Inside Peter Thiel and Nick Dentons Multimillion-Dollar War

Two surprise emails arrived in my inbox in the latter half of 2016.

Each was from a character who played the opposing roles in one of the most unusual conspiracies of recent history, and one of the most unbelievable stories of our time.

Not unlike the cowboys in your clich Western, these men found that the townwhether it was Silicon Valley or New York Citywas not big enough for the both of them.

Their gravitational pull would bring dozens of other people into their orbit over their 10-year cold war, along with the FBI, the First and Fourth Amendments, the professional wrestler Hulk Hogan, and soon enough, the president of the United States.

I am speaking, of course, of Peter Thiel and Nick Denton.

They had reached out to me over unrelated articles I published. Each wanted to talk about the conspiracy that had changed both their lives, yes, but about many other topics. It struck me that both men were somewhat lonely, and misunderstood people. Both were intrigued to hear that I was speaking to the other.

I only casually knew these two men who had spent the last few months in the headlines that had put Denton on the wrong end of $140 million legal verdict and Thiel in the crosshairs of every reporter in the world.

My own name had appeared on his websites, Gawker and Valleywag, a few painfully unpleasant times (and I myself had published my own criticism of Gawker as a media columnist). Until I had heard from them directly, I had no plans to write a book about either of them.

Soon I found myself in each of their apartments; first at Thiels in Union Square, where over a three course dinner prepared by the chef he travels with, Thiel revealed his painstakingly organized plot to destroy Gawker and the lawsuits he had instigated, funded and directed on behalf of Hulk Hogan and others in order to do it.

Then, 20 blocks downtown the next night in a $5 million apartment that had until recently been rented out to cover the mortgage while the courts decided whether he would be forced to sell it in bankruptcy, Denton hosted a salon of writers and thinkers to discuss the future of media.

Over breakfast the next morning, we began the first of many conversations about the events that had transpired from 2007 and continue to this day.

As I would come to find in my conversations, these figures were a study in contrasts: Denton, the thoughtful gossip merchant; Thiel, the aggressive philosopher strongman. Nick, the seeker of secrets; Peter, a believer in their power and sacredness.

Yet as different as they are, what I could not shake was just how similar they were: Both rich. Both foreign born, both immigrants who chased the American dream and bristled at convention. Both gay men with elite educations. Both free-market libertarians who distrust the system. Both buildersentrepreneurs. Both socially awkward, opaque, men that someone who spent time with both of them would describe as appearing to live inside their own sci-fi novel.

It would be as true for Thiel as it was for Denton, that their nearly unbroken string of success would make them both rightfully believe they were special and extraordinary.

So what brought these two similar men into conflict with each other? It was many things. But the most obvious, fittingly, comes from another similarity: Their shared tendency to say the things others wont say. Thiel, who founded The Stanford Review, a conservative paper which railed against political correctness, and Denton, who built Gawker into a $300 million company by publishing what other people wouldnt publish.

It was Denton, brilliant, mercurial, who first put the bodies into motion, pushing Owen Thomas, one of his writers at Valleywag, Gawker Medias Silicon Valley satellite, to cover the rumors that Thiel was gay. Thomas obliged. And on December 19, 2007 at 7:05pm, the site published this headline:

Peter Thiel is totally gay, people.

I would ask Peter why this bothered him so much, especially since he would admit that most of the people in his life, including his parents, already knew he was gay by 2007.

It was never about the Owen Thomas article, Thiel said. It was the Nick Denton comment.

It was like a full-on attack out of the blue. There was nothing I had ever done to these people in any way whatsoever

The day after the story broke, Denton posted a comment at the bottom of the piece which speculated about the reasons for Thiels privacy, that there was something strange about him for keeping his secret.

Whether one is sympathetic to this reading or not, it was clear to me that Thiel believed Denton had deliberately targeted him and implied he had psychological problems for not wanting to be public about his sexuality.

It was like a full-on attack out of the blue. There was nothing I had ever done to these people in any way whatsoever, Thiel would say to me.

Cicero once said that the beginnings of things are small. Indeed they are. The feelings of anger and powerlessness elicited in Thiel from that article and the subsequent comment from Denton were acute and they were painful, but they were not so overwhelming that they derailed Thiels life as an investor and entrepreneur.

Rather, they would sit in the back of his brain and stew for nearly four years, growing bit by bit with each follow-up story, and there would be many. About his life, about his businesses, about his friends, too. He would come to refer to Denton and Gawker privately as the MBTOthe Manhattan Based Terrorism Organization. He would also come to the conclusion that something must be done about them. But what?

And more importantly, why? Everyone Peter spoke to, including the well-connected New York City lawyer Eddie Hayes (I can get ya outta anything!), told him there wasnt anything he could do. So why bother? Why not sit back and count your billions?

Some have speculated that Thiel was motivated not by revenge or justice, but fear: fear of even more stories Gawker could write about him and his business interests.

But in fact it was a previously unreported conversation in Berlin that would really set in motion the conspiracy that has since received so much coverage.

At a dinner in 2011 with someone I have promised to refer to only as Mr. A, Thiel repeated the conclusion that hed heard from so many other people: that there was nothing that could be done about Gawker. (Editor's note: Buzzfeed has identified 'Mr. A' as an Oxford-educated Australian citizen named Aron DSouza.)

Mr. A, a short, brilliant law student, who friends would describe as a professional son for his skill at attracting powerful mentors, would look Thiel in the eye and say, Peter, if everyone thought that way, what would the world look like? If there were words better designed to prod a contrarian like Thiel into action, one would be hard pressed to come up with them.

Just hearing that was so refreshing, Peter would say later, because of course what you always heard was these incremental things that wouldnt quite do it.

Mr. As plan was cloak and dagger. Peter should create a shell company to hire former investigative reporters and lawyers to find causes of action against Gawker Medianot simply to harass or bleed Gawker, but with the intention of doing what no other critic or victim of Gawkers reporting had ever done before: Get in front of a jury. Mr. A. had researched some law firms, he had a timeline and a budget. Three to five years and $10 million.

Thus, Thiels vague idea to do something about Gawker was concretized into conspiracy on April 6, 2011 full year and a half before Gawker editor-in-chief A.J Daulerio received a set of hidden camera tapes featuring the wrestler Hulk Hogan that, in publishing, would give Thiel his opening to go after Nick Denton and Gawker legally. (Editor's note: Then-Gawker Media President and General Counsel Heather Dietrick is now CEO of The Daily Beast.)

If there is another difference between Thiel and Denton, its that in their strange unique ways one is an optimist and the other a pessimist.

If you can convince a jury in Tampa that this is not the way the technological future should look, they can tell history to stop.

One of Dentons writers would tell The New Yorker, Theres no point in writing about Nick if you cant get to the fundamental problem of his nihilism. Less judgmentally, Denton is simply an embracer of human nature rather than a challenger of it. Denton would describe his editorial style as, Give the people what they want, as shown by data.

I would ask Thiel why getting to a jury verdict was so important in his plan. After all, wouldnt it have been easier to just file frivolous lawsuit after frivolous lawsuit until Gawker was bankrupt? Or why not listen to the suggestion seriously put forward by his friend, the billionaire Sean Parker: Simply buy Gawker through a proxy and shut it down.

If you can convince a jury in Tampa that this is not the way the technological future should look, Thiel would look at me and say, they can tell history to stop.

Its not like Thiel was lacking in outlets, or the money to make new outlets if he felt his voice was not loud enough.

Talking with Nick, its clear he was, and continues to be, surprised that someone would be willing to take a belief this far. Wouldnt the libertarian solution, he told me, have been to make his own counterargument? To meet speech with speech. Its not like Thiel was lacking in outlets, or the money to make new outlets if he felt his voice was not loud enough.

