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

by Ryan Holiday

There is a moment in The Great Gatsby when Jay Gatsby introduces Nick Carraway to Meyer Wolfsheim, mentioning offhandedly that he is the man who fixed the 1919 World Series. The idea staggers Gatsby’s idealistic young friend. Of course, Carraway knew the series had been thrown. But “if I had thought of it at all,” he says, “I would have thought of it as a thing that merely happened, the end of some inevitable chain.” It was unbelievable to him then, as it is to us now, that a single person could have been responsible for changing the outcome of an event watched by some fifty million people. In real life, the 1919 World Series was fixed not by Wolfsheim, but with great skill and audacity by Arnold Rothstein, a Jewish gangster. A young lieutenant colonel in the U.S. Army named Dwight Eisenhower eagerly followed the game as the scores came in via telegram, and like everyone else, never suspected a thing. He would remark years later that the revelation of the conspiracy that had thrown the series produced a profound change in his perspective about the world; it taught him never to trust in first appearances.

This is a book for a world that has come to think like Nick Carraway, riding in disbelief through life on the wake of conspiracies we won’t believe until we see, unable to comprehend why they happen and who makes them happen. This ignorance of how things really work is depressing to me. Because it opens us up to manipulation. It closes us off from opportunities to produce fruitful change and advance our own goals. It is time to grow up.

It is just one word: Conspiracies. What follows is Machiavelli’s guide for rising up against a powerful enemy, for ending the reign of a supposed tyrant, for protecting yourself against those who wish to do you harm. It is appropriate that such a book sits just within arm’s reach of one of Thiel’s wingback armchairs and not far from the chess set which occupies considerable amounts of his time. Something in these pages planted itself deep into Thiel’s mind when he first read it long ago, and something in Thiel allowed him to see past Machiavelli’s deceptive warnings against conspiracies and hear the wily strategist’s true message: that some situations present only one option. It’s the option available to many but pursued by few: intrigue. To strategize, coordinate, and sustain a concerted effort to remove someone from power, to secretly move against an enemy, to do what Machiavelli would say was one of the hardest things to do in the world: to overthrow an existing order and do something new. To engage in a conspiracy to change the world.

Every conspiracy is a story of people. The protagonists of this one are two of the most distinctly unique personalities of their time, Nick Denton and Peter Thiel. Two characters who, not unlike the cowboys in your cliché western, found that the town—whether it was Silicon Valley or New York City or the world’s stage—was not big enough for them to coexist. The gravitational pull of the two figures would bring dozens of other people into their orbit over their ten-year cold war along with the FBI, the First and Fourth Amendments, and soon enough, the president of the United States. It somehow dragged me in, too. In 2016, I would find myself the recipient of unsolicited emails from both Peter Thiel and Nick Denton. Both wanted to talk, both were intrigued to hear I had spoken to the other. Both gave me questions to ask the other. And so for more than a year, I spent hundreds of hours researching, writing about, and speaking to nearly everyone involved. I would read more than twenty thousand pages of legal documents and pore through the history of media, of feuds, of warfare, and of strategy not only to make sense of what happened here, but 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). The result is a different kind of book from my other work, but given this extraordinary story, I had little choice. What follows then are both the facts and the lessons from...

Machiavelli said that a proper conspiracy moves through three distinct phases: the planning, the doing, and the aftermath. Each of these phases requires different skills—from organization to strategic thinking to recruiting, funding, aiming, secrecy, managing public relations, leadership, foresight, and ultimately, knowing when to stop. Most important, a conspiracy requires patience and fortitude, so much patience, as much as it relies on boldness or courage. The question that remains: What would a world without these skills look like? And would a world with more of them be a nightmare or something better? That’s for you to decide. In the meantime and for the record, I simply present what happened.

Mankind has always crucified and burned, a great playwright once said. We take a secret pleasure in the misfortune of our friends, said another wise man. For Gawker it was no secret pleasure but a conspicuous one and to it they added the power of blogging. Nick’s instincts were captured and compounded by the economics of his instruments: twenty-something writers with school debt and little income. Overeducated children of Boomers, the children of parents whose idealism became materialism, the writers believed they had something to say because those same parents had told them they were special and important and talented. Previous generations of writers came to New York City with a dream. This generation came with a bone to pick—for the broken economy, for the collapse of old industries, for the hypocrisy and fakeness that had finally become acute. They wanted a seat at the Algonquin and ended up sharing a bedroom in Bushwick, writing twenty articles a week (nineteen of which no one would read) for $12 apiece. Of course they were pissed. A New York Times writer would later dub this ethos the “rage of the creative underclass.” A Gawker headline captures it better: “It’s OK to Be a Hater Because Everything Is Bad.” The existentialists spoke of ressentiment, or the way that resentment creates frustration which fuels more resentment. Philosophers might have said this feeling was pointless, but they knew it was a fearful force. Gawker would revel in ressentiment, of its writers a...

