WEB OF LIES

AN UNDERGROUND, ANONYMOUS INTERNET— THE DEEP WEB—IS A HAVEN FDR LAWLESSNESS. BUT NOTHING COULD SAVE ITS KINGPINS FROM THE PAINFUL CONSEQUENCES OF HUMAN ERROR _ 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 circula­tion 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 fcith people. Ulbricht, with his easy smile and thick mop of brown hair, was dressed in blue jeans and a T-shirt. The handful 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 well educated, with a master's degree in materials science and engi­neering from Penn State. He was a good son from a good Texas family, an un­likely addition to the list of men who had changed the shape and scale of drug dis­tribution in America. But like Pablo Escobar, who used small planes to flood the U.S. with Colombian cocaine in the 1970s and 1980s, and Joaquin Guzman Loera, who led Mexico's Sinaloa cartel to deploy sub­marines, freight trains and a Boeing 747 to move billions of dollars in narcotics over the past decade, Ulbricht did more than just move drugs: He revolutionized the drug-trafficking indus­try altogether, bringing it into the digital age. Authorities charged that Ulbricht, under the handle Dread Pirate Roberts, op­erated Silk Road, an online marketplace where mari­juana, heroin, cocaine, LSD and other drugs were freely traded, along with passports, feke IDs, software for hackers and identity thieves, and all manner of contraband. Illicit goods were delivered to buyers by neighborhood mail carriers in packag­ing as inconspicuous as any book or DVD from Amazon. By the time agents arrested Ulbricht, he had made a small fortune in commissions on roughly $200 million in drug sales alone. Authorities called it the world's largest and most sophisticated online marketplace for illegal goods. It had gotten there in under three years. On February 4, after a highly publicized trial, Ulbricht was found guilty on all seven counts of money laundering, narcotics trafficking and computer hack­ing that had been brought against him. Trade on Silk Road flourished in part because of the security and anonymity it provided its customers, who could make purchases from sellers rated and reviewed much as they are on other online marketplaces. Just as Amazon changed what it means to be a bookseller, Silk Road changed what it means to be a drug dealer, small-arms vendor or identity thief by mak­ing it possible for users to order illicit (continued an page 116) WEB OF LIES Continued from page 56 goods without the inconvenience and dan­ger of face-to-face transactions. It was just one of countless sites on the "deep web," an anonymous version of the internet where pages are not indexed by Google and can be accessed only with special browsers such as Tor. By allowing users to visit hidden URLs anonymously, leaving no trace of their online activity, the deep web and Tor became popular with security-conscious dissidents, whistle-blowers, journalists— and criminals. Ulbricht and his successor, Blake Benthall, are two bright, privileged young men—men who went to college and became unlikely criminals for reasons difficult to fathom by family and friends, many of whom would comment only on the condition of anonymi­ty. Ultimately, theirs is a story about how the internet is changing crime and how crime is changing the internet. Silk Road first appeared in February 2011, but it was the rising popularity of Bitcoin, by then two years old, that made the site possible. A peer-to-peer digital currency both free from government over­sight and difficult to trace, Bitcoin's value is determined by supply and demand, mak­ing it popular among technologists and libertarians. For Ulbricht, who is both, it brought forth a world of possibilities. In January 2011 one Bitcoin was worth about 30 cents, up from less than a penny the year before. The relative anonymity pro­vided by the currency helped Silk Road users cover their tracks, and the site's rap­idly increasing business gave Bitcoin its first practical application. The site had re­ceived enough news coverage to gain the attention of Democratic senators Chuck Schumer and Joe Manchin, who called for its closure on June 6. Two days later, the value of a single Bitcoin topped $29. Silk Road enabled lawlessness, but Dread Pirate Roberts established laws of his own. Child pornography, prolific across the deep web, wasn't allowed on Silk Road. At first guns and other weapons were also banned, but in early 2012 dealers emerged selling everything from Glocks to Uzis, and Ulbricht allowed it. The evolution fit with Ulbricht's increas­ingly violent descent into the world of crime, which prosecutors said led him to spend several hundred thousand dollars in Bitcoins on contract killings to protect his criminal enterprise. (None of the hits appear to have been carried out.) Allowing gun sales on Silk Road also aligned with the libertarian beliefs prevalent on the site, values at the core of Ulbricht's mission to create a regulation-free marketplace that used anonymity and a decentralized cur­rency to drive transactions. It was, in other words, an experiment in economics and technology whose political underpinnings excited Ulbricht and other idealists as much as any criminal motive. In January 2012 a drug dealer known on Silk Road as "digitalink" was arrested: Jacob Theodore George IV, a 32-year-old Maryland man, had been selling heroin and methylone on the site for about three months. Prosecutors didn't waste the op­portunity to gain insight into the deep web's most popular drug marketplace. The arrest was kept quiet, and a plea agreement allowed authorities to obtain e-mails and financial re­cords to help them map Silk Road through its second year of business. Six months later, customs officers in Australia intercepted a package of cocaine and methylone ad­dressed to a Silk Road user named Paul Leslie Howard. Drugs, as well as scales, cash and 35 stun guns disguised to look like cell phones, were found during a subsequent raid of Howard's home. It became the first Silk Road-related arrest to make interna­tional headlines. In America, more arrests gave the government a network of infor­mants to help navigate Ulbricht's world, spawning a cross-agency law-enforcement effort dubbed Operation Marco Polo, after the explorer who first wrote about the site's namesake trading route. In the end, it was no high-tech game of cat and mouse that landed Ulbricht in handcuffs. It was a man named Curtis Clark Green, one of a handful of employ­ees Ulbricht paid thousands of dollars each month to help run his site. In January 2013 Green was arrested after taking delivery of a kilogram of cocaine in a deal personally brokered by Ulbricht. Green quickly be­trayed his employer by agreeing to cooper­ate with authorities, but it would prove to be less of a turn than the one Ulbricht had in mind for Green, who Ulbricht thought had been skimming Bitcoins from the site's coffers. Chat logs show that, after learning of Green's arrest, Dread Pirate Roberts of­fered a Silk Road user $80,000 to kill his former employee. What he didn't know was that the contract killer he'd chosen— user name "nob"—was a federal agent. In cooperation with authorities, Green played the part of murder victim in staged photos sent to Ulbricht as evidence that the deed had been done; "nob" messaged Ulbricht that Green had "died of asphyxiation/heart rupture" during torture. Later "hits" would turn out to be apparent scams perpetrated against an unwitting Ulbricht, who had no idea how to actually commission a murder. The day after his arrest, users visiting Silk Road were greeted with a message from the Department of Justice and the FBI: "This hidden site has been seized." II On a quiet Sunday morning last March, Blake Benthall woke before sunrise at his home in San Francisco's Mission district. It had been more than a year since the 26-year-old had moved to the two-story house, which, despite its odd green and yellow color scheme, didn't warrant a second look in the eccentric city. Even Benthall realized its charms were hidden; he'd nicknamed it the Ship House, after an old model ship that hung in a bay window facing the street. "An hour away from boarding Startup Bus," he wrote on Facebook that morning. "Three days in a bus with strangers, building a com­pany to pitch to investors waiting in Austin. Second year doing this, crazy excited!" Those strangers would soon become friends, teammates and competitors. Some were software engineers like Benthall, while others were designers, businessmen and marketers. Once aboard, each would take a microphone at the front of the bus and pitch an idea, the strongest of which would be developed in groups over a three-day hackathon—a frenzied but not unheard-of pace. Some participants had start-ups of their own, funded by such noted investors as Mark Cuban; others worked for companies like Google and were accustomed to deal­ing with high-pressure deadlines. When the bus arrived, their reward would be harsh critiques from celebrity judges and investors who would then select a winner and possibly offer funding to the most promising groups. Benthall had taken his first Startup Bus trip in 2013 with his friend Falon Fatemi, chief executive of a secretive tech start-up named Close. Fatemi had been the "conduc­tor," rallying friends and associates to come along. Benthall performed impressively that year, reaching the competition's finals with a localized anonymous-messaging app called GhostPost, which allowed users to chat with