Conspiracy, page 1
Portfolio/Penguin
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Copyright © 2018 by Ryan Holiday
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ISBN: 9780735217645 (hardcover)
ISBN: 9780735217669 (eBook)
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To all those who are conspiring, and all those who deserve to be conspired against . . .
Contents
Title Page
Copyright
Dedication
Epigraph
A Word
Introduction
Part I: The Planning
1. The Inciting Incident
2. Deciding to Act
3. Turning to Conspiracy
4. Assembling the Team
5. Finding the Back Door
6. Tear Out Your Heart
7. Seizing the Sword
Part II: The Doing
8. Prepare for Setbacks
9. Know Thy Enemy
10. The Power of Secrets
11. Sow Confusion and Disorder
12. The Ties That Bind
13. The Testing of Faith
14. Who Wants It More?
Part III: The Aftermath
15. The Battle for Hearts and Minds
16. Managing the Aftermath
17. The Art of Settling
18. There Are Always Unintended Consequences
Conclusion
Acknowledgments and a Note on Sources
Sources
More From Me
About the Author
I couldn’t stand it. I still can’t stand it. I can’t stand the way things are. I cannot tolerate this age. What is more, I won’t. That was my discovery: that I didn’t have to.
—Walker Percy, Lancelot
A Word
This is the story of a conspiracy, the story of a billionaire who set out to make an example of a millionaire, to destroy the man’s life’s work in response to a cruel transgression made as thoughtlessly as it was quickly forgotten. It is a story of poetic justice on a grand scale, plotted silently for nearly a decade. It is also a book about that controversial word and method—conspiracy—which has long terrified and intrigued.
There is an unpleasantness in talking about conspiracies, I’ll grant that. Yet conspiracy is a neutral word. It depends on what one does with it. Our tendency to shy away from this truth creates a profound ignorance of how things really work, and what it means to be strategic, to be powerful, and to try to shape events rather than simply be shaped by them.
So what then do we mean when we talk about this word? Certainly not imaginative guesses about what goes on in the shadows, or silly theories. Conspiracy entails determined, coordinated action, done in secret—always in secret—that aims to disrupt the status quo or accomplish some aim.
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.
Nearly a century has passed, and too many of us have not yet lost that Jazz Age naïveté. One longtime Washington columnist wrote recently that years of covering politics taught him one lesson: the legend of Washington as a ceaseless, ruthless, scheming place is simply that, a legend. The truth, he says, is that “No one can carry out complicated plans. All parties and groups are fractious and bumbling.” We nod our heads in agreement. We shake our heads in disappointment.
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.
Nick Denton, whom you will come to know in these pages, is a kind of freethinker who has always held that the things other people are afraid to say are precisely the ones that need saying most. Peter Thiel, whom you will also come to know, has famously become associated with one question, which he uses in interviews and over long dinners: “What important truth do very few people agree with you on?”
I’ll give you mine to close this short preface: Perhaps we have too few conspiracies, not too many. Too little scheming, rather than too much. What would happen if more people took up plotting, coordinating how to eliminate what they believe are negative forces and obstacles, and tried to wield power in an attempt to change the world? We could almost always use more boldness, and less complacency. We could use less telegraphing of our intentions or ambitions and see what secrecy, patience, and planning might accomplish. We could use a little more craziness and disruption, even from the people we disagree with.
This book is my homage to that complicated idea, told in part through the complicated story of one almost unbelievable conspiratorial act.
Please use it wisely.
Introduction
There are no grand, towering bookcases befitting a billionaire in the New York City apartment of Peter Thiel, yet the space is defined by books. They lie in neatly arranged stacks of different heights on nearly every table. Colorful paperbacks and ancient hardcovers about economics, chess, history, and politics fill sets of small, modern shelves in the corners and against the walls.
If you look closely, on the shelf closest to the chef’s kitchen and the arched windows that look out over Union Square Park, there is a small white-spined edition of a book by a sixteenth-century political theorist and Florentine diplomat, worn from use. It is not The Prince, which many people—rich and ordinary alike—pretend to have read, though it is by the same author, Niccolò Machiavelli. This more obscure volume consists of 142 chapters of five-hundred-year-old musings and analysis on the works of a Roman historian two thousand years deceased. Even the title is boring: Discourses on Livy.
Indeed, most of the pages in that book don’t matter for this story. Flip past them for now, you can read them another time. But there, buried between notes on how hereditary rulers lose their kingdoms and the effect of noises upon troops in battle, the title of chapter VI in book III stands out refreshingly in its simplicity.
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.
A thousand miles and a few months away, in a Pinellas County courtroom, just such a conspiracy is reaching its climax. A six-person jury delivers its verdict as a towering professional wrestler named Terry Bollea sits in nervous anticipation. When they announce the judgment, Bollea nearly collapses. He clutches his attorney, Charles Harder, who not long before was an ordinary if not obscure entertainment lawyer. In that moment, they both absorb the enormity of the numbers being entered into the record.
