Silk Roads

by cominsitu

Chronicpain

“I imagine that someday I may have a story written about my life and it would be good to have a detailed account of it.” —home/frosty/documents/journal/2012/q1/january/week1

THE POSTMAN ONLY rang once. Curtis Green was at home, greeting the morning with 64 ounces of Coca-Cola and powdered mini doughnuts. Fingers frosted synthetic white, he was startled to hear someone at the door. It was 11 am, and surprise visits were uncommon at his modest house in Spanish Fork, Utah, a high-desert hamlet in the shadow of the Wasatch Mountains. Green ambled over, adjusting his camouflage fanny pack. At 47 his body was already failing him: He was overweight, with four herniated discs, a bum knee, and gleaming white dental implants. To get around he sometimes borrowed his wife’s pink cane. Green waddled to the door, his two Chihuahuas, Max and Sammy, following attentively.

He peeked through the front window and caught a glimpse of the postman hurrying off. The guy was wearing a US Postal Service jacket, but with sneakers and jeans. Weird, Green thought. Also odd was a van Green noticed across the street, one he’d never seen before: white, with no logos or rear windows.

Green opened the door. It was winter, a day of high clouds and low sun. A pale haze washed out the white-tipped Spanish Fork Peak rising above the valley. Green looked down. On the porch sat a Priority box—about Bible-sized. His little dogs watched him pick up the mystery package. It was heavy, had no return address, and bore a postmark from Maryland.

Green considered the package and then took it into his kitchen, where he tore it open with scissors, sending up a plume of white powder that covered his face and numbed his tongue. Just then the front door burst open, knocked off its hinges by a SWAT team wielding a battering ram. Quickly the house was flooded by cops in riot gear and black masks, weapons at the ready. There was Green, covered in cocaine and flanked by two Chihuahuas. “On the floor!” someone yelled. Green dropped the package where he stood. When he tried to comfort his pups, a dozen guns took aim: “Keep your hands where we can see them!”

Officers cuffed Green on the floor while fending off Max, the older Chihuahua, who bared his tiny fangs and bit at their shoelaces. Splayed out on the carpet, Green was eye level with dozens of boots: A large tactical team—SWAT and DEA agents—fanned out through the house. He could hear things crashing, some officers yelling, others whispering to each other. He looked at the busted door and thought, Man, that thing was unlocked. On the living room wall hung family photos—his wife, Tonya, their two daughters, and a grandson—smiling brightly above Green, lying amid $27,000 worth of premium flake. (The package was stamped with a red dragon, the symbol for high-quality Peruvian.) Over the whole scene was a needlepoint that said: if i had known you were coming, i would have cleaned up! Excited by the company, little Max stopped shaking just long enough to crap right in the living room.

Which is why Green found himself surrounded by an interagency task force. He had been hired by Dread Pirate Roberts, the mysterious figure at the center of Silk Road. DPR, as he was often called, was the proprietor of the site and the visionary leader of its growing community. His relatively frictionless drug market was a serious challenge to law enforcement, who still had no idea who he or she was—or even if DPR was a single person at all. For over a year, agents from the DEA, the FBI, Homeland Security, the IRS, the Secret Service, and US Postal Inspection had been trying to infiltrate the organization’s inner circle. This bust of Green and his Chihuahuas in the frozen Utah desert was their first notable success.

The Feds got Green on his feet. They had a lot of questions, starting with why he had $23,000 cash in his fanny pack and who was on the other end of the encrypted chat dialogs on his computer. Green said, improbably, that the money was his tax return. He also asked for his pain medication. Instead they escorted him to the door and into a squad car, informing him that he’d be booked for possession of 1,092 grams of cocaine with intent to distribute.

“Don’t take me to jail,” Green pleaded. “He knows everything about me.”

Later, under interrogation, Green told the skeptical agents that to charge him and make his name public was a potential death sentence. Dread Pirate Roberts was dangerous, he said: “This guy’s got millions. He could have me killed.”

 

The fact was, Green wasn’t just your average Mormon grandpa. Over the past few months he had been handling customer service for the massive online enterprise called Silk Road. It was like a clandestine eBay, a digital marketplace for illicit trade, mostly drugs. Green, under the handle Chronicpain, had parlayed his extensive personal narcotics knowledge—he’d been on pain meds for years—into a paying gig working for the site. Silk Road was hidden in the so-called dark web, a part of the Internet that’s invisible to search engines like Google. To access Silk Road you needed special cryptographic software. Combining an anonymous interface with traceless payments in the digital currency bitcoin, the site allowed thousands of drug dealers and nearly 1 million eager worldwide customers to find each other—and their drugs of choice—in the familiar realm of ecommerce. For a brief time, from 2011 to 2013, it was a wild success. In that relatively short span, Silk Road managed to rack up (depending on how you count) more than $1 billion in sales.

 

Rossman

ROSS ULBRICHT WAS deep into his regular drum circle when he spotted her. As Ross slapped the hide on his djembe, a West African drum, Julia Vie sat across the circle. She had a head full of curls, light brown skin, and dark brown eyes. The drum circle was assembled on a lawn at Penn State, where in 2008 Ross was working toward a master’s degree in materials science and engineering. Julia was 18, a free-spirited freshman, and when she noticed Ross she felt a powerful attraction. Not long after, Julia visited Ross’ campus office, where they couldn’t help but kiss and fall into a carnal heap on the floor.