one another at parties, sporting events and concerts." People loved the app, and we stole thunder from the group that presented be­fore us," one of Benthall's teammates tells me. "They used it to post funny messages on the screen, and it distracted the audience." Benthall's friends often describe him as a "typical software-engineer type." "He's a little stubborn, obviously sharp and kind of witty," the teammate says before explain­ing how Benthall hid his stronger person­ality traits and excesses. "He was definitely a libertarian, but he wasn't belligerent about it. And I never saw any signs that he was raking in a bunch of dough or that he was interested in drugs." But his passionate libertarianism and intense determination occasionally set him apart from his peers. As the Startup Bus arrived in San Antonio for the semifinals, many groups had a prototype to present to the judges, but Benthall's had two: one ver­sion from his team and one he'd developed himself. "He decided his way of building a prototype was better, so he separated him­self from the team," says the teammate. Later that year, on November 6, 2013, someone the FBI refers to as DPR2, or Dread Pirate Roberts 2, launched Silk Road 2.0. It had been less than a month since Ulbricht's arrest. When the site went live, it displayed a message boldly mocking the one authorities had left after seizing the original Silk Road: "This hidden site has risen again." A week later, Benthall joined Silk Road 2.0 as an administrator under the user name Defcon. Over the next month he would be given two opportunities to step off the path he had chosen: First, he landed a soft­ware engineer's dream job at Elon Musk's SpaceX, where he would jokingly tell friends he was a rocket scientist. Then, on Decem­ber 20, three former Silk Road administra­tors were arrested. Defcon posted an urgent message to users on the site's forums later that day. "Three of our dear friends were arrested in connection to their Silk Road 1.0 activities," he wrote. "They did not have ac­cess to anything which would compromise the marketplace. We are watching every­thing very closely regardless." DPR2 saw the writing on the wall and abandoned the site he had created. Benthall stayed, and on December 28 he announced he would be taking over with a stump speech to assure users they were in good hands. "I intend to prove to you that lead­ing this movement forward is my top prior­ity in life." he wrote, "and that I will pour any time and energy necessary into ensur­ing its success. I'm ready to fight right here alongside you." He soon quit his dream job at SpaceX. In the dark comers of the deep web, he had found a new frontier to explore. The marketplace quickly picked up where the original Silk Road had left off. On Janu­ary 14, 2014, just a few weeks after assum­ing control of the site, Defcon announced he would personally decide how much com­mission to charge on each sale. He justified the commission scale, which ranged from four to eight percent, by talking about the risks he and his staff were taking on. "I have no doubt that we have the highest traf­fic," he wrote, referencing the site's grow­ing popularity. "Purchases are going up, vendors are going up—and alongside this, the amount of personal risk staff is taking is exponentially going up. The bigger we become, the more resources agencies are willing to spend on hunting us." But at that point the hunt had been go­ing on far longer than Benthall could have imagined. Even before he joined the site, an undercover federal agent had been hired to moderate its discussion forums. With almost total access to its inner work­ings, the insider helped the FBI locate one of the site's hidden servers abroad. In May 2014 foreign authorities made a copy of the server and delivered it to federal agents in the U.S. Benthall, like Ulbricht, grew up in Texas. He was raised in a Christian household in a large single-story home in Houston. In 2009 the promising young programmer dropped out of his sophomore year of college in Flori­da and took a computer-programming posi­tion at RPX Corporation in San Francisco's financial district. The Texas boy did not stand out in the city, where a generation of precocious programmers had flocked to find work that matched their ambitions. Although Benthall kept his religious be­liefs quiet around friends in the tech com­munity, he clung to his Christian values. He volunteered at San Francisco City Impact, a ministry dedicated to helping the poor and homeless in the Tenderloin district, the city's skid row. The ministry's human resources director, Hayley Duerstock, says Benthall was well liked around their offices, situated just oflfTurk Street in one of the Tenderloin's most crime-plagued areas, where drug deal­ers