At Thiel’s prompting, and with his backing, the pair had sued Gawker Media, a New York–based gossip and entertainment empire, along with its founder, Nick Denton, and former editor in chief, A. J. Daulerio, for a handful of claims including invasion of privacy, intentional infliction of emotional distress, and violation of Florida’s Security of Communications Act. Four years previously, Gawker.com published excerpts of a secretly recorded tape of Bollea, known to t
Thousands of miles across the Pacific, unknown to the public, or even to many of the conspirators, the twenty-something operative who helped engineer this moment watches the verdict on a livestream. Farther away still is Peter Thiel, asleep in his hotel suite in Hong Kong. Peter is alone, as he often is, and it’s early in China, but he will take a call from this number at any time. It takes twenty minutes to finally get a connection. The cell reception is terrible. “Did you hear?” No, no, he had not. No one expected a verdict this soon, but neither man is staggered. They had been confident of victory for some time, having already experienced this moment, twice, in expensive mock jury proceedings. All that remained to be decided, as far as Thiel was concerned, was how much it was going to cost Gawker. The final tally? $115 million—$60 million of it for emotional distress.
It is perhaps the largest verdict against a publisher in history and the death blow in a feud that began a decade earlier, bringing with it the culmination of a conspiracy that had run nearly as long. A Florida jury has been used to send a message, used to right a perceived wrong that almost everyone else had forgotten. The message was delivered and now Gawker Media, long considered the invincible renegade internet powerhouse, is left bleeding out on the courtroom floor.
The mortal blow is struck. Billionaire tech investor Peter Thiel has struck it.
It is 2016 and he has shocked the world by doing so. Which is what brought me here, to Thiel’s apartment for dinner, in a year in which even the pope has come out to denounce irresponsible journalism as a form of terrorism. I can see the copy of Discourses over his right shoulder as he describes his personal war against Gawker in defense of a right he believes it threatened—privacy—and for what that privacy offers—the space to be peculiar, to think for oneself and to live as one wishes. The chef brings the first, second, and third courses as Thiel talks, revealing a painstakingly organized plot—the plan to reassert agency over a situation many believed was unchangeable, to protect something that most of his Silicon Valley peers had written off as an anachronism, but also to destroy an enemy and make the world a little bit closer to his vision of what it should be.
Twenty blocks downtown there is an equally nice apartment belonging to Nick Denton, the former owner of Gawker Media, the former dark prince of the internet himself. Only, this apartment is almost devoid of furniture. It was empty of its owner until very recently, while the courts decided whether he would be forced to sell it in bankruptcy. No man will take your coat at the door and there is no private chef. Nick will open the door himself and he’ll make you a drink at his SodaStream.
He is much friendlier and more thoughtful than you would assume for a man who created what was one of the most explosive and rebellious media outlets ever. One that, as it spun out of control, growing bigger and bolder, even he privately began to worry might lead to a suicide. As so many reactionary organizations tend to do, it had begun to drift toward absolutism and nihilism.
A quick scan of Denton’s darkly lit apartment confirms that books define it, too. They are built into the architecture itself, lining each window, inset and running up to the thirteen-foot ceilings. Again, one book catches the eye. It’s a copy of the works of the Stoic philosopher Seneca, and it’s there precisely because of the conspiracy Peter Thiel had led against its possessor. Seneca is the author you read when your life’s work has been destroyed, as Denton’s undeniably has. Over the last few years, he has gone from owning one of the most valuable independent websites in the world to being on the wrong side of a $140 million judgment.* He found himself outmaneuvered and outspent by a nemesis he’d deliberately prodded and provoked. It would be now that Denton is looking for the kind of solace needed when your fortunes change, when your seemingly unassailable dominance is suddenly threatened, when you are given an abject lesson in the exercise of power in its most unforgiving form.
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 this conflict—an extended meditation on what it means to successfully conspire, on the one hand, and how to be caught defenseless against a conspiracy and be its victim, on the other. So that we can see what power and conviction look like in real terms, as well as the costs of hubris, and recklessness.
And because winning is typically preferable to losing, this book is about how one man came to experience what Genghis Khan supposedly called the greatest of life’s pleasures: to overcome your enemies, to drive them before you, to see their friends and allies bathed in tears, to take their possessions as your own. The question of justice is beside the point; every conqueror believes their cause just and righteous—a thought that makes the fruits taste sweeter.
“We live in a world where people don’t think conspiracies are possible,” Thiel would tell me. “We tend to denounce ‘conspiracy theories’ because we are skeptical of privileged claims to knowledge and of strong claims of human agency. Many people think they are not possible, that they can’t be pulled off.”
In these pages, I seek to show you, step by step, not a conspiracy theory but an actual conspiracy as explained by the people who did pull one off. I also seek to show you the consequences and the causes. 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.
PART I
The Planning
CHAPTER 1
The Inciting Incident
“The beginnings of all things are small,” Cicero reminds us. What becomes powerful or significant often begins inauspiciously, and so, too, do the causes that eventually pit powerful forces against one another.
The conflict at the heart of this story is no different. Its genesis is a largely obvious, mostly unremarkable blog post—not even four hundred words long—that outed a little-known technology investor as homosexual. Written by a gossip blogger named Owen Thomas, for a now-defunct tech news website owned by Gawker called Valleywag, the piece was published at 7:05 p.m. on December 19, 2007, under a headline that would sear itself into the mind of its subject:
