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 book­seller, 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. For ­Ulbricht, who is both, it brought ate with authorities, but it would prove to fore us,” one of ­Benthall’s teammates tells forth a world of possibilities. In January be less of a turn than the one Ulbricht had me. “They used it to post funny messages on 2011 one Bitcoin was worth about 30 cents, in mind for Green, who ­Ulbricht thought the screen, and it distracted the audience.” up from less than a penny the year prior. had been skimming Bitcoins from the site’s Benthall’s friends often describe him as The relative anonymity provided by the coffers. Chat logs show that, after learning a “typical ­software-­engineer type.” “He’s a currency helped Silk Road users cover their of Green’s arrest, Dread Pirate Roberts of- little stubborn, obviously sharp and kind of tracks, and the site’s rapidly increasing fered a Silk Road user $80,000 to kill his witty,” the teammate says before explain- business gave Bitcoin its first practical ap- former employee. What he didn’t know ing how ­Benthall hid his stronger person- plication. By the end of the summer, the site was that the contract killer he’d chosen, ality traits and excesses. “He was definitely had received enough news coverage to gain user name “nob,” was a federal agent. In a libertarian, but he wasn’t belligerent the attention of Democratic senators Chuck cooperation with authorities, Green played about it. And I never saw any signs that he Schumer and Joe Manchin, who called for the part of murder victim in staged pho- was raking in a bunch of dough or that he its closure. That same month, on June 8, tos sent to Ulbricht as evidence that the was interested in drugs.” the value of a single Bitcoin topped $29. deed was done; “nob” messaged Ulbricht But his passionate libertarianism and Silk Road enabled lawlessness, but that Green had “died of asphyxiation/ intense determination occasionally set him Dread Pirate Roberts established laws of heart rupture” during torture. Later “hits” apart from his peers. As the StartUp Bus his own. Child pornography, prolific across would turn out to be scams perpetrated arrived in San Antonio for the semifinals, the deep web, wasn’t allowed on Silk Road. against an unwitting ­Ulbricht, who had no many groups had a prototype to present to At first guns and other weapons were also idea how to actually commission a murder. the judges, but ­Benthall’s had two: one ver- banned, but in early 2012 dealers emerged This January Ulbricht went on trial, fac- sion from his team and one he’d developed selling everything from Glocks to Uzis, and ing charges of narcotics trafficking, money himself. “He decided his way of building a Ulbricht allowed it. laundering and computer hacking that prototype was better, so he separated him- The evolution fit with Ulbricht’s increas- could put him behind bars for life. The day self from the team,” says the teammate. ingly violent descent into the world of crime, after his arrest, users visiting Silk Road’s Later that year, on November 6, 2013, which prosecutors allege led him to spend Tor address were greeted with a message someone the FBI refers to as DPR2, or Dread several hundred thousand dollars in Bit- from the Department of Justice and the Pirate Roberts 2, launched Silk Road 2.0. It coins on contract killings to protect his crimi- FBI: “This hidden site has been seized.” had been less than a month since Ulbricht’s nal enterprise. (None of the hits appear to arrest. When the site went live, it displayed a have been carried out.) Allowing gun sales II message boldly mocking the one authorities on Silk Road also aligned with the libertarian On a quiet Sunday morning last March, had left after seizing the original Silk Road: beliefs prevalent on the site, values core to Blake ­Benthall woke before sunrise at his “This hidden site has risen again.” 116 Ulbricht’s mission to create a ­regulation-free home in San Francisco’s Mission district. It A week later, ­Benthall joined Silk Road 2.0 as an administrator under the user was well liked around their offices, situated name Defcon. Over the next month he just off Turk Street in one of the Tenderloin’s would be given two opportunities to step most crime-plagued areas, where drug deal- off the path he had chosen: First, he landed­ ers conduct business in plain sight. ­Benthall, a software engineer’s dream job at Elon living just a couple of miles south of the min- Musk’s SpaceX, where he would jokingly istry, was surreptitiously facilitating the sale tell friends he was a rocket scientist. Then, of $8 million in illicit goods each month, gen- on December 20, three other Silk Road 1.0 erating at least $400,000 in monthly commis- administrators were arrested. ­Defcon post- sions. Drugs accounted for the majority of ed an urgent message to users on the site’s the sales, bought and sold among Silk Road forums later that day. “Three of our dear 2.0’s cloistered community of 150,000 active friends were arrested in connection to their users, who, by the grace of ­Benthall, lived Silk Road 1.0 activities,” he wrote. “They above the fray, a long way from Turk Street. did not have access to anything which would At City Impact ­Benthall met his girl- compromise the marketplace. We are watch- friend, Stephie, who worked there as an in- ing everything very closely regardless.” tern. In spring 2014, the couple announced DPR2 saw the writing on the wall and their relationship by sharing a photo of a abandoned the site he had ­created. ­Benthall romantic walk on the beach on Facebook. stayed, and on December 28 he announced Some of ­Benthall’s friends were surprised: he would be taking over with a stump “A girl!!!! OMG Blake ­Benthall,” one wrote; speech to assure users they were in good “Get a room,” wrote another. The couple hands. “I intend to prove to you that lead- had been close well before ­Benthall took on ing this movement forward is my top prior- his Defcon alter ego, but as he expanded ity in life,” he wrote, “and that I will pour the site’s reach, the two grew closer. any time and energy necessary into ensur- In just a handful of years, the young ing its success. I’m ready to fight right here software engineer had conquered a town alongside you.” He soon quit his dream job known to run through ambitious techies at SpaceX. In the dark corners of the deep like Hollywood runs through aspiring web, he had found a new frontier to explore. young stars. And though he told a neigh- The marketplace quickly picked up where bor he often missed his mother, he was the original Silk Road had left off. On Janu- able to maintain his Christian faith and ary 14, 2014, just a few weeks after assum- find someone to share it with. Last Au - ing control of the site, Defcon announced gust, Blake hiked the Washington coast he would personally decide how much com- with Stephie and his parents, Larry and mission to charge on each sale. He justified Sharon ­­Benthall. Together they posed for the commission scale, which ranged from photos among evergreens lining steep cliffs four to eight percent, by talking about the overlooking the Pacific. ­Benthall appears risks he and his staff were taking on. “I serene and unworried alongside his girl- have no doubt that we have the highest traf- friend as they pose in front of Mount Rain- fic,” he wrote, referencing the site’s grow- ier. A few days earlier, on July 30, he had ing popularity. “Purchases are going up, transferred Silk Road 2.0 onto a new hid- vendors are going up—and alongside this, den server, according to court documents. the amount of personal risk staff is taking But federal agents had been watching is exponentially going up. The bigger we ­Benthall for months. The FBI’s undercov- become, the more resources agencies are er operative had the kind of access neces- willing to spend on hunting us.” sary to explore the site’s architecture and But at that point the hunt had been going interacted with ­Benthall regularly. While a on far longer than ­Benthall could have imag- case was built from the inside, other agents ined. Even before ­Benthall joined the site, an tracked his day-to-day movements. They undercover federal agent had been hired to watched as he placed a $70,000 down pay- moderate its discussion forums. With almost ment on a Tesla Model S using ­­Bitcoins—a total access to its inner workings, the insider rare indulgence for ­Benthall, who had to helped the FBI locate one of the site’s hid- rent his elderly neighbor’s parking space den servers abroad. In May 2014 foreign for the $127,000 car. “He was a very sweet authorities made a copy of the server and boy, and so polite,” she tells me. “Always of- delivered it to federal agents in the U.S. fering me rides, always coming around to Benthall, like Ulbricht, grew up in Texas. talk.” Like the rest of ­Benthall’s secret life, He was raised in a Christian household in a the Tesla went basically unnoticed. “It’s not large single-story home in Houston. In 2009 an unusual car to see in San Francisco,” the promising young programmer dropped one of ­Benthall’s friends tells me. Anoth- out of his sophomore year of college in er says he heard ­Benthall paid for it with Florida and took a ­computer-programming money he’d earned doing consulting work. position at RPX Corporation in San Fran- On November 5, as ­Benthall pulled the cisco’s financial district. The Texas boy did car out of his neighbor’s driveway, he was not stand out in the city where a generation swarmed by 20 FBI agents who approached of precocious programmers had flocked the vehicle with guns drawn. They took him to find work that matched their ambitions. into custody without incident. According to Although ­Benthall kept his religious beliefs prosecutors, he quickly admitted to every- quiet around friends in the tech commu- thing he’d been accused of in the federal in- nity, he clung to his Christian values. He dictment outlining ­Defcon’s crimes, which volunteered at San Francisco City Impact, a included charges of computer hacking, ministry dedicated to helping the poor and money laundering and narcotics trafficking. homeless in the Tenderloin district, the city’s In the months after ­Benthall’s arrest, his skid row. The ministry’s human resources girlfriend’s Facebook cover photo changed director, Hayley Duerstock, says ­Benthall to display a image of the couple embracing, 117 with a heart covering their faces and the abounded that police were able to follow a in the immediate aftermath of Operation word faith typed over it. Above the image was trail of Bitcoins from illegal deep-web trans- Onymous, “but we’re working at it, trying a reference to Hebrews 4:16. “Let us there- actions to real-world payments, such as the sophisticated attacks and very stupid ones. fore come boldly unto the throne of grace,” one Benthall­ had made for his Tesla. You never know where you might have a the passage reads, “that we may obtain mer- The scope of Operation Onymous, how- weakness. Sometimes, people get lucky.” cy, and find grace to help in time of need.” ever, was broader than the illicit sites it confis- Months later, Lewman remains convinced cated, and its implications extend beyond cy- that Operation Onymous was a product III bercrime into the realms of free speech and of luck. “Tor is still safe,” he tells me in Two days later, it became clear that Silk government surveillance (even if it requires a January, a reassurance no one would have Road 2.0 wasn’t the only corner of the dictionary to ­realize—onymous­ is an antonym thought to ask for prior to Onymous, when deep web authorities had been monitor- of anonymous). Peter Carr, a spokesperson for Tor was still considered ­unbreakable—even m ing. On November 7, while ­­Benthall ate the Department of Justice, says the full roster by the National Security Agency, according his second breakfast in federal custody, of seized websites ­reaches “well beyond the to documents leaked by Edward Snowden. law-enforcement­ agencies in the U.S. and 27 identified” but it would take time for the Ironically, the U.S. government under- abroad executed coordinated raids in 16 various law-enforcement­ agencies involved stands exactly how effective Tor is as a tool countries as part of Operation Onymous, to assess the extent of Operation Onymous. for secure browsing and communication, an effort to seize a number of hidden sites Until the government shows its hand, it’s because the government created it. In the operating on Tor. It was an unprecedented hard to say definitively whether Tor has been mid-1990s, “the onion router” method of move to curb crime on the deep web, as well cracked or not. What is known, however, is online anonymity was developed at the U.S. as a statement about the kinds of sites au- that Operation Onymous relied ­heavily on Naval Research Laboratory. Its name follows thorities planned to target. The sweep re- informants, undercover agents and detective from the logic behind its core functionality, sulted in 17 arrests and the seizure of drugs, legwork to bring down its targets. which places multiple layers of connection cash and about a million dollars in Bitcoins. At Tor Project’s modest Cambridge, Mas- between users and the sites they access. The Authorities announced the confiscation of sachusetts headquarters, the November 7 Tor browser thwarts electronic surveillance 27 hidden sites—most of them illicit mar- raids came as a most unwelcome surprise. and tracking