conduct business in plain sight. Benthall, however, living just a couple of miles south of the ministry, was by then surreptitiously fa­cilitating the sale of $8 million in illicit goods each month, generating at least $400,000 in monthly commissions. Drugs accounted for the majority of the sales, bought and sold among Silk Road 2.0's cloistered community of 150,000 active users, who, by the grace of Benthall, lived above the fray, a long way from Turk Street. At City Impact Benthall met his girl­friend, Stephie, who worked there as an in­tern. In spring 2014, the couple announced their relationship on Facebook by sharing a photo of a romantic walk on the beach. Some of Benthall's friends were surprised: "A girl!!!! OMG Blake Benthall," one wrote; "Get a room," wrote another. The couple had been close well before Benthall took on his Defcon alter ego, but as he expanded the site's reach, the two only grew closer. In just a handful of years, the young software engineer had conquered a town known to run through ambitious techies like Hollywood runs through aspiring young stars. And though he told a neigh­bor he often missed his mother, he was able to maintain his Christian faith and find someone to share it with. Last August, Blake hiked in Oregon and Washington with Stephie and his parents, Larry and Sharon Benthall. Together they posed for photos among evergreens lining steep cliffs overlooking the Pacific. Benthall appears serene and unworried alongside his girl­friend as they pose in front of Mount Rain­ier; a few days earlier, on July 30, he had transferred Silk Road 2.0 onto a new hid­den server, according to court documents. But federal agents had been watching Benthall for months. The FBI's under­cover operative had the kind of access nec­essary to explore the site's architecture and interacted with Benthall regularly. While a case was built from the inside, other agents tracked his day-to-day movements. They watched as he placed a $70,000 down payment on a Tesla Model S using Bitcoins—a rare indulgence for Benthall. Like the rest of Benthall's secret life, the Tesla went basically unnoticed. "It's not an unusual car to see in San Francisco," one of Benthall's friends tells me. Another says he heard Benthall paid for it with money he'd earned doing consulting work. On November 5 of last year, as Benthall pulled the car into the street, he was swarmed by 20 FBI agents who approached the vehicle with guns drawn. They took him into custody without incident. According to prosecutors, he quickly admitted to every­thing he'd been accused of in the federal in­dictment outlining Defcon's crimes, which included charges of computer hacking, money laundering and narcotics trafficking. In the months after Benthall's arrest, his girlfriend's Facebook cover photo changed to display an image of the couple embrac­ing, with a heart covering their faces and the word faith typed over it. Above the image was a reference to Hebrews 4:16. "Let us there­fore come boldly unto the throne of grace," the passage reads, "that we may obtain mercy, and find grace to help in time of need." Ill Two days later, it became clear that Silk Road 2.0 wasn't the only corner of the deep web authorities had been monitor­ing. On November 7, while Benthall ate his second breakfast in federal custody, law-enforcement agencies in the U.S. and abroad executed coordinated raids in 16 countries as part of Operation Onymous, an effort to seize a number of hidden sites operating on Tor. It was an unprecedented move to curb crime on the deep web, as well as a statement about the kinds of sites au­thorities planned to target. The sweep re­sulted in 17 arrests and the seizure of drugs, cash and about a million dollars in Bitcoins. Authorities announced the confiscation of 27 hidden sites—most of them illicit mar­kets similar to Silk Road 2.0—as well as a number of servers that hosted them. Tremors immediately shot through on­line communities that had a stake in keeping the deep web anonymous. Privacy and free speech advocates, journalists, Bitcoin en­thusiasts, political dissidents and criminals all struggled to make sense of how sites de­signed to be anonymous and servers meant to be hidden had been found. Some were hopeful that law enforcement had relied on informants, insiders and holes in site admin­istration to carry out their raids, while others worried that fissures had been discovered in Tor's code and that encryption once thought unbreakable had been cracked. Speculation abounded that police were able to follow a trail of Bitcoins from illegal deep-web trans- actions to real-world payments, such as the one Benthall had made for his Tesla. The scope of Operation Onymous, how­ever, was broader than the illicit sites it confis­cated, and