally complex than that.

RH: That’s precisely the point. He couldn’t have put those publications out of business because those outlets don’t run illegally recorded sex tapes of celebrities (ones that were leaked to them by extortionists trying to leverage bad publicity into a payoff)! This is like saying someone got “taken down” for drunk driving or tax fraud. In some ways there is a pretty easy defense… Don’t drive drunk, don’t play fast and loose on your taxes. Is there some worry that we’re all vulnerable in some ways to these kind of back door tactics? Absolutely. I think that’s what makes this story both terrifying and fascinating.

I don’t think we have to worry about Trump and CNN, not simply because of their higher editorial standards but also because I don’t think Trump has the patience, the skill or the ability to work with anyone else. I worry that Russia turned Trump into an unwitting agent of their own conspiracy, sure, but I think the media is on safe ground. Remember, this was not a First Amendment case. This was a privacy case. It was made possible by a gratuitous violation of privacy done in full awareness of Hogan’s stated intention to sue, then followed by two ignored cease and desists, and then four years of litigation, in which Gawker had made early chances to settle or come up with a viable legal defense. In hubris and arrogance they did neither. I mention the Trump/Russia example because of course there are bad conspiracies. Harvey Weinstein clearly engaged in a conspiracy to silence victims and women. Booth conspired to kill Lincoln and several cabinet members.

But the word conspiracy is just a word. It matters what one does with it. America, like all rebellions, was a kind of conspiracy (the famous line, “We must all hang together or I suspect we should all hang separately”). Many of our most famous, precedent-setting court cases were conspiracies. Homer Plessy set out on that train hoping to be sent to a separate car so he could then sue with the help of a number of early civil rights groups. The effort didn’t succeed but if it had it would have been a brave conspiracy to strike a blow against segregation. John Boyd, the strategist, waged a conspiracy in the 1970s and 80s to attack bloat and bureaucracy in the Pentagon—and he had no choice but conspiracy because his opponents were corrupt and entrenched. Life is a chess match and the moral complexity is one of the dimensions. How we navigate that is up to us… and I suppose the people we pick fights with.

AK: You say trust with the reader is “paramount.” But if there’s one scarcity in today’s world it’s trust. Nobody seems to trust anything or anybody anymore. So how about a “conspiracy” to rebuild trust—trust in government, trust in media, trust in each other, trust in ourselves. Where should this conspiracy begin? And where might it end?

RH: I think it’s that last part that I was really trying to write about in the book. To me Conspiracy is in a lot of ways a book about human agency. You might disagree with what Thiel did, but this was a man who took control of a situation he found intolerable and changed the status quo. He said to me that he believed he could get this case in front of a jury, a case which to him represented the trajectory of privacy and technology, and that those jurors in Florida could tell history to stop. And that’s largely what happened, both the debate and the legal precedent about our right to privacy is largely changed as a result of this case. There is something inspiring in that to me.

My hope, however naive, is that people understand that that is what the book is about and they use it to good ends. When citizens are capable of doing no more than tweeting and complaining… of course our institutions are going to be rotted and corrupt. Why should they respect us? We have no power. Nor are we going to respect leaders or institutions with no agency themselves. To me this is also a book about competence. Gawker was reckless and incompetent. Thiel was ruthless and competent. One prevailed. In a weird way it would be alarming if the former had beaten the latter. I might not always fully trust competence, but I will at least respect it. I look out over our political and civic landscape and I don’t see a lot to respect (what’s that Nassim Taleb acronym IYI, Intellectual Yet Idiot?) To me that’s way scarier. I don’t completely know how to answer your question but I would say that such a conspiracy begins with people taking ownership and responsibility for their own lives… and doing something with it.