by sending user page requests kets similar to Silk Road 2.0—as well as a Tor’s 30 employees had nothing to do with through three randomly selected relays in number of servers that hosted them. illegal sites such as Silk Road, but they decid- its network of 6,000 ­volunteer-run ­servers. Tremors immediately shot through on- ed to scrap their weekend plans for an all- These relays act as ­layers—hence the line communities that had a stake in keeping hands-on-deck effort to uncover how their ­onion—that protect users from direct con- the deep web anonymous. Privacy and free network may have been compromised. For nections with hidden sites. When someone speech advocates, journalists, Bitcoin en- days they attacked their own code to expose in Nebraska visits a hidden site, his page re- thusiasts, political dissidents and criminals vulnerabilities law enforcement may have quest might first be routed through a server all struggled to make sense of how sites de- exploited to crack Tor. They found nothing. in Vermont, where his IP address could the- signed to be anonymous and servers meant Leading the effort was Tor’s executive oretically be identified; then it would filter to be hidden had been found. Some were director, Andrew Lewman, who knows pre- through a second relay, where neither pre- hopeful that law enforcement had relied on cisely how vulnerable citizens can be online. vious IP address could be identified; finally, informants, insiders and holes in site admin- Once the vice president of engineering at it would reach a third server, which sends istration to carry out their raids, while others a major online marketing company, he it on to its ­destination—the only part of the worried that fissures had been discovered helped design the systems that originally puzzle the final relay can see. The whole in Tor’s code and encryption once thought eroded privacy on the internet. “It doesn’t process is wrapped in encryption, making it unbreakable had been cracked. Speculation seem to be bugs in our code,” he told me 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 creat- ing the competition that birthed the self-­ driving car. The Tor Project, a nonprofit group, took up the cause on behalf of civil- ians a few years later, releasing the first ver- sion 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 demo- cratic 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 Bitcoin, which gave Silk Road and similar sites the means to monetize their operations. Today, Tor’s public image is decidedly more com- plicated, and not just because of Silk Road. Operation Onymous’s big trophies in- cluded Silk Road 2.0 and other illicit mar- kets. But the raid also saw noncommercial sites built for the Tor network targeted by law enforcement for the first time. Doxbin, 118 “Marvin is in government mismanagement.” a repository for posting names, addresses and Social Security numbers for the ben- It was akin to filing suit against Google over ing their own lines when it comes to dealing efit of identity thieves and fraudsters, was an illegal image in your search results. Lew- with the deep web. In 2009 several thousand one of several sites closed without a clear man emphasizes that the sole purpose of users were logging on with the Tor browser legal basis. Pink Meth, an extreme exam- the Tor Project is to facilitate free speech; each day in mainland China. Then, in early ple of a website genre called revenge porn, Van Dyke, widely ridiculed online for mis- 2010, the traffic suddenly dropped to almost was also shut down. At Pink Meth, hacked understanding Tor and its potential liabil- nothing and has remained that way since. nude photographs of women from around ity, soon dropped the organization from his the world were posted alongside their per- suit. “I would compare Tor to a handgun,” IV sonal information, often including links to the conservative Texan says. “It can be used FBI special agent Vincent D’Agostino spent Facebook, Twitter and ­LinkedIn profiles. by good people to do good things, but in the the summer of 2010 working to put away In some cases, e-mail addresses and other wrong hands it can cause terrible harm.” a prominent underboss from New York’s contact information were included as well. On the morning of the Onymous raids, ­Colombo crime family. John “Sonny” Franz- Shelby Conklin, a 22-year-old recent col- police in the Netherlands seized three ese Sr. was 93 years old when his racketeering lege graduate from northern Texas, was ­volunteer-run