its implications extend beyond cy­bercrime into the realms of free speech and government surveillance (even if it requires a dictionary to realize—onymous is an antonym of anonymous). Peter Carr, a spokesperson for the Department of Justice, says the full roster of seized websites reaches "well beyond the 27 identified," but it would take time for the various law-enforcement agencies involved to assess the extent of Operation Onymous. Until the government shows its hand, it's hard to say definitively whether Tor has been cracked or not. What is known, however, is that Operation Onymous relied heavily on informants, undercover agents and detective legwork to bring down its targets. At Tor Project's modest Cambridge, Mas­sachusetts headquarters, the November 7 raids came as a most unwelcome surprise. Tor's 30 employees have nothing to do with illegal sites such as Silk Road, but they de­cided to scrap their weekend plans for an all-hands-on-deck effort to uncover how their network may have been compromised. For days they attacked their own code to expose vulnerabilities law enforcement may have exploited to crack Tor. They found nothing. Leading the effort was Tor's executive director, Andrew Lewman, who knows pre­cisely how vulnerable citizens can be online. Once the vice president of engineering at a major online marketing company, he helped design the systems that originally eroded privacy on the internet. "It doesn't seem to be bugs in our code," he told me in the immediate aftermath of Operation Onymous, "but we're working at it, trying sophisticated attacks and very stupid ones. You never know where you might have a weakness. Sometimes, people get lucky." Months later, Lewman remains convinced that Operation Onymous was a product of luck. "Tor is still safe," he tells me in January, a reassurance no one would have thought to ask for prior to Onymous, when Tor was still considered unbreakable—even by the National Security Agency, according to documents leaked by Edward Snowden. Ironically, the U.S. government under­stands exactly how effective Tor is as a tool for secure browsing and communication, because the government created it. In the mid-1990s, "the onion router" method of online anonymity was developed at the U.S. Naval Research Laboratory. Its name follows from the logic behind its core functionality, which places multiple layers of connection between users and the sites they access. The Tor browser thwarts electronic surveillance and tracking by sending user page requests through three randomly selected relays in its network of 6,000 volunteer-run servers. These relays act as layers—hence the onion—that protect users from direct con­nections with hidden sites. When someone in Nebraska visits a hidden site, his page re­quest might first be routed through a server in Vermont, where his IP address could the­oretically be identified; then it would filter through a second relay, where neither pre­vious IP address could be identified; finally, it would reach a third server, which sends it on to its destination—the only part of the puzzle the final relay can see. The whole process is wrapped in encryption, making it extremely difficult, though not impossible, for law enforcement to infiltrate hidden sites accessible on the Tor network. Tor was designed to keep U.S. intelligence secrets secure, and it worked well enough that the Department of Defense developed the project further at the Defense Advanced Research Projects Agency, or DARPA, the federal agency responsible for producing a precursor to GPS technology and for creat­ing the competition that birthed the self-driving car. The Tor Project, a nonprofit group, took up the cause on behalf of civil­ians a few years later, releasing the first ver­sion of the browser publicly in 2002. For nearly a decade after its public launch, not a bad word was said about Tor. As it grew, the anonymous network became unambiguously known as a tool of free speech and a facilitator of peaceful demo­cratic resistance in repressive societies. But just as crime flourished at the frontier of the early commercial internet in the 1990s, so too have criminals taken to the deep web at an alarming rate since the arrival of Bit-coin, which gave Silk Road and similar sites the means to anonymously monetize their operations. Today, Tor's public image is decidedly more complicated, and not just because of Silk Road. Operation Onymous's big trophies in­cluded Silk Road 2.0 and other illicit mar­kets. But the raid also saw noncommercial sites built for the Tor network targeted by law enforcement for the first time. Doxbin, a repository for posting names, addresses and Social Security numbers for the benefit of identity thieves and fraudsters, was one of several sites closed without a clear legal basis. Pink Meth, an extreme example of a website genre called revenge porn, was also shut down. At Pink Meth, stolen nude photographs of women from around the world were posted alongside their per­sonal information, often including links to Facebook, Twitter and Linkedln profiles. In some cases, e-mail addresses and other contact information were included as well. Shelby Conklin, a 22-year-old recent col­lege graduate from northern Texas, was one of the site's victims. Conklin's photos were sto­len from a hacked Photobucket account, ac­cording to her attorney, Jason Van Dyke, who says she had to delay pursuing a career until she could be sure the images wouldn't turn up in a background check. Most photos that end up as re­venge porn are made in the context of a relationship and then leaked by the man af­ter it sours—"and it's always the man," Van Dyke says—but Conk-lin's case was unique in that her photos were stolen by strang­ers from a private on­line storage account. Just days after Operation Onymous took down the site, Conklin walked into a Texas courtroom and won a default judg­ment against Pink Meth in a civil case that began early last summer. She doesn't expect to see any of the million-dollar judgment. "To this day we don't know the identity of a single person associated with Pink Meth," Van Dyke tells me, a sign that, without infor­mants, the govern­ment's ability to po­lice the deep web may still be limited. For some activists, there are concerns that the challenges of policing a digital realm like the deep web, where users are anonymous and sites are often legally ambiguous, could push police to bend legal frameworks in the name of justice. Those concerns have been exacer­bated by the fact that police agencies have yet to publicly acknowledge their seizure of noncommercial Tor sites such as Pink Meth and Doxbin or to explain which laws the sites violated. Conklin's lawsuit also underscores just how much public confusion remains about the deep web. When Van Dyke initially brought suit against Pink Meth, he listed Tor as a defendant, believing the organiza­tion existed solely to facilitate online crime. It was akin to filing suit against Google over an illegal image in your search results. Lew-man emphasizes that the sole purpose of the Tor Project is to facilitate free speech; Van Dyke, widely ridiculed online for mis­understanding Tor and its potential liabil­ity, soon dropped the organization from his suit. "I would compare Tor to a handgun," the conservative Texan says. "It can be used by good people to do good things, but in the wrong hands it can cause terrible harm." On the morning of the Onymous raids, police in the Netherlands seized three volunteer-run Tor servers. How police un­covered the relays—and the legal basis on which they were seized—remains a mystery. Lewman says the Tor Project collaborates with law-enforcement authorities to help them understand the deep web so they can enforce existing laws. Lewman also works with women who have been victimized by sites like Pink Meth, and while he is happy to see these sites leave the deep web, watch­ing them be seized quietly and with no le­gal basis raises fears about what might come next. Lewman worries that more lines will be crossed as police adapt to technologies that strain already overburdened depart­ments and agencies, and that precedents will be set that can't be recalled. "I worry about legislating technology," he says. "If you leg­islate Tor, that can create real problems, be­cause once the technology moves on, you're left with laws that no longer fit the world you live in. We have to be able to adapt." Around the world, governments are draw­ing their own lines when it comes to dealing with the deep web. In 2009 several thousand users were logging on with the Tor browser each day in mainland China. Then, in early 2010, the traffic suddenly dropped to almost nothing and has remained that way since. IV FBI special agent Vincent D'Agostino spent the summer of 2010 working to put away a prominent underboss from New York's Colombo crime family. John "Sonny" Fran-zese Sr. was 93 years old when his racketeer­ing trial began that June, but old age hadn't made him sentimental: As Franzese looked on from his wheelchair, D'Agostino told the court that the Mob boss had ordered a hit on his own son after learning he'd worn a wire for the FBI. What Franzese hadn't known was that D'Agostino had more than one well-placed infor­mant in the Colombo syndicate. When Son­ny had asked Gaetano "Guy" Fatato to kill John Franzese Jr., the would-be hit man had been work­ing with the FBI for 15 months. Even­tually Fatato would spend two full years helping D'Agostino collect more than 1,000 hours of tape-recorded