Both were smitten. Ross studied crystallography, working on thin-film growth. One day he made a large, flat blue crystal, affixed it to a ring, and gave it to Julia. She had no idea how her boyfriend could make a crystal, but she knew she was in love.

Ross had grown up in Austin, Texas, and had always been smart and charming. He’d been the kind of kid who was an Eagle Scout—and let his friends give him a mohawk on a whim. He was raised in a tight family. They’d spend summers in Costa Rica; Ross’ parents had built a series of rustic, solar-powered bamboo houses there, near an isolated point break where Ross learned to surf. In high school, “Rossman,” as friends called him, drove an old Volvo, smoked plenty of pot, and still got a 1460 on his SATs. To friends, Ross was carefree but also caring.

Ross earned a scholarship to the University of Texas at Dallas and majored in physics. From there he landed a graduate scholarship at Penn State, where he excelled as usual. But he wasn’t happy with the drudgery of lab research. Since college he’d been exploring psychedelics and reading Eastern philosophy. At Penn State, Ross talked openly about switching fields. He posted online about his disenchantment with science—and his new interest in economics.

He’d come to see taxation and government as a form of coercion, enforced by the state’s monopoly on violence. His thinking was heavily influenced by Austrian economist Ludwig von Mises, a totem of the modern American libertarian orthodoxy. According to von Mises, a citizen must have economic freedom to be politically or morally free. And Ross wanted to be free.

When he finished his master’s in 2009, he moved back to Austin and bought Julia a plane ticket to join him. She left school, and they got a cheap apartment together. It was cramped, but they were young and dreamy. Both imagined they might get married.

In his spare time Ross read, hiked, improved his yoga, and, as Julia fondly recalls, had “lots and lots of great sex.” But they also argued, about politics (she was a Democrat), money (what he called “frugal,” she called “cheap”), and their social life (she partied more than he did). Their relationship turned stormy, with frequent breakups. In the summer of 2010, they split up yet again. He was heartbroken, later telling a woman he met on OkCupid how he’d recently been in love and was trying to get over it.

Ross was adrift. “I went through a lot over the year in my personal relationships,” he wrote in a journal on his computer, a kind of self-assessment of life goals. “I had left my promising career as a scientist to be an investment adviser and entrepreneur and came up empty-handed.” Ross felt ashamed, but not long afterward Palmertree got a job in Dallas, leaving Good Wagon to Ross. For years, all he’d wanted was to be in charge of something. Now he was.

In the Good Wagon warehouse, Ross oversaw five part-time college students sorting, logging, and organizing the 50,000 books on shelves he built himself. That December was Good Wagon’s best month, clearing 10 grand.

But by the end of 2010, the new CEO of Good Wagon was looking beyond the book business. During his forays into trading, Ross had discovered bitcoin, the digital cryptocurrency. The value of bitcoin—based only on market factors, unattached to any central bank—aligned with his advancing libertarian philosophy. On his LinkedIn page, Ross wrote that he wanted to “use economic theory as a means to abolish the use of coercion and aggression amongst mankind.”

Ross tried day trading, but it didn’t go well. He started a videogame company. That failed too. The setbacks were devastating. He didn’t want to be trying; he wanted to be doing. During this time, his downstairs neighbor, Donny Palmertree, invited Ross to work with him on Good Wagon Books, a business that collected used books and sold them in digital storefronts like Amazon and Books-A-Million. Ross built Good Wagon’s website, learned inventory management, and wrote a custom script that determined a book’s price based on its Amazon ranking.

To that end Ross had a flash of insight. “The idea,” he wrote in his journal, “was to create a website where people could buy anything anonymously, with no trail whatsoever that could lead back to them.” He wrote that he’d “been studying the technology for a while but needed a business model and strategy.”

Like most libertarians, Ross believed that drug use was a personal choice. And like all people paying attention, he observed that the war on drugs was a complete failure. The natural merchandise for his new enterprise would be drugs. “I was calling it Underground Brokers,” Ross wrote, “but eventually settled on Silk Road.”

Ever the capable scientist, Ross decided to cultivate his own psilocybin mushrooms as a starter product. He was spending time with Julia again, while struggling with programming his site and still running Good Wagon.

Then, one night in early 2011, Good Wagon collapsed. In the literal sense. Ross was working late, alone in the warehouse, when he heard an enormous crash—the sound of the library falling apart. He’d carefully designed the entire system but had somehow forgotten two vital screws, the ones that held it all together; the shelves came down, every single one, like dominoes.

When Ross broke the news to Palmertree, he also admitted that his heart wasn’t in Good Wagon anymore. They agreed to close the company, with no hard feelings. He told Palmertree that he already had a new business idea—“something really big.”

Silk Road went live in mid-January 2011. A few days later came the first sale. Then more. Ross eventually sold all 10 pounds of his mushrooms, but other vendors started joining. He was handling all the transactions by hand, which was time-consuming but exhilarating. It wasn’t long before enough vendors and users made it a functioning, growing marketplace.

Just before the launch, facing a new year and a blank slate, Ross had resolved to change his life. “In 2011,” he wrote to himself, “I am creating a year of prosperity and power beyond what I have ever experienced before. Silk Road is going to become a phenomenon and at least one person will tell me about it, unknowing that I was its creator.”