Tor servers. How police un- trial began that June, but old age hadn’t made one of the site’s victims. Conklin’s photos covered the ­relays—and the legal basis on him sentimental: As Franzese looked on from were stolen from a hacked Photobucket­ ac- which they were seized—remains­ a mystery. his wheelchair, D’Agostino told the court that count, according to her attorney, Jason Van Lewman says the Tor Project collaborates the Mob boss had ordered a hit on his own Dyke, who says she had to delay pursuing with law-­enforcement authorities to help son after learning he’d worn a wire for the a career until she FBI. What Franzese could be sure the im- hadn’t known was ages wouldn’t turn that D’Agostino had up in a background more than one well- check. Most photos placed informant in that end up as re- the Colombo syndi- venge porn are made cate. When Sonny in the context of a re- 3 CIGARS had asked Gaetano lationship and then “Guy” Fatato to kill leaked by the man John Franzese Jr., after it sours—“and $ the would-be hit it’s always the man,” man had been work- Van Dyke says—but only ing with the FBI for Conklin’s case was 15 months. Eventu- unique in that her 5 ally Fatato would photos were stolen $ spend two full years by strangers from a 44.00 helping D’Agostino private online stor- value collect more than age account. 1,000 hours of tape-­ Just days after Op- recorded conver- eration Onymous sations between took down the site, Sonny and his co-­ Conklin walked into a conspirators. Texas courtroom and As part of a special won a default judg- FBI team called C-38, ment against Pink D’Agostino worked Meth in a civil case cases that, accord- that began early last ing to The Washington summer. She doesn’t Enter full web address for offer Post, “decimated” the expect to see any of Colombo crime fam- the ­million-dollar Cigar.com/CGSA502 ily and “severely dis- judgment. “To this Or call 800.357.9800 rupted” the Bonanno day we don’t know Mention CGSA502 • Offer expires 6/15/15 family, one of four the identity of a single other syndicates that person associated with *Please add $2.99 s/h. Taxes on orders shipped outside of PA are the responsibility of the once waged war on purchaser; PA residents add 6% tax. Available to new customers only. One per customer. From Pink Meth,” Van Dyke time to time substitutions may occur. We only sell our products to adults who meet legal age the streets of New tells me, a sign that requirements to purchase tobacco products. York City. With the The Home for Cigar Enthusiasts 1911 Spillman Drive | Dept. #26 | Bethlehem, PA 18015 without informants, Mob all but destroyed, the government’s abil- D’Agostino took on a ity to police the deep web may still be limited.­ them understand the deep web so they can new challenge as his career entered its sec- For some activists, there are concerns enforce existing laws. Lewman also works ond decade: He joined the FBI’s cybercrimes­ that the challenges of policing a digital with women who have been victimized by unit, where he would hunt hackers, online realm like the deep web, where users are sites like Pink Meth, and while he is happy fraudsters and, eventually, Blake Benthall.­­ anonymous and sites are often legally am- to see these sites leave the deep web, watch- ­Benthall’s comments in the Silk Road biguous, could push police to bend legal ing them be seized quietly and with no le- 2.0 forums, posted under the Defcon mon- frameworks in the name of justice. Those gal ­basis raises fears about what might come iker, reveal his idealism. He spoke of the concerns have been exacerbated by the fact next. Lewman worries that more lines will site as an experiment in freedom, a place of that police agencies have yet to publicly ac- be crossed as police adapt to technologies refuge against unnamed “oppressors.” But knowledge their seizure of noncommercial that strain already overburdened depart- behind his rhetoric was a business that had Tor sites such as Pink Meth and Doxbin or ments and agencies, and that precedents will more in common with the Mob than with a to explain which laws the sites violated. be set that can’t be recalled. “I worry about tech start-up. He didn’t solicit murder, but Conklin’s lawsuit also underscores just legislating technology,” he says. “If you leg- ­Benthall made millions offering protection how much public confusion remains about islate Tor, that can create real problems, be- to the vast network of criminal enterprises the deep web. When Van Dyke initially cause once the technology moves on, you’re that thrived in his marketplace. And de- brought suit against Pink Meth, he listed left with laws that no longer fit the world you spite the technology involved, ­Benthall’s Tor as a defendant, believing the organiza- live in. We have to be able to adapt.” was a business of relationships, one of tion existed solely to facilitate online crime. Around the world, governments are draw- which would be his undoing. 