As Cicero said, the beginnings of all things are small, and so was this one. At its beginning, at the impetus, there was simply something one person thought should be public that another thought was private; that one person thought was funny and that the other believed was serious. I don’t want them to know. It’s not their business. It’s not who I am. It’s not how I want them to see me. He is upset. His boyfriend is upset, upset that he is upset. Thiel’s frenzied mind races now, as it had for others written about by Gawker. The instinct to curl into a ball. The hope that this will go away. The anger at the unfairness of it, the randomness of it, the needless im-politeness of it. The sense that someone was doing this for sport, as part of a game. That someone had this power and wielded it so capriciously . . . It is from these kinds of thoughts that conspiracies are born.

His path was in some ways traditional—Stanford to Stanford Law to judicial clerkship to high-powered law firm—but it was also marked by bouts of rebellion. At Stanford he created and published a radical conservative journal called The Stanford Review, then he wrote a book that railed against multiculturalism and “militant homosexuals” on campus, despite being both gay and foreign born. His friends thought he might become a political pundit. Instead he became a lawyer. Then one day, surprising even himself, he walked out of one of the most prestigious securities law firms in the world, Sullivan & Cromwell, after seven months and three days on the job. Within a few short years, Thiel formed and then sold PayPal, an online payments company, to eBay for $1.5 billion in July 2002, the month that Nick Denton registered the domain for his first site, Gizmodo. With proceeds of some $55 million, Thiel assembled an empire. He retooled a hedge fund called Clarium into a vehicle to make large, counterintuitive bets on global macro trends, seeding it with $10 million of his own money. In 2003, Thiel registered a company called Palantir with the Securities and Exchange Commission. In 2004, he would found it in earnest. The company would take antifraud technology from PayPal and apply it to intelligence gathering—fighting terrorism, predicting crime, providing military insights. It would take money from the venture capital arm of the CIA and soon take on almost every other arm of the gov...

It’s a classic collective action problem: we know things are bad, but they only affect each of us a little bit. So who is going to take care of it for us? Plenty of people believe in the theory of so-called great men of history, but who believes I am that great man? There is ego in that, silliness even. The economist Tyler Cowen once observed that at some point in the 1970s, Americans went from being the country that took literal moonshots to being the people who waited patiently in long lines for gasoline. It’s not completely accurate, of course, but it is a criticism that resonates with Thiel as he sits in his office at the Presidio one day looking at the Golden Gate Bridge and wonders if people will ever build something like that again. Do people even have the arrogance anymore? To test the limits? To try big things?

“When personal gossip attains the dignity of print, and crowds the space available for matters of real interest to the community,” future Supreme Court justice Louis Brandeis wrote in the Harvard Law Review in 1890, in a piece which formed the basis for what we now know as the “right to privacy,” it “destroys at once robustness of thought and delicacy of feeling. No enthusiasm can flourish, no generous impulse can survive under its blighting influence.” Brandeis’s words reflected some of the darkness of Kierkegaard’s worries from fifty years earlier and foretold some of that sullying paranoia that was still to come fifty years in the future. Thiel had read this article at Stanford. Many law students do. Most regard it as another piece of the puzzle that makes up American constitutional legal theory. But Peter believed it. He venerated privacy, in creating space for weirdos and the politically incorrect to do what they do. Because he believed that’s where progress came from. Imagine for a second that you’re the kind of deranged individual who starts companies. You’ve created cryptocurrencies designed to replace the U.S. monetary system that somehow turned into a business that helps people sell Beanie Babies and laser pointers over the internet and ends up being worth billions of dollars. Where others saw science fiction, you’ve always seen opportunities—for real, legitimate business. You’re the kind of person who is a libertarian before that word had any kind of social resp...

First, a slight of some kind, which grows into a larger dissatisfaction with the status quo. A sense that things should be different, and will be different, except for the worse, if something doesn’t change. But then comes a second step, a weighing of the stakes. What if I do something about this? What might happen? What might happen if I do nothing? Which is riskier: to act or to ignore? History is uncertain on this question, as were the people in Peter’s life, the ones trying to tell him that there wasn’t much that could be done. Peter would, at one point, pass me a copy of The Fifteen Decisive Battles of the World by Sir Edward Shepherd Creasy, the book he had read as he’d mulled his options over. The epigraph to the chapter on the Battle of Valmy quotes Shakespeare: A little fire is quickly trodden out, Which, being suffered, rivers cannot quench.

Twenty-five hundred years ago, Thucydides would say that the three strongest motives for men were “fear, honor, and self-interest.” Fear. Honor. Self-interest. All covered. Which is the truest of them for Thiel? Does it matter? Someone had begun to think seriously that something needed to be done and believed that he might be the person to do it.

One of the most profound intellectual influences on Peter Thiel is a French thinker named René Girard, whom he met while at Stanford and whose funeral he would eventually speak at in 2015. Girard’s theory of mimetic desire holds that people have no idea what they want, or what they value, so they are drawn to what other people want. They want what other people have. They covet. It’s this, Girard says, that is the source of almost all the conflict in the world. Is this not the source of the tension between Denton and Thiel, not because they are so different, but because they are so similar? Still there is a chasm between them, the power differential that put one in position to out the other. Growing into his role as a maverick publisher, Nick Denton had through the years developed the confidence of a journalistic gangster, a man who didn’t just flirt with the edge, he got married and built an impressive home there. Perhaps he hadn’t made as much money as Thiel, but his profile and his impact were more immediately and culturally recognized. Perhaps he assumed that Thiel felt powerful and would brush the attacks off. More likely, perhaps Denton assumed that Thiel would recognize that this was the game. That this was a tax on successful, rich people—being mocked and teased online. Or perhaps it was simply the traditional arc of the bully who becomes empowered the more he picks on others, grows to like the feeling it creates, and the longer he goes unchallenged, the more he com...