What would have happened had Thiel tried to meet Denton in the open? I suspect he would not have fared well. Neither does Thiel. Hateful speech was their weapon and they were extremely good at it, Thiel would say, and I dont want to be fighting on their turf.

I came to think of it like a prosecutor wouldat the end of the day its not just between me and Denton. It was not just personal.

What I struggled with most in this story was that that these competing visions of the world were mutually exclusive and that for one to triumph, the other would have to be destroyed.

If someone has wronged only you and nobody else, maybe there is a question whether you should forgive them rather than insist on justice. But if theres a pattern of them doing it with many other people, I think that argues in a very different way, Thiel would say. I came to think of it like a prosecutor wouldat the end of the day its not just between me and Denton. It was not just personal, Thiel said.

Perhaps the The Count of Monte Cristo put it better, What a fool I was not to tear my heart out on the day when I resolved to avenge myself!

It was not just personal. I had to think about this myself. I spent many hours with Denton and grew fond of him. I saw the pain and resignation in himwhat the stress of a $100 million lawsuit must do to a person. I met his husband, his husband held my son. He came and visited me at my home, in the very room where I am writing this article.

Yet much of my book ends up being critical of him, or at least the toxic company he had created; the company where one writer would tweet, When I was at Gawker I wrote baseless posts accusing an actor of raping an ex-boyfriend. I did it bc my boss told me to, but I wanted to too.

Its up to others to have regard for their own emotional well-being. The job of a journalist would be unbearable if one was always to put oneself in the shoes of a subject.

Harshness deserved or not, I would take some solace from Dentons own words in his deposition in the Hulk Hogan case: My job is to disseminate information and manage an organization that disseminates information…Its up to others to determine the boundaries of acceptable social, ethical and legalistic norms…Its up to others to have regard for their own emotional well-being. The job of a journalist would be unbearable if one was always to put oneself in the shoes of a subject.

While this may not rise to the level of nihilism, as others had claimed, it is certainly pessimism of the highest order.

The central question of this whole story: Who was the real bully? Was it Gawker or was it actually Thiel? Was Thiel a righteous man who attempted to use his money to solve a problem that only power and money could solve?

After all, it was Gawker who long believed they were winning, who had not only published an illegally recorded sextape, but defied a judges order to take their article about it down. At one point in early 2013, they would threaten Hulk Hogan that this last chance to drop the case before they went after him for attorneys fees.

Or was it far more basic than that: a billionaire who destroyed a millionaire because he could?

Thiel himself would back Trump in the election. He rode the wave of Gamergate again, benefiting from the damage alt-right figures like Charles Johnson and Milo Yiannopoulos could do to his opponents. (Mr. A would describe Gamergate to me as largely autonomous but very helpful in their public relations campaign against Gawker.)

So Thiel pulled off two surprise victories, but at what cost?

Thiel might be gay, an immigrant, libertarian, and generally civilized and thoughtful, but the people on the alt-right he found as his fellow travelers were not. His arguments for Trump at the Republican National Convention were reasonable and counterintuitive. Theirs were not.

Trumps supporters used the same nastiness and traded in the same half-truths and identity-style politics that Gawker once had.

These people, Thiel would lament, six months into Trumps presidency, about the alt-right leaders he was now tainted with by association, they are the most like Gawker. Its not that they are willing to do anything in the name of the ideology, thats the ends justifying the means… The similarity is the nihilism: a mask for no ideology at all.

Thiel believed that Gawker was a scourge that, once eliminated, would allow for open, collaborative discussion. If anything, the opposite has happened. Trump would come to actively stymie expression, threatening to open up the libel laws in this country and pressuring NFL owners to fire the players who kneeled during the national anthem.