119 It was misplaced trust in an undercover eral courthouse. Some held signs that the web for its Tor address, which led to an ­agent—a human failure, one no firewall or read WEB HOSTING IS NOT A CRIME! Another account on ­BitcoinTalk.com that advertised encryption software can protect ­against— obscured his face with a black T-shirt Silk Road’s earliest iteration. Later, a job post- that gave the FBI everything it needed worn as a makeshift balaclava and held a ing for a web developer asked ­interested can- to tie ­Benthall to Defcon and land him in small placard emblazoned with THE CHOSEN didates to e-mail ­[email protected]. In federal custody. ­Benthall failed techno- ONE and a Bitcoin logo. Inside the stately court, prosecutors used selfies Ulbricht had logically as well. On January 5, 2014, in a courthouse, the chosen one himself, Ross sent from the account to prove it was his. forum post, he urged Silk Road 2.0 users ­Ulbricht, stood trial. His attorney claimed ­Ulbricht’s defense relied on the idea that he to take all necessary precautions when it that Ulbricht created Silk Road as a radical had indeed run the site at one point, but soon came to security and anonymity. “We are economic experiment that he quickly aban- a different Dread Pirate Roberts took over, the biggest market on the darknet at this doned, only to be reeled into a life of crime who truly ran Silk Road. But with hundreds m point,” he wrote. “We are in a position to by tech-savvy drug dealers. The following of pages of evidence directly tying Ulbricht to teach an incredibly valuable life skill to this week, testimony from Special Agent Tom Silk Road and his DPR handle, and a weak buyer community: always encrypt.” It was ­Kiernan cast serious doubt on those claims. defensive strategy in court, on February 4 good advice, but as any good hacker will After Ulbricht was arrested, Kiernan Ulbricht was found guilty of all seven counts tell you, digital security tools can’t protect went to work on Ulbricht’s Samsung 700z with which he’d been charged. users from their own bad habits. laptop. For three hours he took photo- Blake ­Benthall seems to have chosen a ­Benthall’s included inconsistent use of the graphs of Ulbricht’s browser history and different path. On November 21—less than very encryption methods that kept deep- explored the hard drive; afterward, an- three weeks after his arrest in San Francisco, web sites hidden from authorities in the first other agent copied its contents. It would after which prosecutors had labeled him an place. While administrating Silk Road 2.0, prove to be better than a smoking gun. extreme flight risk—Benthall­ was released ­Benthall used Tor and took appropriate Spreadsheets of Silk Road finances and from the custody of the Federal Bureau of anonymity measures, but he was lazy about years’ worth of Tor chat logs gave the jury Prisons. Court filings from December suggest security when it counted. When authorities a small taste of what Kiernan had gleaned. a reason behind the change of heart, with took Silk Road 2.0’s servers off-line to copy Documents outlined the banal minutiae of references to discussions between prosecu- them, it caused an outage, which ­­Benthall a drug empire, including payroll sheets and tion and defense attorneys about “a possible handled the way one might deal with an un- notes on staff promotions. Like any busi- disposition of this case.” In other words, the known phone-bill charge: He complained two sides are negotiating. ­Benthall’s current using support tickets sent from ordinary whereabouts are unknown, and his lawyers web browsers easily matched to his laptop. and family have not returned calls for com- He also accessed ­customer-­support portals ment. If he decides to cooperate with author- for Silk Road 2.0’s server over the internet, ities and help lead them to other arrests, he using wi-fi in a hotel room he’d booked un- “Even I know may find some measure of the mercy men- der his own name. There are a number of tioned in Hebrews 4:16. In the eyes of Silk less obvious