It is always revealing to see how a person responds to those situations where he’s told: “There’s nothing you can do about it. This is the way of the world.” Peter Thiel’s friend, the mathematician and economist Eric Weinstein, has a category of individual he defines as a “high-agency person.” How do you respond when told something is impossible? Is that the end of the conversation or the start of one? What’s the reaction to being told you can’t—that no one can? One type accepts it, wallows in it even. The other questions it, fights it, rejects it. This choice defines us. Puts us at a crossroads with ourselves and what we think about the kind of person we are. “Anyone who is threatened and is forced by necessity either to act or to suffer,” writes Machiavelli, “becomes a very dangerous man to the prince.” And Peter Thiel was driven into a desperate position, of and not of his own making, that had started with a matter of his identity and become about a deeper identity. Now he had not only decided to act against Gawker, but he would conspire to destroy them.

Machiavelli writes that a conspiracy without any coconspirators is not a conspiracy. It’s just a crime. This is also basic legal principle. If you kill someone by yourself, in the heat of the moment, it’s murder. If you meticulously plan it with someone else beforehand, that’s conspiracy. Lee Harvey Oswald almost certainly assassinated John F. Kennedy by himself. What he hoped would happen as a result is unclear. John Wilkes Booth conspired not only to assassinate Abraham Lincoln, but working with Lewis Powell and George Atzerodt also aimed to assassinate Andrew Johnson and William Seward. It was a coordinated attempt by Confederate sympathizers to usurp the United States government. It’s not simply a single crime, but a crazed, desperate effort to turn back the tide of a lost war. In his definitive book on the subject of strategy, Lawrence Freedman writes that “combining with others often constitutes the most strategic move.” By definition, the first move in the act of a conspiracy is the assemblage of allies and operators: your coconspirators. Someone to do your bidding, to work with you, someone you can trust, who agrees with you that there’s a problem, or is willing to be paid to agree with the sentiment that it’s about time someone, somebody did something about this. Each hand doesn’t need to know what the other is doing, but there needs to be more than one set. Thus, Thiel’s vague idea to do something about Gawker is concretized into conspiracy on April 6, 2011. It b...

There is a scene in the movie The Assassination of Jesse James by the Coward Robert Ford. At the beginning, in the woods, Robert Ford, played by Casey Affleck, illustrates this phenomenon. He thinks the outlaw Jesse James is a great man. He thinks that he, himself, is a great man, too. He wants someone to recognize that in him. He wants someone to give him an opportunity—a project through which he can prove his worth. It just happens that Frank James would size the delusional, awkward boy up in the woods outside Blue Cut, Missouri: “You don’t have the ingredients, son.” In contrast, Mr. A is ambitious, but it’s paired with self-confidence, social adeptness, and a clear sense of what Thiel wanted. Even so, the prospect of meeting with Thiel is intimidating: his stomach churning, every nerve and synapse alive and flowing. He’s twenty-six years old. He’s sitting down for a one-on-one evening with a man worth, by 2011, some $1.5 billion and who owns a significant chunk of the biggest social network in the world, on whose board of directors he also sits. Even if Thiel were just an ordinary investor, dinner with him would make anyone nervous. One quickly finds that he is a man notoriously averse to small talk, or what a friend once deemed “casual bar talk.” Even the most perfunctory comment to Thiel can elicit long, deep pauses of consideration in response—so long you wonder if you’ve said something monumentally stupid. The tiny assumptions that grease the wheels of conversation...

But that’s the nice thing about lawyers: as long as you’re paying them, they’re usually good with whatever terms go along with it. Compartmentalization is their job. It’s how they represent people who are guilty, how they file long motions they know are unlikely to be successful, how they can patiently keep secrets that they’d otherwise love to be able to share. Harder was nearly twenty years into his legal career when he was first approached. Though he often worked on celebrity cases they tended to be for routine matters, not exciting criminal proceedings or blockbuster cases, and when you’re retained to enforce rights of privacy and publicity on behalf of your clients, it tends to follow that they don’t want you grandstanding in the media on their behalf, building a profile as you work for them. His last appearance in the New York Times had been in 2001, about a case for a client who had been let go from an ad firm almost immediately after she left her new job to join it. Harder won two months’ back pay. It’s not exactly the kind of victory that marked the career of lawyers like Marty Singer, whom Harder had once worked for, and whom the Times had called the “Guard Dog to the Stars.” A lawyer who had publicly fought cases over celebrity sex tapes, who tangled with Gawker once on behalf of Rebecca Gayheart and the actor Eric Dane when their tape had run on Gawker and managed to eke out a small settlement, without an admission of guilt. So why not hire Singer? Because Pete...

A start-up is, in Peter’s definition, “a small group of people that you’ve convinced of a truth that nobody else believes in.” This is a fitting definition of what has assembled here as well. More people would be added as time passed. Allies and enemies of enemies would be brought into the fold. But all of it would proceed from the shared belief of these three men that the destruction of Gawker might be possible. Now they had their first decision to make together: how.