Force

SPECIAL AGENT CARL Mark Force IV was half-asleep when the postal inspector started talking about something weird in the parcel sorters. “Just wanna let everybody know about this,” the inspector said, delivering his brief to a conference room full of bored law enforcement personnel. “We are having problems with drugs coming through the mail.”

Force was a Baltimore-based DEA agent, and he was at a regional interagency meeting, a periodic intel show-and-tell with analysts from the FBI, the DEA, the IRS, and Homeland Security. “It’s coming from an underground drug site,” the inspector said, “called Silk Road.”

Force sat up. This was the kind of thing he was looking for. He had burned out on the grind of arresting street dealers. At 6 feet and 200 pounds, Force was an athletic guy, and coming up through the agency he’d loved the physical thrill of bursting through a door at 6 am in Doc Martens and a tactical vest, clearing some broke-down row house on some broke-down block and catching some dealer in the bathroom, cuffing the guy before he could wipe his ass. But after countless raids, the adrenaline had worn off. And in the grand scheme of things, who cared about confiscating a few grams? He was pushing 50 and still on the federal payroll in a regional office. That’s when you want to find a big case and get out. And so he went looking for leads in meetings like this, which were mostly yawners—until now.

By the time Force heard about Silk Road, it had been around nearly a year. The site was modeled, sensibly, on Amazon and eBay. And that’s what it looked like: a well-organized community marketplace, complete with profiles, listings, and transaction reviews. Everything was anonymous, and shipments often went through the regular old postal service. No need for fake names—you put your real address, and if any one asks, you just say you didn’t order all that heroin!

Then there were the prescription meds, everything from Oxycontin and Xanax to Fentanyl and Dilaudid. Silk Road’s product descriptions and user ratings amounted to an encyclopedic information source. Cantfeelmyface said one product “has a nice shine” and provides “a rush of euphoria and confidence.” Ivory’s review of some crystal MDMA observed that it had “a nice fizz and wisp of smoke =].” The reviews and community standards enforced excellent value and customer service on Silk Road, which brought more users, increasing its reputation further—until Silk Road became the premier destination for digital drug sales.

Law enforcement was caught with its tactical pants down. Various agencies had sniffed around Silk Road in the summer of 2011 but gotten nowhere. Force saw potential but didn’t even know where to begin.

Months later, in January 2012, he got some good news from his supervisor. Homeland Security was assembling a task force for a full-on Silk Road case. “You want in?” his boss asked.

Before he knew it, Force was at a Silk Road summit, where he and 40 other agents picked through doughnut boxes and watched PowerPoint presentations filled with technical information about nodes and TCP/IP layers. Most of the agents’ eyes glazed over, but, yes, Force wanted in.

The task force that formed to take on Silk Road—Operation Marco Polo—was based out of the Baltimore Homeland Security Investigations office. Another agent showed Force how to navigate Silk Road. He quickly saw that it had a vocal mastermind, the revered figure known as Dread Pirate Roberts. It was a clever touch, borrowing the name from The Princess Bride, in which the pirate was a mythical character, inhabited by the wearer of the mask. The idea of a malleable but enduring identity only added to Silk Road’s enigmatic appeal. Force was intrigued. Whoever wore this digital mask sat atop a burgeoning empire. Force told his boss that Silk Road was a “target of opportunity.” But he was unskilled at computers, and he didn’t know anything about bitcoin. So he decided to learn.

 

Silk Road’s “Seller’s Guide” had helpful instructions on how to vacuum-seal or otherwise hide drugs to evade electronic sensors or canine olfactories. Most shipments made it to happy customers. That the small percentage of intercepted Silk Road packages represented an uptick spoke to the quickly rising volume of the site’s trade, a vast pharmacopeia covering dozens of categories with 13,000 listings. It was a colorful smorgasbord for every type of connoisseur: fish­scale Colombian cocaine, Afghan No. 4 heroin, strawberry LSD, Caramello hash, Mercury’s Famous uncut cocaine flakes, Mario Invincibility Star XTC, white Mitsubishi MDMA, a black tar heroin called the Devil’s Licorice.

Onion Peeler

HECTOR XAVIER MONSEGUR was an unusual visitor to the New York FBI office. Then again, Monsegur was not really a visitor. It was past 1 am one night in the spring of 2011, and he was being led to the back of the empty bullpen by Chris Tarbell, a young agent who had arrested Monsegur earlier that night in the Jacob Riis Houses on the Lower East Side. Monsegur was an enormous Puerto Rican, ears studded with diamonds, who grew up in the projects. He was also Sabu, a cofounder of LulzSec, the elite group of hackers responsible for electronically attacking dozens of corporate and government targets like News Corp. and the CIA. Sabu was the most high-profile member of Anonymous, the “hacktivist” political collective. Tarbell had managed to follow a blind lead from the FBI’s public hotline to Sabu and reel him into the FBI as an informant. It was a remarkable score for Tarbell, especially since he was still a rookie.

Tarbell had always had the cop in him, even when his parents thought he was going to be a doctor. In college he was a powerlifter, an unusual sight at James Madison University, a preppy school in the Shenandoah Valley. He already looked like a cop: big, with a short coif on top of that baby face. By the time Tarbell finished college, he sensed where policing was headed and got a master’s in computer science. He didn’t understand programming at first. But he did understand that this was the future, so he paced himself, stuck with it, and came out the other side as a computer forensics expert, working as a civilian for the FBI.