con­versations between Sonny and his co-conspirators. As part of a spe­cial FBI team called C-38, D'Agostino worked cases that, according to The Washington Post, "dec­imated" the Colom­bo crime family and "severely disrupted" the Bonanno fam­ily, one of four other syndicates that once waged war on the streets of New York City. With the Mob all but destroyed, D'Agostino took on a new challenge as his career entered its second decade: He joined the FBI's cybercrimes unit, where he would hunt hackers, online fraudsters and, eventually, Blake Benthall. Benthall's comments in the Silk Road 2.0 forums, posted under the Defcon moniker, reveal his idealism. He spoke of the site as an experiment in freedom, a place of ref­uge against unnamed "oppressors." But behind his rhetoric was a business that had more in common with the Mob than with a tech start-up. He didn't solicit murder as Ulbricht had, but Benthall made millions offering protection to the vast network of criminal enterprises that thrived in his mar­ketplace. And despite the technology in­volved, Benthall's was a business of relation­ships, one of which would be his undoing. It was misplaced trust in an undercover agent—a human failure, one no firewall or encryption software can protect against— that gave the FBI everything it needed to tie Benthall to Defcon and land him in federal custody. Benthall failed techno­logically as well. On January 5, 2014, in a forum post, he urged Silk Road 2.0 users to take all necessary precautions when it came to security and anonymity. "We are the biggest market on the darknet at this point," he wrote. "We are in a position to teach an incredibly valuable life skill to this buyer community: always encrypt." It was sound advice, but as any good hacker will tell you, digital security tools can't protect users from their own bad habits. Benthall's included inconsistent use of the very encryption methods that kept deep-web sites hidden from authorities in the first place. While administering Silk Road 2.0, Benthall used Tor and took appropriate anonymity measures, but he was lazy about security when it counted. When authorities took Silk Road 2.0's servers off-line to copy them, it caused an outage, which Benthall handled the way one might deal with an un­known phone-bill charge: He complained, using support tickets sent from ordinary web browsers easily matched to his laptop. He also accessed customer-support portals for Silk Road 2.0's server over the internet, using wi-fi in a hotel room he'd booked un­der his own name. There are a number of less obvious ways people hosting hidden sites can leave themselves vulnerable to de­tection, but few suspected Silk Road 2.0's operator would be caught playing so fast and loose with his own digital security. For Benthall's friends in the tech com­munity, the only thing more shocking than his second life as Defcon was how many commonsense deep-web rules he broke. "I'm no criminal mastermind," one tells me, "but even I know to cover my tracks better than he did." As quickly as Silk Road 2.0 emerged to replace Ulbricht's original drug bazaar, some sites that had been seized in Opera­tion Onymous returned to the deep web. Doxbin was restored to full operation just one week after the Onymous raids con­cluded, and on January lla new hidden site called Silk Road Reloaded launched, bringing with it a renewed set of security challenges for law enforcement. Accessible only with a new deep-web browser called IP2, Silk Road's latest iteration requires the reconfiguration of one's computer to work. Speculation abounds that it is even more secure than Tor. As an added layer of secu­rity, Silk Road Reloaded accepts an alterna­tive cryptocurrency, which it then converts into Bitcoins on its own, making transac­tions even more difficult to trace. Lewman, for his part, is leading his organization in the ongoing testing and strengthening of Tor's code. "The compa­nies that made armored vehicles used in Iraq built them to withstand bullets," he says by way of comparison. "But then they had to outfit them to resist improvised ex­plosive devices as well." On January 13 a dozen protesters gath­ered outside downtown Manhattan's fed- eral courthouse. Some held signs that read web hosting is not a crime! Another obscured his face with a black T-shirt worn as a makeshift balaclava and held a small placard emblazoned with the chosen one and a Bitcoin logo. Inside the stately courthouse, the chosen one himself, Ross Ulbricht, stood trial. His attorney claimed that Ulbricht created Silk Road as a radical economic experiment that he quickly aban­doned, only to be reeled into a life of crime by tech-savvy drug dealers. The following week, testimony from Special Agent Tom Kiernan cast serious doubt on those claims. After Ulbricht was arrested, Kiernan went to work on Ulbricht's Samsung 700z laptop. For three hours he took photo­graphs of Ulbricht's browser history and explored the hard drive; afterward, anoth­er agent copied its contents. It would prove to be better than a smoking gun. Spread­sheets of Silk Road finances and years' worth of Tor chat logs gave the jury a small taste of what Kiernan had gleaned. Docu­ments outlined the banal minutiae of a drug empire, including payroll sheets and notes on staff promotions. Like any busi- ness owner, Ulbricht kept scanned copies of his employees' ID cards on file. During the trial, Assistant U.S. Attorney Timothy Howard read chat logs from a 2013 conversation in which Ulbricht assured a Silk Road seller that authorities didn't have the technological facility to get their hands on the kind of unencrypted information they would need to build a case against the site. "Put yourself in the shoes of a prosecutor trying to build a case against you," he wrote. "When you look at the chance of us getting caught, it's incredibly small." But Ulbricht failed to put himself in the shoes of Vin­cent D'Agostino and other agents like him, agents who don't need to rely on technology to build their cases. Instead, Ulbricht built a case against himself on his laptop in the form of meticulous records of every crime he'd committed. All the agents at Glen Park Li­brary needed to do was reach out and grab it. In other cases, detective work as unsophis­ticated as a Google search led investigators to their suspects. In court, IRS Special Agent Gary Alford testified that he originally tied Ulbricht to his drug empire by searching the web for its Tor address, which led to an ac­count on BitcoinTalk.org that advertised Silk Road's earliest iteration. Later, a job posting for a web developer asked interested can­didates to e-mail [email protected]. In court, prosecutors used selfies Ulbricht had sent from the account to prove it was his. Ulbricht's defense relied on the idea that he had indeed run the site at one point, but soon a different Dread Pirate Roberts took over, who truly ran Silk Road. But with hun­dreds of pages of evidence directly tying Ul­bricht to Silk Road and his DPR handle, and a weak defensive strategy in court, Ulbricht was found guilty of all charges. Blake Benthall seems to have chosen a different path. On November 21—less than three weeks following his arrest in San Francisco, after which prosecutors had la­beled him an extreme flight risk—Benthall was released from the custody of the Fed­eral Bureau of Prisons. Court filings from December suggest a reason behind the change of heart, with references to discus­sions between prosecution and defense at­torneys about "a possible disposition of this case." In other words, the two sides are ne­gotiating. Benthall's current whereabouts are unknown, and his lawyers and family have not returned calls for comment. If he decides to cooperate with authorities and help lead them to other arrests, he may find some measure of the mercy mentioned in Hebrews 4:16. In the eyes of Silk Road's true believers, however, it is Ulbricht who went boldly unto the throne of grace. Perhaps the most damning evidence intro­duced in Ulbricht's trial was a personal diary he kept on his laptop, dating back to 2010. He detailed his struggle to hold a job, his failed efforts at an early start-up, his rocky re­lationship with his girlfriend. In an attempt to create interest in the site, he wrote about growing several kilograms of psychedelic mushrooms to sell on it before he'd even set up a server. "In 2011, I am creating a year of prosperity and power beyond what I have ever experienced before," he wrote. "Silk Road is going to become a phenomenon." The journal chronicled his thoughts dur­ing the site's growth—its first mainstream press coverage, mistakes made and lessons learned, and growing paranoia amid back-breaking work to administer his empire. He wrote about feeling guilty for the half-truths he perpetuated to hide Silk Road from his closest friends. In his last entry, from New Year's Day 2012, he described a day at the beach: "I imagine that some day I may have a story written about my life, and it would be good to have a detailed account of it." He played paddleball, sun­bathed with his friends and turned down invitations to warehouse parties and camp­ing trips for fear of spending too much time away from the site. If he weren't at the helm of one of the internet's largest criminal en­terprises, he'd be any other 20-something in San Francisco. "I've been thinking a bunch about what is next for me," he con­cluded, contemplating moving to Thailand or Australia. "I need to find a place I can work from. Cheap and off the beaten path."