“With patience and resources,” Mr. A would come to say often on his weekly calls with Peter, “we can do almost anything.” Tolstoy had a motto for Field Marshal Mikhail Kutuzov in War and Peace—“Patience and Time.” “There is nothing stronger than those two,” he said, “. . . they will do it all.” In 1812 and in real life, Kutuzov gave Napoleon an abject lesson in the truth of that during a long Russian winter. The target, Nick Denton, is not a patient man. Most entrepreneurs aren’t. Most powerful people are not. One of his editors would say of Denton’s approach to stories, “Nick is very much of the mind that you do it now. And the emphasis is to get it out there and be correct as you can, but don’t let that stand in the way of getting the story out there.” Editorially, Nick Denton wanted to be first—which is a form of power in itself. But this isn’t how Thiel thinks. He would say his favorite chess player was José Raúl Capablanca, and remind himself of the man’s famous dictum: To begin you must study the end. You don’t want to be the first to act, you want to be the last man standing. History is littered with examples of those who acted rashly in pursuit of their goals, who plunged ahead without much in the way of a plan, and suffered as a result. One could argue that the bigger of Nixon’s two blunders wasn’t his attacks on the Democratic Party but the decision to go after Katharine Graham and the media, and yet both decisions were the product of a fundamental lack of patien...

Peter tells me, echoing the thrust of Mr. A’s pitch to him in Berlin the previous April, “but I wanted to find a cause of action that wasn’t libel.” Harder agrees; legally it’s the strategically wise move, so they decide to avoid cases related to libel or defamation. Libel and defamation cases are notoriously hard to win in the American legal system. They are fraught with First Amendment complications where the bias is always toward the publisher and the burden of proof on the claimant—especially if he or she satisfies the “public figure” standard—is overwhelming. A private citizen has to prove only negligence on the part of the publisher. A public figure has to prove “actual malice”—that the publisher either knew beforehand that its statements were false or acted with “reckless disregard” as to the truth of the published statements. This was the issue that rendered fruitless so many of Peter’s encounters with sympathetic ears in the years after his initial outing.

“The gating resource here was not capital,” Thiel said. “The gating resource was the ideas and the people and executing it well. It’s not like lawsuits haven’t been brought in the past. It’s something that’s been done, so we were required to think very creatively about this space, what kind of lawsuit to bring.” Most of the ideas do not stand up to scrutiny, or to Thiel’s ambitions. A slap on the wrist from the FCC about affiliate commissions will accomplish little. Exploiting the financial misdeeds of the company would likely require an inside man, and this would be nasty, deceitful business. It wasn’t just a question of which strategy might actually win, it was also figuring out which one could actually do real damage. “It was important for us to win cases,” Thiel said. “We had to win. We had to get a large judgment. We did not want to bring meritless cases. We wanted to bring cases that were very strong. It was a very narrow set of context in which you could do that. You did not want to involve political speech, you did not want to involve anything that had anything remotely connected to the public interest. Ideally, our cases would not even involve the First Amendment at all.” The First Amendment was unappealing not because Thiel is a libertarian, though he is, but because as a strategist he understood that it was Gawker’s strongest and most entrenched position: we’re allowed to say anything we want. It challenges the legal system and conventional wisdom where they are...

Their suspicions are confirmed when they read a public memo from Denton to his staff in mid-2010 that says, “The staples of old yellow journalism are the staples of the new yellow journalism: sex; crime; and even better, sex crime.” And, as Nick would tell The Atlantic, looking back on some of his sites’ earlier posts, his regrets came not from publishing these types of stories, but from bothering to defend them when criticized. “We should have just said our interest was voyeuristic. ‘We did this story because we thought you would like it. We thought it was funny, so we thought you would think it was funny too.’ And there was a tidal wave of traffic and attention.” Printouts of these stories came to Mr. A and he would brief Thiel on the worst of them. “The more I studied the organization, the harder it was to find good,” Mr. A explained. It was obvious, too, that this process was accelerating, which was not exactly a bad thing if you were sitting on the outside looking for a weakness that could be exploited, or hoping for your enemy to make a fatal mistake. More posts being written, more writers being hired, Gawker’s swagger and sense of untouchability growing. It was almost a matter of fact that this could not continue without eventually causing serious trouble. A Gawker writer once explained why he liked working at Gawker, what drew him there: “Ultimately, I would rather work at a place that’s bold enough to fuck up than one that is too afraid to ever risk it.” This is a...

But Thiel now believes that Gawker’s impression of its own strength is based on the quirks of past events and not the fact of law. This belief is an edge, hardly a black one, but a real edge nonetheless. And he’s going to test it. “Given the same amount of intelligence, timidity will do one thousand times more damage in war than audacity” is the dictum from Clausewitz. The reverse is true as well. It’s Thiel’s investment strategy: with the right conditions, a little boldness will make much more progress than timidity will ever protect. So here Thiel finds his first edge: a willingness to try. To prove something in the court of law, to a jury.