This must hit Thiel sometimes: that the man in the White House is essentially the opposite of everything he had spent his life believing in, a threat to the very libertarian freedoms and open civil discourse that Thiel had spent his money protecting.

Thiel and Denton at the end of this story would meet, twice in fact, first in a private home in San Francisco, then again later in the offices of a New York law firm.

How do you negotiate with a sociopath? That was the question at the back of my mind.

Picture these characters sitting across from each other: two men who had hated each other, made each other sick, spent north of $20 million battling each other, who had written and said such terrible things about each other. Denton characteristically is motivated by curiosity, and wonders: Who is this man?

Thiel for his part, tells me he expected to meet a sociopath, intent on manipulating him. How do you negotiate with a sociopath? That was the question at the back of my mind, he recalls. It is a question to which he actually had an answer. You have to box them in, and make sure they have no leverage, because they will look for a way to wriggle out and double-cross you in one way or another.

There are many people on many sides that aggravate me far more. There is some kind of meaning. We are similar in some ways and diametrically opposed in others. Its too uncanny not to have some narrative purpose.

Thiel clearly did not expect to see a human being walk in and sit down across from him. Denton, for his part, expected to find a domineering, angry man, not the almost bashful Thiel who only reluctantly makes eye contact. Its weird that I dislike him so little, Denton would tell me after. There are many people on many sides that aggravate me far more. There is some kind of meaning. We are similar in some ways and diametrically opposed in others. Its too uncanny not to have some narrative purpose.

The friend who had facilitated their sitting down would write Denton and Thiel in an email, Life is short and I want each of you to have happy, wonderful and long lives. For that reason I sincerely hope you two are able to resolve this conflict soon.

In October 2016 there would be a three-day meeting of all the lawyers in New York City to finalize terms. By November, everyone had been wrangled into the right place. Gawker Media would settle with Hulk Hogan for roughly $31 million. In March 2017, Denton settled with Hogan personally, who, by dropping the $10 million jury award against Denton, would let him emerge with roughly $15 million based on his shares in Gawker Media. The media firm Univision acquired Gawker Media for $135 million in a bankruptcy auction.

Was this victory? Was the world made better by what happened? I have gone back and forth many times in the research and writing Conspiracy about whether I agree with what Peter Thiel did to Gawker; whether it was Peter who was the bully or whether it was Nick Denton.

Maybe its a cop out, but I dont have a good answer. A mutual friend of Dentons and Thiels, not unsympathetic to either side, described the scenario as follows: You believe a restaurant across the street from your house is mistreating its employees, serving tainted food to its customers. You try to speak to the owner and are rebuffed. You reach out to the local authorities and hear nothing. You reach out to the local press and their stories have no impact. Might you then decide to take matters into your own hands?

Less than one third of 1 percent of his net worththats what Peter Thiel spent going after Gawker, a fraction of the interest his fortune would earn in a few days if it were in a bank account instead of under the purview of Mr. A, or on its way to the accounts receivable department at Charles Harders law firm.

Would it be wrong for you to spend a relatively trivial sum to do something you thought was important? Would it really make you a bad person if your efforts resulted in the restaurant closing its doors?

I can buy that.

But Id prefer to dodge the whole thing entirely. I ultimately tried to write a book about what happened, less so whether it should have happened. I can tell you that I was at least invigorated. There was something inspiring about these two larger-than-life figures, even if I disagreed with much of what they did. At least they werent playing it small. No one could ever accuse either of that.

Every conspiracy is the story of people. Nick Denton and Peter Thiel are two incredible people. It called to mind a line from Walker Percy, who said that he was neither a Democrat or a Republican but was nevertheless enlivened by the hatred which one bears the other. In fact, this hatred strikes me as one of the few signs of life remaining in the world. This is another thing about the world which is upside down: all the friendly and likable people seem dead to me; only the haters seem alive.

That strikes me as about as clear a conclusion I can take from the war between Thiel and Denton.

Ryan Holiday is the author of Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue.

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