Tarbell spent four years traveling the world with global forensics, tracking down terrorists, child pornographers, and botnets. He showed a talent for uncovering digital trails. He thought about how the virtual realm seemed like magic, a secret world, poorly understood; and like all magical realms, it was full of charlatans and practitioners of dark arts. Few could decipher those secrets, and Tarbell liked being one of them.

After a few years in forensics, Tarbell told his wife, Sabrina, he wanted to officially join the Bureau. Sabrina, eight months pregnant, approved, even though it meant uprooting their lives. After Quantico, Tarbell was assigned to the New York office, home to the FBI’s nascent cybercrime division. By this time he was 31, a little old to be the new guy.

But catching the elusive Sabu made Tarbell’s name at the Bureau. Online, Sabu’s credibility among hackers was unassailable. The FBI set him up with a new laptop in their office, where he gathered evidence against his LulzSec friends. Nine months later dozens of arrests were made, severely disabling two of the world’s biggest hacker groups.

After LulzSec, Tarbell looked for a new big case. He took an interest in Tor, the encryption software that allowed users to visit sites such as Silk Road. Tor’s protocol is a kind of digital invisibility cloak, hiding users and the sites they visit. Tor stands for “the Onion Router” and was launched by the Navy in 2002. It has since become a tool for all manner of clandestine communications, licit and illicit, from circumventing censorship in countries like China to powering contraband sites like Silk Road. Tor’s encryption is so layered, agents thought it was unbreakable. When cybercrime investigations hit a Tor IP, they would give up. The supposed impossibility only attracted Tarbell. I’m gonna take on Tor, he thought.

Tarbell briefed his supervisor, who briefed his supervisor, and so on, until they wound up in the office of the SAC, or special agent in charge. Above the SAC is the assistant director in charge—yes, an endless source of amusement when complaining about red tape in the FBI is to talk about how the SAC is just below ADIC. It took a couple of sales pitches to soften up the SAC, but in February 2013, Tarbell opened the FBI’s first Tor case: Operation Onion Peeler.

By now Silk Road was a juicy target. Many agencies were working on it, but with no success. Homeland Security Investigations had a case open. The IRS had looked into it. There was Force’s DEA case in Baltimore. And the New York DEA, which asked Tarbell for technical advice. They were using traditional drug investigation techniques, but Tarbell knew this wasn’t an operation where you could flip people up the chain, because there was no chain. You had to go straight to the top.

Bondi

ROSS WAS PADDLING through the break, lining up for a set. The beach at Bondi, just south of Sydney, sloped down to a gorgeous waterline. For Ross, the waves were among the many advantages of leaving Austin in late 2011 to spend some time in Australia with his older sister, Cally. He quickly made friends there, a lively group that went out drinking, invited him to warehouse parties, and met up to go surfing.

Ross had worked that morning but was in the water by afternoon. It was nice, the portable life. And it was made possible by his flourishing online drug bazaar. Silk Road’s usage had exploded in June of that year, after a story on Gawker brought the site mainstream attention. After that, traffic grew so fast that Ross needed technical support to maintain the site, deal with transactions, and add features like automatic payments and a better feedback system.

He’d been doing it all himself, learning on the fly, programming automated transactions and using CodeIgniter to write and rewrite the site after a benevolent hacker alerted him to some major flaws. (“This is amateur shit,” the hacker had said.) His homespun efforts worked (miraculously), but Ross lost sleep over it. To outsiders he seemed his normal genial self, but in his digital domain he was frazzled, trying to keep Silk Road running. All the while he recorded in his journal the pitfalls of running a seat-of-the-pants startup:

And yeah, that was yet another learning curve, configuring and running a LAMP server, oh joy! … But I was loving it. Sure it was a little crude, but it worked! Rewriting the site was the most stressful couple of months I’ve ever experienced.

Early on, Ross had turned to Richard Bates, a college friend who was now a software engineer in Austin. Bates helped Ross with basic programming and tended to crises like the site’s first major outage. When Silk Road took off, Ross tried to hire Bates, but Bates already had a programming job. “Have you ever thought about doing something legitimate,” Bates asked Ross, “something legal?”

By the time he got to Australia, he had banked $100,000 and was earning $25,000 a month in commissions. “It was time to bring in some hired guns,” he wrote, “to … take the site to the next level.”

Part of the problem was that Ross was grappling with what hackers call operational security, or opsec. To completely seal his two identities from one another, Ross realized, would require a kind of ruthless and elaborate secrecy. He appealed to Bates to stay quiet. Later, Ross told his friend that he’d sold Silk Road to a mysterious buyer.

He also struggled with learning how to lie. Just before New Year’s he went on a date with a woman named Jessica; he told her, like everyone else, that he was working on a bitcoin exchange. This alone constituted a security leak. I’m so stupid, he thought. But Ross got “deep” with Jessica and felt an urge to reveal himself. He lamented this feeling, the divide between intimacy and deceit. The Eagle Scout in him agonized over telling half-truths. Sitting across from Jessica, he wished he could be honest; he also wished he’d started with a better lie. But Ross did divulge the most important truth. He told her: “I have secrets.”