To recoil at this thought is natural. While Machiavelli never said—as some might claim—that we must lose that part of ourselves altogether in the pursuit of power, he did say that for the prince who wishes to remake the world to his liking, the natural impulse to be kind, forgiving, and empathetic must temporarily be suppressed. This is not an easy thing to do, even in the face of overwhelming necessity. By 1939, Franz Halder, a German general, had taken to carrying a pistol so that when he was in the room with Hitler, he might assassinate him. But he could never pull the trigger. He could not reconcile how he could take up as “human being and a Christian to shoot down an unarmed man.” In fact, many German generals knew that someone should do it, they wanted it to have been done, but they could not do it themselves . . . because it was unethical. Hans Oster, himself a dogged German conspirator against Hitler, would despair, “We have no one who will throw the bomb in order to liberate our generals from their scruples.” Every conspiracy is the story of man sketching out a plan on paper, committing to something in a secret meeting room, and then there is the and then. The man believes he has considered any and all reservations, but only when it looks and feels like it will actually happen—when he stands in the same room with the enemy, forced to really do the deed that had been only

The Count of Monte Cristo would put it better: “What a fool I was not to tear my heart out on the day when I resolved to avenge myself!” Ah, but what dangerous business this is. This artificial hardening is a dangerous crossroads, a bargain with our primal forces that not everyone escapes or can emerge from with clean hands. William James knew that every man is “ready to be savage in some cause.” The distinction, he said, between good people and bad people is “the choice of the cause.”

This is the nature of the American legal system, and of conspiracy as well. It’s slow, adversarial. Moral quandaries and personal issues are reduced to brief moments and decided on small points of law. Even a winning case will likely see as many setbacks as it does victories, and it falls upon the constitution of the players to weather the former to get to the latter. And this isn’t even the real legal battle—these are just arguments over the attempts to obtain what is called “prior restraint” of speech. The conspirators were trying to get the tape taken down before—until—they’d won their case. Harder’s thinking was that a sex tape recorded without consent was so egregious that a judge would be sympathetic. Gawker’s lawyers enjoy disabusing their opponent of this notion. So does the judge.

The essayist and investor Paul Graham, a peer and rival of Peter Thiel’s, has charted the trajectory of a start-up, with all its ups and downs. After the initial bump of media attention, the rush of excitement from the unexpected success, Graham says that the founders enter a phase where the novelty begins to wear off, and they quickly descend from their early euphoria into what he calls the “trough of sorrow.” A start-up launches with its investments, gets a few press hits, and then smacks right into reality. Many companies never make it out of this ditch. “The problem with the Silicon Valley,” as Jim Barksdale, the former CEO and president of Netscape, once put it, “is that we tend to confuse a clear view with a short distance.” Here, too, like the founders of a start-up, the conspirators have smacked into reality. The reality of the legal system. The defensive bulwark of the First Amendment. The reality of the odds. They have discovered the difference between a good plan and how far they’ll need to travel to fulfill it. They have trouble even serving Denton with papers. Harder has to request a 120-day extension just to wrap his head around Gawker’s financial and corporate structure. This is going to be harder than they thought. It always is. To say that in 2013 all the rush and excitement present on those courthouse steps several months earlier had dissipated would be a preposterous understatement. If a conspiracy, by its inherent desperation and disadvantaged position,...

By the time of their second string of setbacks in 2013, Peter Thiel was already six-odd years into this dance with Gawker. Mr. A was two years in. Harder himself was nearly a year in. It was well into the end of its beginning and it had not begun well. If there was anything they had to be thankful for, it would be something they could not appreciate until later, and that would be that they were mercifully in the dark about all that remained ahead of them, all three long years of struggle and difficulty that were still to come.

The concealment of intentions is critical to countless worthwhile and perfectly legitimate enterprises, not only in business or defense but also in journalism. In her classic The Journalist and the Murderer, Janet Malcolm wrote, “If everybody put his cards on the table, the game would be over. The journalist must do his work in a kind of deliberately induced state of moral anarchy.”

“The truest way to be deceived is to think oneself more knowing than others” is La Rochefoucauld’s maxim. To Gawker these pleas of financial hardship from Hogan must have read as confirmation of the edge they believed they had—their money, their brinkmanship would be the determining factor. Because it was what they were doing. They wanted to hear his complaints, that he was hurting from it. They were so overconfident, so sure that this suit would come to nothing that they could not even conceive of a scenario in which Harder might have an advantage over them, or might be doing something other than being stupid. And who in their right mind so believes in transparency that they would correct their overconfident opponent’s fatal miscalculation? Yet let us not confuse the need for secrecy with a blanket justification of any type of behavior. The conspirators remained committed and seem to have observed their self-imposed limitation of legal behavior—perhaps out of moral goodness or perhaps simply because they wanted a clean victory. There were plenty of illicit or untoward things they could have done secretly, but to what end? At what cost? “I think there’s always this question,” Thiel would say. “I do think you always want to think about, you know, when this ultimately comes out. Is it defensible? And I think all the things that we did were defensible. And so secrets aren’t necessarily forever. You have to live with it coming out at the end.”

The Russians call this maskirovka—the art of deception and confusion. It is as old as strategy itself. Undermine your enemy, Sun Tzu advised 2,500 years ago. “Subvert him, attack his morale, strike at his economy, corrupt him. Sow internal discord among his leaders; destroy him without fighting him.” Call down the fog of war, he was telling conspirators and generals and swordsmen, let it descend on your opponent until they cannot see what is right before them. Because “all warfare,” Sun Tzu reminds us, “is based on deception.” Not just keeping secrets—that’s the first part, the passive part, a refusal to reveal your true intentions—but active, outwardly focused deceit intended to disorient and weaken the enemy. The long-term strategic drive to a decisive legal action—the hope of taking a case against Gawker to a real jury of normal people outside the Manhattan media bubble—had been set by Peter Thiel early on. By 2012, not only was the ideal case found with which to execute this strategy, but a lawsuit was filed within days of discovery. As the case wound its way through the legal system in 2013, it had seen many setbacks, some expected and others not, but these setbacks were not without their upside. They had, in the end, created a scenario in which the case’s final home in Florida district court might spell a bankruptcy-level event for Gawker Media.

The line attributed to the management guru Peter Drucker is that culture eats strategy. It’s a truism that applies as much to conspiracies as it does to businesses. It doesn’t matter how great your plan is, it doesn’t matter who your people are, if what binds them all together is weak or toxic, so, too, will be the outcome—if you even get that far. But if the ties that bind you together are strong, if you have a sense of purpose and mission, you can withstand great trials. Gawker once had a strong mission, an animating force that brought everyone together in a similar fashion and moved them forward. It was them against the world. It was, as Nietzsche put it, a war of knives against the present age. Hypocrites, liars, petty tyrants, smug assholes—all found themselves in Gawker’s crosshairs when it launched in 2002. A ragtag army of amateur writers found a great equalizer in writing on the internet, in telling unvarnished truths and not giving a damn about the consequences. Denton’s operation channels the energy of the disaffected and the angry. He is paying them relatively little. He is working them hard. He is empowering them—making them arbiters of culture, of acceptability, of cool. They might not be rich, but if they can bring the rich and powerful to their knees with their writing, it might feel like the same thing. Is this enough for loyalty, though? Is this enough to bring them together in adversity?

If Thiel is Melville’s Ahab, manically chasing a white whale wherever it takes him, then Denton is Melville’s Benito Cereno, a prisoner on his own ship, unable to communicate the terror of his position, being driven slowly insane by the sound of the sharpening hatchets of his crew. He can’t sell the company with a lawsuit hanging over it, he can’t settle the case without going back on much of his rhetoric to the writers and in the press. He would try to push the writers to be nicer, to ask them when they would be gratuitously mean or reckless, “What’s your purpose here? What are you hoping to do with this post?” He thought he could manage the energy. He tried new editors, wrote long memos, held long meetings about his editorial vision. But the incentives were built into the core of the company. The writers had no stake in the business, only in the notoriety. They were measured in page views, and they knew the best way to get them was to say and do the things that no one else could—or would. And yet Denton also knew that he could not afford for them to be too much nicer anyway. He needed the traffic to show the growth to lure in new investors to pay the legal bills he was now drowning in. He needed to keep the audience entertained, too. They were fickle, they did not appreciate his predicament. They have their own problems, and don’t care about his.

where was Heather Dietrick in all this? Wasn’t she supposed to be part of the adult supervision—not one of the untrained puppies but a leader? In 2013 she had joined Gawker as its chief counsel. She hadn’t been there when the article was published. Since 2014 she had been the company’s president. Yet she has not convinced her boss, or her coworkers, that this lawsuit is unlike the other cases they have faced, that Hogan is going to go all the way. (She had been told this directly, after all.) Or perhaps she has fallen in with the hard-line faction, too—leaving Nick without the perspective and the advice he so desperately needed. Still united in principle, in common cause against an evil enemy, Peter’s side is not without its problems. It, too, could have been torn apart by its own contradictions and systemic issues. Rich donors are notoriously easy marks. They fund boondoggles as often as they fund the efficient, ruthless machines that people fear are running the world. It’s a real-life luxury tax. Limitless resources are corruptive. They make people lazy. Take Mr. A. In 2011, Thiel’s net worth was roughly $1.5 billion, and conservatively the interest on a billion dollars is hundreds of thousands of dollars a day. Having hooked Peter’s interest in the project, finagling himself into a role as the man on the ground, essentially anything he could have asked for would have been his, had he run back the playbook he used in Berlin. Instead of asking to be paid from the beginnin...

Hofstadter’s Law,

There is a story about a young John D. Rockefeller who found himself stuck with bullying, corrupt business partners. He wants to break with them, but he can’t, because they control the votes. They are squeezing his business to death. They abuse him, talk about forcing him out. What is he to do? Quietly, Rockefeller lines up financing from another oilman and waits. Finally there is a confrontation; one of them tries to threaten him: “You really want to break it up?” Yes. He calls their bluff. They go along, knowing that the firm’s assets will have to go to auction. They’re sure they’ll win—Rockefeller doesn’t have that kind of money. He bids, they bid, he bids, they bid. Rockefeller wins the auction. A few weeks later, the newspapers announce his new partnership—revealing who had backed his bid—and the news that Rockefeller is, at twenty-five, an owner of one of the largest refineries in the world. On that day his partners “woke up and saw for the first time that my mind had not been idle while they were talking so big and loud,” he would say later. They were shocked. They’d seen their empire dismantled and taken from them by the young man they had dismissed. Rockefeller had wanted it more. The story of this conspiracy, too, is the story of one person working while the other talked big and loud. One side confident in its power and the self-evident inarguability of its position—believing until the very moment of the trial that it would likely be tossed out, that even if it w...

