54 I At 3:15 P.M. on October 1, 2013, Ross Ulbricht’s career as a drug kingpin came to an end in the science- fiction section of San Francisco’s Glen Park Library. The 29-year- old had walked up the steps just inside the modern stone building, passed the librarian working at the circula- tion desk and taken a seat at a far corner table near a window. It was a sunny day, but the small community library was filled with people. Ulbricht, with his easy smile and thick mop of brown hair, was dressed in blue jeans web of lies_ AN UNDERGROUND, ANONYMOUS INTERNET— THE DEEP WEB—IS THE LAST LAWLESS FRONTIER ON EARTH. BUT NOTHING COULD SAVE ITS KINGPINS FROM THE PAINFUL CONSEQUENCES OF HUMAN ERROR BY JOSHUA HUNT and a T-shirt. The hand- ful of people reading and wandering among rows of novels nearby weren’t dressed much differently, but beneath their shirts and jackets they wore vests that identified them as FBI agents. Until the moment they rushed Ulbricht, pushing him up against a window to handcuff him as other agents seized his laptop before he could lock it down, nobody suspected anything out of place. The cuffs went on and a small crowd gathered, but Ulbricht just looked out at the afternoon sun. Ulbricht was an educated person, with a master’s degree in 55 materials science and engi- neering from Penn State. He was a good son from a good Texas family, an un- likely addition to the list of men who had changed the shape and scale of drug distribution in Amer- ica. But like Pablo Escobar, who used small planes to 2_ flood the U.S. with Colom- bian cocaine in the 1970s and 1980s, and Joaquín Guzmán Loera, who led Mexico’s Sinaloa cartel to deploy submarines, freight trains and a Boeing 747 to move billions of dollars in 1_ narcotics into major U.S. cities over the past decade, Ulbricht did more than just move drugs: He revolution- ized the drug- trafficking in- dustry altogether, bringing it into the digital age. Authorities allege that Ulbricht, under the handle Dread Pirate Roberts, oper- ated Silk Road, an online 3_ marketplace where mari- juana, heroin, cocaine, LSD and other drugs were freely traded, along with passports, fake IDs, software for hackers and identity thieves, and all man- ner of contraband. Illicit goods were delivered to buyers by neighborhood mail carriers in packaging as inconspicuous as 4_ any book or DVD from Amazon. By the 1_ Portrait of a time agents arrested Ulbricht, authorities modern drug lord: say, he had made a small fortune in com- what it means to be a book seller, Silk Road changed what it Ross Ulbricht takes a selfie.2_ Silk missions on roughly $200 million in drug means to be a drug dealer, small-arms vendor or identity thief Road 2.0 leader sales alone. They called it the world’s by making it possible for users to order illicit goods without Blake Benthall largest and most sophisticated online the inconvenience and danger of face-to-face transactions. It with his girlfriend. marketplace for illegal goods. It had got- was just one of thousands of sites on (continued on page 116) 3_ Ulbricht’s fake IDs, never used. ten there in under three years. 4_ An eBay for Trade on Silk Road flourished in part many illegal items: because of the security and anonymity it “I’D COMPARE TOR TO A HANDGUN,” SAYS A screen shots of Silk provided its customers, who could make Road and its FBI- TExAS ­lawyer. “IT CAN BE USED BY GOOD mocking successor, purchases from sellers rated and re - Silk Road 2.0. viewed much as they are on other online PEOPLE TO DO GOOD, BUT IN THE WRONG marketplaces. Just as Amazon changed HANDS, IT CAN CAUSE TERRIBLE HARM.” PEELING THE ONION_ THE DEEP WEB RELIES ON A network CALLED TOR—THE SELLER_ ONION ROUTER—TO PROvIDE The process ANONYMITY. HERE’S HOW repeats for users on the server’s encrypted server_ supply side. In an instant, one If Tor is set of 6,000 volunteer- up correctly run Tor relays fields and no foolish the page request, mistakes are then encrypts its made, the origins and sends site_ seller’s biggest it to another. Wash, Users range risk lies in rinse and repeat from activists in finally mailing BUYER_ twice more. censor-happy that kilo. The chain begins with nations to those anyone savvy enough looking for a fix. to run the Tor browser By the time a Tor (it doesn’t take much). server is reached, Enter a .onion URL, and tracing its source Tor seeks out a relay to is impossible. 