Ross wasn’t really interested. Driven by the failure of his previous businesses, he was determined to make Silk Road succeed. He disappeared into his work and started professionalizing his organization. He and Julia broke up again that summer. With Silk Road in his computer, there was little to keep Ross in Austin.

Sysadmin

WHEN SILK ROAD started, its leader was something of a cipher. Users and vendors only knew that there was a system administrator who’d established the site’s conceptual framework as both a drug marketplace and libertarian experiment. ¶ There was a basic ethics for that experiment. Some of Silk Road’s users were purists who advocated for full transactional autonomy—if heroin, why not howitzers and human hearts?—but the administrator pronounced “a strict code of conduct.” No child porn, stolen goods, or fake degrees. He summed it up like so: “Our basic rules are to treat others as you would wish to be treated and don’t do anything to hurt or scam someone else.”

As time went on, the administrator became an important voice, the site’s theorist and advocate for individual liberty. But ideas need a true leader. This role, Ross decided, was too important to go unnamed. “Who is Silk Road?” posted the administrator in February 2012 to the community. “I am Silk Road, the market, the person, the enterprise, everything … I need a name.”

“Drum roll please … ,” came the dramatic announcement. “My new name is Dread Pirate Roberts.”

Everyone loves The Princess Bride, and the reference was clear immediately. (Force and Tarbell, who had both seen the movie many times, got the implication as well: plausible deniability.) The mask, worn by successive generations of pirates, obfuscates the relationship between the name and the man. The christening of DPR was emblematic of Silk Road’s secrecy. It also ignited a true cult of personality. DPR was thoughtful and at times eloquent. For believers, Silk Road was more than a black market; it was a sanctuary. For DPR, the site was a political polemic in practice. “Stop funding the state with your tax dollars,” DPR wrote, “and direct your productive energies into the black market.” DPR got more grandiose over time, writing that every transaction on Silk Road was a step toward universal freedom.

In a way, Silk Road was the logical extension of the libertarian view that animates much of the Internet (not to mention the rising political tide in Washington). It was Silicon Valley in extremis, a disruptive technology wrapped in political rhetoric. DPR was its philosopher-king, envisioning a post-state digital economy, with Silk Road as the first step toward a libertarian paradise. Not only was Silk Road a slap in the face to law enforcement, it was a direct challenge, as DPR wrote, to the very structure of power.

All the more reason, of course, why the government wanted to shut it down. Ross had been flattered by the sudden media attention in June 2011, but when US senator Charles Schumer called a press conference to denounce Silk Road, he was alarmed. “The US govt, my main enemy,” he wrote, “was aware of me and … calling for my destruction.”

Nob

April 2012

nob business proposal

Mr. Silk Road,

I am a great admirer of your work. Brilliant, utterly brilliant! I will keep this short and to the point. I want to buy the site. I’ve been in the business for over 20 years. SILK ROAD is the future of trafficking.

Sincerely,

E

FORCE WROTE THIS message from one of two government laptops he was issued for his undercover mission on Silk Road. They were Dells, silver and clunky with shitty batteries, so the DEA agent had to keep them plugged in, usually in the seclusion of the guest room of his house in the Baltimore suburbs. That was also the favorite room of Pablo, Force’s cat, who would sit on the bed watching him, in his chair and ottoman, as he took to the keys posing as a high-rolling international drug smuggler.

He had constructed an elaborate identity: Eladio Guzman, a cartel operative based in the Dominican Republic whose bread and butter was moving midsize shipments of heroin and cocaine. For Guzman’s Silk Road screen name, Force chose Nob, after the biblical city where David obtains the sword of Goliath. Oh, and the Guzman character was blind in one eye. So Force put on a hoodie and an eye patch and had his 10-year-old daughter take his profile picture. In the photo, Force, aka Guzman, aka Nob, held up a sign: all hail nob.

Force knew how to put together a backstory from his years in undercover. As a young agent, he’d been on the front lines of the drug war. He grew out his hair, put bronze hoops in his ear, and inked a huge tribal piece on his back. He said he worked in construction while looking for leads in down-and-out bars, like the Purple Pig Pub in Alamosa, Colorado, the “gateway to the great sand dunes”—and also the gateway to the Rocky Mountain route for Mexican meth.

Putting himself in the mindset of a smuggler, Force saw Silk Road’s strength as communications and distribution. Hence his big opening gambit: For Guzman, Silk Road offered the opportunity for covert vertical integration from wholesale to retail. Force hoped he’d get a quick response, and he did. The day after Nob’s proposal, Dread Pirate Roberts wrote, “I’m open to the idea. What did you have in mind?”

The Pit

TARBELL WAS AT work, on the 23rd floor of the New York FBI office, early as usual. He was the kind of guy who wanted to be first in the office. Always had been, ever since college, when he started organizing his whole life on spreadsheets. Tarbell and Sabrina’s first date is still on an Excel worksheet somewhere, as is everything that’s happened since: calendar, bills, weight goals, daily run. Tarbell’s father-in-law, a longtime marine, thought Tarbell was the most regimented person he’d ever met. Tarbell set his alarm for 4:30 am, hit the gym by 5, and was showered and seated at his desk by 7 am sharp.

Tarbell and his fellow cybercops occupied a couple of dozen spots toward the back of the bullpen, fanned out around a core group of desks called the Pit. This was prime real estate, where the cool kids among the FBI’s computer clique sat. When Tarbell started he was sitting two desks and an aisle away, way over by the windows. But during the LulzSec investigation, a coveted desk opened up and he leapfrogged right into the center of the Pit.

Tarbell liked his new colleagues, especially Ilwhan Yum. As a kid, Yum moved from Korea to Long Island, where he got into videogames and later learned about networking and packets from playing competitively in college. Yum would become vital to the Silk Road case because he was the squad’s bitcoin specialist. He’d gone to the first bitcoin conference, in August 2011 in New York. From a law enforcement perspective, bitcoin screamed money laundering. But technologically, Yum thought the protocol “was, simply, beautiful.”

Across from Yum was Tom Kiernan. He’d been in the Pit the longest, 17 years, nearly since the DOS era, when he started at the Bureau as a civilian tech support guy, responding when agents’ printers stopped working. Kiernan just understood machines, backward and forward, and became the spine of the cybersquad. He’d seen every case and knew all, like the Pit’s very own oracle—just the guy Tarbell needed to help probe Silk Road’s defenses.
Tor was a vexing problem. Tarbell thought it had benefits, but he also believed that all technologies could have their purposes corrupted. In a criminal context, as with Silk Road, Tor made classic law enforcement—knocking on doors, interviewing witnesses, making deals—nearly useless. Sure, you might start to piece together the network or get closer to DPR, but you’d still have only usernames. This was not a people case, Tarbell thought. This was a computer case. The path to DPR was through his server.

Finding it was a fearsome technical challenge. Out of 1.5 billion computers in the world, Tarbell started to think about just one machine, day after day. It could be anywhere. He was looking for a nanowire in a haystack.

Founder’s Dilemma

BACK IN BALTIMORE, Force was fluffing pillows. This was his habit in the evening, a way to clear his mind before getting on Silk Road as Nob. For the first couple of weeks, Nob pushed his big Silk Road investment scheme. But DPR declined, saying essentially: This operation is bigger than you think. ¶ And it was, because Silk Road worked extremely well. DPR’s robust stewardship was paying off. To protect against scammers he created a Silk Road escrow, where all transactions would be held until settled. DPR wanted to create what he called a “center of trust,” and it was this centralized payment structure that enabled Silk Road to really take off.

So when Nob offered to buy the operation, DPR countered with quite a price: $1 billion. Nob scoffed. But in fact, DPR’s number might have been low; the scale of Silk Road commissions over the next year would in fact qualify DPR as one of the biggest entrepreneurs of the second Internet boom. Besides, he told Nob, “this is more than a business to me. It’s a revolution and is becoming my life’s work.” In essence, DPR faced a classic founder’s dilemma. “It would not be easy to pass the baton without hurting the enterprise,” he messaged Nob. “And right now that is more important to me than the money.”

DPR had never heard of the Smiths. But otherwise, Force’s mysterious new pen pal was appropriately cagey. He didn’t want to meet up for tacos. For some reason, Force always imagined DPR as a skinny white kid, probably on the West Coast based on his active hours. Force liked him, this kid he had in mind as DPR. He enjoyed getting deep into the culture of Silk Road. It reminded him of his undercover days. He thought about DPR, living a double life, and the allure—and danger—of taking on a new identity.

Force had seen it firsthand in his years in undercover. He came to love being that criminal operator big shot. But a new self comes with a price. The more Force pretended and partied, the easier it was to inhabit the part. At home he was the clean-cut, churchgoing dad. But when he was at some nightclub hunting for drug deals, liquor flowing, surrounded by girls, it was hard to believe just how comfortable he felt.

Eventually Force stopped drinking and recommitted himself to church. He’d been a hot undercover agent, but he left behind the double life that nearly destroyed him. That’s how he wound up in the Baltimore office, living in a suburban two-story with a big, solid oak tree in the backyard. But now here he was, within sight of that oak, his family in the next room, venturing again into the drug world as someone else.

Force recognized it was all a dangerous game. He knew how you could change. He could see it in DPR already. The thing about taking on a new identity is that it is fundamentally a lie. To the world at first. And then to yourself.

Force kept communication with DPR alive by talking about creating a parallel site for cartels, a pro version called Masters of Silk Road. He spent many nights in his guest room, Pablo purring by his side, forging a camaraderie with DPR through the intimacy of late-night TorChat. At times they sounded like college kids getting to know each other in the freshman dorm. “The food pyramid is bullshit,” DPR said, encouraging Nob to go paleo. Nob advised DPR against seeing the latest Batman, invited him to LA for tacos, and talked about how much Latinos like the Smiths.

StoryCorps

THE WORLD IS in flux,” Ross tells the camera. He sits across from his friend René Pinnell, recording for StoryCorps, a nonprofit that invites anyone to share their life experiences. Ross and René thought the world should know more about them, so they entered the StoryCorps booth, closed the door, and spent half an hour with each other and the camera.

In this recording, Ross is contemplative. He lives in San Francisco now. It has been a revelation. He is awed by the beauty and the entrepreneurial energy. He came at the invitation of René, whom he’d known since seventh grade. René had been an aspiring filmmaker who instead wound up in technology in San Francisco, and one day he phoned Ross, intoning the great American clarion call of opportunity out West. Two weeks later, Ross showed up on his friend’s doorstep.