Heather Dietrick would explain beliefs about the jury to reporters at the time: “I think as a common-sense matter, they’re going to see that, see what he’s talked about in the past,” she would say. “He’s talked about really, really graphic details of his sex life, again and again and again, including on the shock jock’s show. These are practical people. I think they’re going to see through him and say, ‘Give me a break. Take responsibility for what you did here.’” Oh, Heather. How could you? She should have been telling her boss to settle, rectifying before it was too late the error Denton and the legal department had made in not seeing Hogan’s perspective “as a human being” when that cease and desist first came in. Instead she was needling the victim in the media. She was lying to herself and to the people who worked at Gawker. She had it all wrong. “The external positioning for a year and a half leading up to trial,” Thiel says of Gawker, “was that Hogan’s case was terrible, and if he won it would be a small amount that would get reversed on appeal. If you have a propaganda line that you keep telling people, there’s some point at which you have to start believing it.”

The great sin for a leader, Frederick the Great once observed, was not in being defeated but in being surprised. How did Denton not see this? How did Gawker’s chief strategy officer not see that this was a fight they could not win? Where was their publicist? Heather Dietrick, the one they had chosen to sit in the courtroom for them, who had been privy to every part of this case from the beginning—where had she been? Denton would say in retrospect that Gawker’s “audience share in Williamsburg was not decisive.” It didn’t matter what his friends in Manhattan or his readers in Brooklyn thought of the trial, what mattered was what the jurors thought. What mattered was whether they believed Hogan on the stand. “Hogan used language—and the trust his brand engendered—to make his own reality,” Denton said, intellectualizing his own decimation. “We were reminded that he had many more followers than Gawker did—both in the jury and in the general population.” “PR can be powerful, it can be effective, but it can always backfire when you start to believe it too much. They needed to say they were sorry. If they had done that, they would’ve survived. Instead, they insisted on the right to be evil,” Thiel explained. The word “sociopathic” has been used on occasion to describe Gawker, but even sociopaths are generally better at judging situations, at reading people, at extrapolating how things are likely to go, than anyone associated with the Gawker team seemed to be in this moment.

On the day of the verdict, the New York Times editorial section would publish a debate of experts, asking about the implications of the case. Two of the three experts would come down against Gawker and for Hulk Hogan, underscoring Thiel’s early goal to predicate the dispute on privacy, not press freedom. One, a law professor and former journalist, wrote, “When human dignity is degraded by depictions of sex, nudity or medical conditions the ‘journalism’ should not be called newsworthy.” The next day the former assistant general counsel of the New York Times would be quoted in another piece published in the paper: “I think the damages are crazy, but I just don’t see this as a terrible blow to the First Amendment.” The dean of the law school at UC Irvine would follow in the same story: “I think this case establishes a very limited proposition: It is an invasion of privacy to make publicly available a tape of a person having sex without that person’s consent. I don’t think it goes any further than that and I do not see a First Amendment basis for claiming that there is a right to do this.” What had begun as a petty squabble between two similar, strange men had become something bigger, a chance to draw the line about what was allowed in the public sphere. Thiel had set out to destroy this thing that he thought was destroying an important part of society, of culture. There was revenge in this, too, absolutely. Nick Denton had said, “Peter Thiel makes me sick,” and the feeling wa...

Machiavelli warns conspirators that the most dangerous time is after the deed is done. It is as if Peter and Harder did not fully consider this. “We thought the point of maximum tension would be the trial and once we were done with that, you know, if they couldn’t figure it out at the trial they never would,” Peter says. He would also say that he thought the end of the trial would put them past the “point of maximum danger.” In fact, this was exactly the point of the highest vulnerability. Loss inherently makes the loser sympathetic. We can easily be made to feel bad for the person on the other side of a true catastrophe, even if just minutes before we thought they had it coming to them.

Thiel knew the importance of finishing. He had written it in Zero to One. “It is much better to be the last mover,” not the first mover. “Grandmaster José Raúl Capablanca”—Thiel’s favorite chess player—“put it well: to succeed ‘you must study the endgame before everything else.’” The conspirators had studied it, but only so far as their maneuvering took to get the other man’s king on its side. What they failed to consider was that in any chess match between masters, there is always more than one game. Each requires its own unique plan.

“I’m not a fighter, I’m a waiter” is how Walter Winchell opens his memoir, addressing the enemies who had prematurely ended his career and toppled him from power. “I wait until I catch an ingrate with his fly open, then I take a picture of it.” The gossip columnist Louella Parsons, driven from relevance by studio heads tired of her tyranny, dragged down by lawsuits at the end of her life, would retreat into literal silence in protest. The last ten years of her life, it was claimed she never said another word. Which would it be? What would be Denton’s path?