ways people hosting hidden Road’s true believers, however, it is ­Ulbricht sites can leave themselves vulnerable to de- to cover my who went boldly unto the throne of grace. tection, but few suspected Silk Road 2.0’s Perhaps the most damning evidence in- operator would be caught playing so fast tracks better troduced in Ulbricht’s trial was a personal and loose with his own digital security. diary he kept on his laptop, dating back to For ­Benthall’s friends in the tech com- than he did,” 2010. He detailed his struggle to hold a job, munity, the only thing more shocking than his failed efforts at an early start-up, his rocky his second life as Defcon was how many relationship with his girlfriend. In an effort commonsense deep-web rules he broke. says a friend of to create interest in the site, he wrote about “I’m no criminal mastermind,” one tells growing several kilograms of psychedelic me, “but even I know to cover my tracks Benthall’s. mushrooms to sell on it before he’d even set better than he did.” up a server. “In 2011, I am creating a year of As quickly as Silk Road 2.0 emerged to prosperity and power beyond what I have replace Ulbricht’s original drug bazaar, ever experienced before,” he wrote. “Silk some sites that had been seized in Opera- Road is going to become a phenomenon.” tion Onymous returned to the deep web. nessman, Ulbricht kept scanned copies of The journal chronicled his thoughts dur- Doxbin was restored to full operation just his employees’ ID cards on file. ing the site’s growth—its first mainstream one week after the Onymous raids con- During the trial, Assistant U.S. Attorney press coverage, mistakes made and lessons cluded, and on January 11 a new hidden Timothy Howard read chat logs from a 2013 learned, and growing paranoia amid back- site called Silk Road Reloaded launched, conversation in which Ulbricht assured a Silk breaking work to administer his empire. bringing with it a renewed set of security Road seller that authorities didn’t have the He wrote about feeling guilty for the half- challenges for law enforcement. Accessible technological facility to get their hands on truths he perpetuated to hide Silk Road only with a new deep-web browser called the kind of unencrypted information they from his closest friends. In his last entry, IP2, Silk Road’s latest iteration requires the would need to build a case against the site. from New Year’s Day 2012, he described a reconfiguration of one’s computer to work. “Put yourself in the shoes of a prosecutor day at the beach: “I imagine that some day Speculation abounds that it is even more trying to build a case against you,” he wrote. I may have a story written about my life, secure than Tor. As an added layer of secu- “When you look at the chance of us getting and it would be good to have a detailed rity, Silk Road Reloaded accepts an alterna- caught, it’s incredibly small.” But Ulbricht account of it.” He played paddleball, sun- tive cryptocurrency, which it then converts failed to put himself in the shoes of Vin- bathed with his friends and turned down into Bitcoins on its own, making transac- cent D’Agostino and other agents like him, invitations to warehouse parties and camp- tions even more difficult to trace. agents who don’t need to rely on technology ing trips for fear of spending too much time Lewman, for his part, is leading his to build their cases. Instead, Ulbricht built a away from the site. If he weren’t at the helm organization in the ongoing testing and case against himself on his laptop in the form of one of the internet’s largest criminal en- strengthening of Tor’s code. “The compa- of meticulous records of every crime he’d terprises, he’d be any other 20-something nies that made armored vehicles used in committed. All the agents at Glen Park Li- in San Francisco. “I’ve been thinking a Iraq built them to withstand bullets,” he brary needed to do was reach out and grab it. bunch about what is next for me,” he con- says by way of comparison. “But then they In other cases, detective work as unso- cluded, contemplating moving to Thailand had to outfit them to resist improvised ex- phisticated as a Google search led investiga- or Australia. “I need to find a place I can plosive devices as well.” tors to their suspects. In court, IRS Special work from. Cheap and off the beaten path.” On January 13 a dozen protesters gath- Agent Gary Alford testified that he originally 120 ered outside downtown Manhattan’s fed- tied Ulbricht to his drug empire by searching b