In the video, they get nostalgic about childhood. There was the time the two of them tried to steal extra Tater Tots in the lunch room at West Ridge Middle School. The way Ross would eat his peanut butter chocolate wafers, precisely, by nibbling down the layers. How uncool it was when Ross had a sleepover and some bad kids stole a year’s worth of change he’d saved.

Of course, they talk about love, as young men do. Ross reminisces about Ashley, his first, and her great tits. The first time they’d hung out, they did psychedelics, something called AMT. They got it from his neighbor Brandon, a “super-brilliant physics student who was into all of these research chemicals.” Ross was still a teenager then, lying on the floor, expanding his mind next to a beautiful girl for eight hours.

Life is a fluctuating value, René says, like currency. René thinks his friend is a trader. René talks about how Austin is “the meh of startups,” whereas San Francisco is “the Mecca.” It’s late 2012, a time of fever dreams in the Bay Area, full of people wanting to “change the world” and make a lot of money in the process. René may not know it, but he is sitting next to someone doing just that.

Ross and René wonder: What will happen in 200 years? “I want to have a substantial positive impact on the future of humanity by the time I die,” Ross says. René asks Ross if he thinks he’ll live forever. Ross looks up, breaks into a tiny smile. “Yes,” he says. “I think I might.”

Hugs

AS SILK ROAD became a true global market, DPR reveled in his role as leader and libertarian evangelist. He created a book club, where users could polish their dogma from the sacred texts of von Mises himself. He talked more about a near future when our current governments would seem like ancient history, along with “the pharaohs” and their “armies of slaves.” He extolled the Silk Road faithful for being on the front lines of revolution. “Thank you,” DPR said, “for your trust, faith, camaraderie and love.” He offered them “hugs not drugs,” then amended it: “wait, hugs AND drugs!”

The community responded in kind, likening DPR to Che Guevara, calling him a “job creator” and declaring that his name would live on “among the greatest men and women in history.” Silk Road had become a brand cult, with tens of thousands of fanatical users. And DPR was their very own Steve Jobs. Force sensed DPR’s swelling confidence. He’d been talking to him for a year, taking in DPR’s personality and passion. Force could appreciate the appeal. It must be intoxicating, bringing an idea to life, projecting your will into the world through encrypted code and transactions. Sometimes DPR said that he sensed the scale of this achievement and would hear the theme to Tron playing in his head. This was the new spirit of DPR: a self-created beacon in the darkness, spreading the good word through libertarian jubilee, holding aloft his lantern of truth. It was a lonely outpost, however. DPR said so to Nob. He called himself a person “who hides behind computers.” At times DPR wished they could meet. Instead they shared a mix of truth and fiction about their lives.

NOB: you doing good?

DREAD: yes sir, today is a good day.

NOB: so that black cloud that was over your head has gone?

DREAD: the new look rolled out with minimal issues, woke up next to a beautiful woman, and I’m listening to one of my favorite bands/songs … and eating fresh strawberries.

They talked shop: site fixes, the odd “holiday slump” in drug sales, the human resources problems of a clandestine telecommuting workplace. This was a big problem. To grow, DPR said, he had to build a strong workforce. A leader needs support so he can focus on the future.

Health and Wellness

I JUST WANT to let you know that your work hasn’t gone unnoticed,” DPR wrote to Chronicpain, aka Curtis Green, the Mormon grandpa in Spanish Fork, Utah. “I’d like to offer you a position.”

Green had been on Silk Road for some time, and he’d chosen that screen name because of his own chronic pain, caused by a back injury he’d sustained while working as an EMT. On disability, Green had become an amateur pharmacologist, learning the ins and outs of opiates. Green had always been the hobbyist type, ever since his high school obsession with ham radios, which he used to talk to strangers all over the world, including astronauts on the International Space Station. Silk Road fulfilled his yearning for community and technical intricacy, combining computers with his interest in “safe drug use.” With DPR’s approval, Green started Silk Road’s Health and Wellness forum, where he advised people on how to snort ephedrine, cautioned against Fentanyl for the uninitiated, and explained to someone that it’s not a good idea to inject peanut butter or shoot heroin into your eyeball.

When Green’s diligent forum-moderating turned into a job offer from DPR, he was thrilled. DPR sent a job description, which included customer service and resetting passwords. Green (taking on a new admin handle, Flush) worked 80 hours a week, mediating drug sale disputes from his lounger, Fox News running in the background.

DPR was a complicated boss. He could be a hard taskmaster, haranguing Green for being even one minute late to an appointed time on TorChat. Green was chagrined when he got no Christmas greeting. But other times DPR was full of generosity, staking Green in a poker tournament (and being unfazed when Green lost it all). Like a digital-era don, he could be affectionate and magnanimous in public but decidedly less humane behind the scenes. He gave audience to loyal users seeking favors—one guy got help buying a wedding ring—but was decidedly unsympathetic to the real consequences of his business.

Green forwarded one troubling customer service complaint from a woman whose brother overdosed on heroin from Silk Road and noted that under the current system, children could use the site. Perhaps that was a hair too much freedom, Green said. DPR erupted: “THAT’S MY WHOLE IDEA!” Any constraints would destroy the fundamental concept, he said, and refused any assistance for the grieving sister. And yet Green stayed on, despite the insensitivity and ethical contradictions, becoming one of Silk Road’s most trusted employees.