The historian E. P. Thompson said that history never happens as the actors suspect, that history is instead the “record of unintended consequences.” The assassination of Julius Caesar does not restore the Roman Republic, it leads to a brutal civil war and, at the end, another emperor. The Allied powers destroy Hitler and Germany but empower Russia and Stalin and create a new Cold War to follow the conclusion of the hot one. There is always something you didn’t expect, always some second- or third-order consequence. Peter Thiel’s conspiracy had achieved its intended outcome. A negotiated peace had been found. Gawker.com would cease to publish. A new leader was in charge of the rest of the sites, some of the offending articles would be removed. But what would the consequences, intended and otherwise, of it all be? What had this brilliant, independent mind neglected to see? What, if anything, would come as a surprise? His own power and strength for one.

In the years he conspired against Gawker, Thiel would come to see the U.S. legal system differently. He later said that, before the case against Gawker, he had believed that the problem in America was too many lawsuits and too many lawyers. Like many media outlets, Gawker’s legal strategy had been to lean into that understanding—to be the black hole of time and money whose event horizon no one could afford to confront. With his immense resources, Thiel believed he had simply changed the equation. The fact that Hulk Hogan, a “single-digit millionaire” as Thiel put it, would not otherwise have had the funds to pursue a case like this means that there might be many other legitimate legal precedents or cases that have otherwise gone unpursued out of intimidation or lack of funds (it cannot be said with a straight face that A.J. and Nick did not have “legal protection”). Having actually gone through the system, Thiel would come to believe that maybe there weren’t enough lawsuits. That people should try more. And so he puts more money behind the idea, funding in 2016 a start-up called Legalist, conceived by a Thiel fellow, dedicated to bankrolling lawsuits with a high probability of winning and possibly setting new precedents.

Peter thought he’d be greeted as a liberator, that Gawker was a scourge that once eliminated would allow for open, collaborative discussion. If anything, the opposite has happened. The candidate he helped put in office embodies many of the bullying traits that Thiel claimed to abhor. Trump would also 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, perhaps in the quiet cabin of his Gulfstream, that the man in the White House is essentially the opposite of everything he had spent his life believing in, that Trump threatened the very libertarian freedoms and open civil discourse that Thiel had spent his money protecting. To know he is associated with that, in certain ways responsible for it, might be the most unintended consequence of all.

In Maui, where Thiel has a home and spends a good deal of his time, officials once introduced a species of mongoose to kill rats. Only after introducing them did it occur to anyone that rats are nocturnal and mongooses are diurnal. A bad problem became worse, a rat problem became a mongoose problem. You launch a conspiracy to protect your privacy and make yourself famous. You seek to rid the world of a bully and you find yourself with Trump. The nihilists on the left are sent in a diaspora from Gawker to other media outlets, matched tit for tat by the nihilists on the right. And most of them hate you. The CIA coined a term to describe this: blowback. The word was first used in print in 1954 . . . and the next fifty years would vividly paint its tableau. Teaching a generation about why you don’t intervene, why you don’t get involved. Because the end of a conspiracy can be not unlike the beginning of it: an intolerable status quo. Perhaps even for the same people. But Thiel knew this going in. He had read that Shakespeare line about fires trodden out and figured that it was still worth the risk.

Once one forges oneself into a hammer of justice and feels the power of crushing one’s enemies, driving them before one and taking their possessions as one’s own, does one become addicted to it? It can become a cycle without end. It can change you, ruin you. One of the worst things that can ever happen to a leader is to unconsciously associate resistance and criticism with opportunity. When everyone tells you you’re wrong and you turn out to be right, you learn a dangerous lesson: Never listen to warnings. And so the reason that few conspiracies are followed by additional successful conspiracies is because of this process and the changes that power produces.

Lyndon Johnson would famously conspire to steal a Senate election from Coke Stevenson in 1948, which put him on the path to the presidency. But given how it went, and the fact that Coke died an old man, surrounded by people who loved and admired him, who is to say that LBJ really won? Perhaps the most interesting unintended consequences, however, were the obvious ones. The ones that no one seriously thought could happen. First, the sex tape actually disappeared. Try to find it—I dare you. You can’t. The Streisand Effect now has at least one exception. Trying doesn’t always backfire.

He would end this story at the place so well captured at the end of one of his favorite novels, Arthur C. Clarke’s The City and the Stars: “There is a special sadness in achievement, in the knowledge that a longdesired goal has been attained at last, and that life must now be shaped towards new ends.”

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. How we have lost this. How squeamish we have become. We now blindly demonize what is often one of the most effective forms of action. How vulnerable this ignorance has made us to the few real conspiracies, successful or not, that exist in the world. In this rare occasion, though, we got a glimpse, a peek behind the curtain, as the title of Gawker’s last post put it, of how things work. Now we know. Peter showed us. And yet our instinct is to turn away, to put our fingers in our ears. It’s why not once in nearly a decade of concentrated effort and scheming directed at a single enemy—at an entity who was obsessively covered and followed by the media—by an opponent who publicly stated his undying hatred of that enemy, did a single spectator, victim, or even many of the participants suspect any of what you read in the pages of this book. There is no question that what Thiel did over those years was brilliant, cunning, and ruthless. It is equally true that Gawker mostly beat itself. Denton and company allowed this to happen. Even the most cynical and aggressive media site on the pla...