How the Dark Web’s Dread Pirate Roberts Went Down

CreditCreditErik Carter


The Epic Hunt for the Criminal Mastermind Behind the Silk Road
By Nick Bilton
Illustrated. 329 pp. Portfolio/Penguin. $27.

When Ross Ulbricht created the Silk Road, a clandestine online drug bazaar hidden on the deep web, he was a 26-year-old libertarian idealist living in Austin, Tex., talking his girlfriend’s ear off about Austrian economics and seasteading experiments — the idea of creating communities in the middle of the sea, free from government regulations. For all his lofty ambitions, he felt like a failure. He had flunked his Ph.D. exam and was unable to find a buyer for his seasteading gaming simulation. But with the Silk Road he was able to marry his business ambitions and anti-authoritarian philosophy; he envisioned it as a powerful way to defy what he perceived to be the state’s irrational drug policies. Using an anonymizing browser like Tor and the cryptocurrency Bitcoin, people could discreetly buy and sell drugs. Ulbricht taught himself to code and he began by selling mushrooms that he grew himself.

By the time Ulbricht was arrested two years later, the Silk Road was an estimated $1.2 billion business that expanded into heroin, guns, hacking tools, counterfeit cash and cyanide. Ulbricht, a former Boy Scout, had tried to commission five murders as the Dread Pirate Roberts, the pseudonym under which he ruled the site. The obsessive, dizzying manhunt to apprehend him involved a slew of government agencies and ended with a neck-breaking plot twist: double agents and hundreds of thousands of dollars in missing Bitcoin.

Ulbricht is currently appealing a life sentence for seven convictions, including narcotics, money laundering and the kingpin statute, more typically applied to Mafia bosses or cartel leaders. Evidence unearthed by federal agents included his journal, along with nearly two million words of chat logs between Dread Pirate Roberts and his underlings detailing the operations of the site.

The weird details of the Silk Road bust and the contrast of the drugs and violence with Ulbricht’s wholesome past and G-rated vocabulary (his preferred expletives include “heck” and “fudge”) have proved irresistible to storytellers. The hit man for the first murder that Ulbricht allegedly commissioned was an undercover D.E.A. agent. Ulbricht’s target, a Mormon 47-year-old grandfather in Utah, had to fake his death by pouring a can of Campbell’s Tomato Soup on his face to look like blood. Is it any wonder that the Coen brothers are reportedly working on a screenplay?

There have already been two short documentaries about Silk Road, one by Vice and one by Alex Winters (Bill of “Bill & Ted’s Excellent Adventure”), as well as a series in Wired. Curtis Green, the Campbell’s Soup victim, is writing a memoir. The double agent has hinted at a movie deal as well. But “American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road,” the second book from the journalist Nick Bilton, a former technology columnist at The Times, is the most comprehensive narrative thus far.


The cast of characters has been established over the years since Ulbricht’s arrest, but Bilton’s impressive reporting gives more space to a story that could use some sprawl. For instance, close observers may remember Gary Alford, the criminal investigator with the I.R.S., who was the first agent to come across Ulbricht’s name in conjunction with the Silk Road. Previous accounts gave us the logistics, but Bilton’s book gives us psychological shading and insight into Alford’s method. Alford was born in Brooklyn in 1977, the summer the Son of Sam terrorized New York. It stuck with him that the N.Y.P.D. finally caught the serial killer by poring over parking tickets. He had a hunch he could ensnare Dread Pirate Roberts the same way, and began to look for a sloppy mistake. Sure enough, he discovered that Ulbricht left an anonymous comment on a forum called the Shroomery when he was trying to drum up attention for his new site. However, he had neglected to scrub his email address.

In Bilton’s account an unexpected symmetry emerges between the agents investigating Ulbricht and the kingpin himself. They’re all fighting feelings of inferiority and treating the Silk Road as a chance to prove themselves. Bilton’s focus is on the hunt, and the book seems determined to sustain the suspense, even when it’s baked into the plot. Many chapters end with a cliffhanger, which adds a cinematic quality but veers into pulpy true crime when it feels like there’s more pathos at stake. Sometimes the facts are more satisfying than the framing.

Bilton’s first book, “Hatching Twitter,” dug into the founding of the social media company. In “American Kingpin,” he ratchets up the tech industry parallels with good reason, but it can feel overdetermined. Ulbricht fits the archetype of the eccentric tech wizard, including pushing his body to extremes for intellectual purposes, like choosing to take cold showers for a month to test his resilience. But part of what makes this particular kingpin so fascinating is that Silk Road wasn’t incubated in Mountain View, Menlo Park or the antiseptic co-working spaces of San Francisco. Ulbricht accomplished “the equivalent of building eBay and Amazon on his own, without any help or any knowledge,” Bilton writes. Toiling away in a cramped bedroom in Austin, making millions without getting the cover of Forbes, he seemed driven by his outsider status.

Ulbricht’s rise and fall is like the start-up hero’s journey reflected in a black mirror. He was fond of the same Ayn Rand quotes as other founders: “The question isn’t who is going to let me; it’s who is going to stop me.” He had his own version of a consigliere, in the form of Variety Jones. (Ulbricht’s ex-girlfriend gets a lot of space, but the most tender and complex relationship of the book is between him and Variety Jones.)

Ulbricht also had the same blinkered view of the consequences of his actions. However, unlike the moral transgressions of the Uber C.E.O. Travis Kalanick or the Theranos C.E.O. Elizabeth Holmes, his came with chat logs. The documentation offers a small window into one of late capitalism’s best kept secrets: How these messianic entrepreneurs talk behind closed doors when they fall so far from their ideals. I wish there had been more focus on that rather than scenes inside a Samsung factory or yet another of Ulbricht’s beach vacations.

Since the arrest, Ulbricht’s situation seems decidedly less fringe. Libertarianism has rolled up into the Republican mainstream. The rhetoric that inspired him, from books by Murray Rothbard and Ludwig von Mises, has found its way into the Republican Party. Gawker, the site responsible for first reporting on Silk Road, is dead, bankrupted by Peter Thiel, the libertarian billionaire venture capitalist, Trump adviser and Facebook board member.

Like some other start-up founders, Ulbricht is undone by his naïveté and narcissism. “I remember clearly why I created the Silk Road,” he said at sentencing. “I wanted to empower people to be able to make choices in their lives, for themselves and to have privacy and anonymity.” The judge responded: “No drug dealer from the Bronx selling meth or heroin or crack has ever made these kinds of arguments to the court. It is a privileged argument. You are no better a person than any other drug dealer. ... You were captain of the ship, as the Dread Pirate Roberts, and you made your own laws and you enforced those laws in the manner that you saw fit.” As she handed down the sentence, she said: “It was, in fact, a carefully planned life’s work. It was your opus. You wanted it to be your legacy — and it is.”

Nitasha Tiku is a senior writer for Wired covering Silicon Valley.

A version of this article appears in print on , Page 13 of the Sunday Book Review with the headline: Tales From the Dark Web. Order Reprints | Today’s Paper | Subscribe