56 conceal your identity. marketplace that utilized anonymity and a had been more than a year since the 26-year- decentralized currency to drive transactions. old had moved to the two-story house, It was, in other words, an experiment in which, despite its odd green and yellow economics and technology whose political color scheme, didn’t warrant a second look underpinnings excited Ulbricht and other in the eccentric city. Even Benthall realized idealists as much as any criminal motive. its charms were hidden; he’d nicknamed it In January 2012 a drug dealer known the Ship House, after an old model ship that on Silk Road as “digitalink” was arrested: hung in a bay window facing the street. “An Jacob Theodore George IV, a 32-year-old hour away from boarding StartUp Bus,” he Maryland man, had been selling heroin wrote on Facebook that morning. “Three and methylone on the site for about three days in a bus with strangers, building a com- m months. Prosecutors didn’t waste the op- pany to pitch to investors waiting in Austin. portunity to gain insight into the deep web’s Second year doing this, crazy excited!” the clandestine constellation most popular drug marketplace. The arrest Those strangers would soon become was kept quiet, and a plea agreement al- friends, teammates and competitors. Some Continued from page 56 lowed authorities to obtain e-mails and fi- were software engineers like Benthall, while nancial records to help them map Silk Road others were designers, businessmen and the “deep web,” an anonymous version of through its second year of business. Six marketers. Once aboard, each would take the internet where pages are not indexed months later, customs officers in Australia in- a microphone at the front of the bus and by Google and can be accessed only with tercepted a package of cocaine and MDMA pitch an idea, the strongest of which would special browsers such as Tor. By allowing addressed to a Silk Road user named Paul be developed in groups over a three-day users to visit hidden URLs anonymously, Leslie Howard. Drugs, as well as scales, cash ­­hackathon—a frenzied but not unheard- leaving no trace of their online activity, and 35 stun guns disguised to look like cell of pace. Some participants had start-ups of the deep web and Tor became popular phones, were found during a subsequent their own, funded by such noted investors as with security- conscious dissidents, whistle- raid of Howard’s home. It became the first Mark Cuban; others worked for companies blowers, journalists—and criminals. Silk Road–related arrest to make interna- like Google and were accustomed to deal- This is a story about two bright, privi- tional headlines. In America, more arrests ing with high-pressure deadlines. When the leged young men—men who went to col- gave the government a network of infor- bus arrived, their reward would be harsh lege, held good jobs and became unlikely mants to help navigate Ulbricht’s world, critiques from celebrity judges and investors criminals for reasons difficult to fathom by spawning a cross-agency law-­­enforcement who would then select a winner and possibly family and friends, many of whom would effort dubbed Operation Marco Polo, after offer funding to the most promising groups. comment only on the condition of ano- the explorer who first wrote about the site’s Benthall had taken his first StartUp Bus nymity. It is a story about how the internet namesake trading route. trip in 2013 with his friend Falon Fatemi, is changing crime and how crime is chang- In the end, it was no high-tech game chief executive of a secretive tech start-up ing the internet. of cat and mouse that landed Ulbricht named Close. Fatemi had been the “conduc- Silk Road first appeared in February in handcuffs. It was a man named Curtis tor,” rallying friends and associates to come 2011, but it was the rising popularity of Clark Green, one of a handful of employ- along. ­­Benthall performed impressively that Bitcoin, by then two years old, that made ees Ulbricht paid thousands of dollars each year, reaching the competition’s finals with a the site possible. A peer-to-peer digital cur- month to help run his site. In January 2013 localized anonymous-messaging app called rency both free from government oversight Green was arrested after taking delivery of GhostPost, which allowed users to chat with and difficult to trace, Bitcoin’s value is de- a kilogram of cocaine in a deal personally one another at parties, sporting events and termined by supply and demand, making it brokered by Ulbricht. Green quickly be- concerts. “People loved the app, and we stole popular among technologists and libertar- trayed his employer by agreeing to cooper- thunder from the group that presented be- ians.