On Silk Road, however, trust only went so far. DPR demanded a scan of Green’s driver’s license. It was a loyalty test. Green obliged, even though it exposed him while allowing DPR to remain in the shadows. Like Force, Green felt like he’d established quite a bond with DPR—partners in a secret world. But not all secrets are partnerships. No matter how close Green or Force or anyone else got to DPR, no one had any idea who he was.

Fences

TARBELL HAD THREE computers on his desk, as did Kiernan and Yum. The cybersquad crew looked for any flicker of information that would crack open the dark web. But their investigation was moving slowly. They explored the site, read the forums, and crawled Reddit, looking for Silk Road community members talking to each other or to DPR about cryptographic weaknesses they’d discovered. But a month went by with no traction.

The crew ate lunch together every day at 11:30 on the nose like the habit-happy cops they were. Most of the time they picked up sandwiches downstairs at the deli, where the guy behind the counter knew them all by their order. Kiernan would be happy with chicken cordon bleu forever, and Tarbell was such a fan of the chicken parmesan that when he’d occasionally get a salad the deli guy would say, “Awww, what’s the matter, Mr. CIA? No chicken parm today?”

Tarbell called Yum his “work wife.” They were a good team, he thought: the thinker and the talker. Tarbell was the talker; he had by now emerged as the dominant personality in the Pit. The dues-paying rookie of the previous year had given way to a raucous, confident alpha type who bristled when he heard rumblings from Washington about ownership of the Silk Road investigation.

The case had become an enormous bureaucratic battle, as every agency tried to plant its flag. The Baltimore task force—where Force’s case operated—was the most aggressive, claiming complete ownership and bad-mouthing the FBI cybersquad in particular. “They think we’re a joke, poking around on the Internet,” Tarbell told Yum. “But we’re going to prove them wrong.” The other agencies, he noted, had been at it for a while, “and they don’t have fuck-all.”

But in the bureaucratic muddle that is the United States government, there is no clear jurisdiction for cybercrime. It’s a growing field that’s fueling law enforcement funding, which attracts egos and politics. Silk Road represented the new frontier of crime, a digital-era Wild West. As with the original frontier, Washington wanted to fence it in—and whoever brought law to the lawless would be a hero. Subdue the digital frontier and there was a star waiting for you, which was why the Silk Road case had become the largest online manhunt in history.

Call Me

GREEN WOULDN’T STOP talking, even covered in cocaine. That was how Force found him when the SWAT team finished ransacking his house. Force was running that show; as Nob, he’d orchestrated the shipment of coke, and the whole raid was part of the growing Marco Polo task force investigating Silk Road. He’d watched Green take the bait from a command post across the street, and when he walked in a few minutes later, Green was cuffed on the floor, blabbing already. Green had more answers than Force had questions. He talked and talked and talked until Force couldn’t stand it. Said he was a former EMT; he was just trying to help people; they could have just knocked; he thought the package was something else, a totally legal drug called N-Bombe.

Shut the fuck up already, Force thought.

Nevertheless, Green was a tangible lead in the Silk Road case, a corporeal asset rather than just letters on a screen. As Green was led to the squad car to be booked on possession by the local cops, Force put his number in Green’s phone and said, “When you get out, call me.”

In jail, Green jawboned for hours to anyone who would listen, even declaring that he had been asked to cooperate with the DEA, at which point his tattooed cell mates told him to stop talking. When Green was released on bail, he went home and found his door still broken. His daughter had cleaned up some. In his bedroom the cops had apparently discovered that this particular Mormon grandpa owned a dildo, which they left for him standing straight up on the bed.

Home alone with his two Chihuahuas, Green cried like a baby. “I’m a good little Mormon boy,” he said to himself. His thoughts grew dark. He loaded his dad’s .32. Then he looked down the barrel and threw it across the room. Green would be the first to admit that he was too chickenshit for suicide. He ran into the living room and threw himself onto the couch, where his Chihuahuas joined him, licking his face while he fell to his knees to pray. Eventually Green decided to get up, get his phone, and call DEA special agent Carl Force.

 

Driverslicense-1.pdf

IT WASN’T UNTIL Force spent some time on Green’s computer and saw DPR’s messages—“Why aren’t you clearing out your accounts?” “Get back to me ASAP”—that he realized they’d caught a big fish in their net. This guy was a DPR lieutenant. Force mobilized quickly, working with the task force to put Green up in a Salt Lake City Marriott and debrief him.

But DPR was jittery, and he’d noticed that his trusted admin had been offline for a few days. A Google search revealed that Green had been arrested, and DPR suspected he would flip. Moreover, he got a message from another employee, Inigo, that $350,000 in bitcoins had just disappeared from various accounts. Inigo quickly traced the theft to Green’s admin identity. DPR went into crisis mode, communicating with his confidants, scrambling for a solution. “This will be the first time I have had to call on my muscle,” he told Inigo. “Fucking sucks.”

Moments later, DPR messaged Nob that he had a “problem” in Utah that required violence. According to the backstory Force had created for Nob, his criminal repertoire included enforcement and collection talents, so he acted the part. Sitting in the Marriott, Force received a PDF of the target, opened it, and discovered a scan of Green’s driver’s license photo. Then he looked across the table, where at that very moment Green was half-asleep. Well, this sure is an opportunity! Force thought.

NOB: do you want him beat up. shot, just paid a visit?

DREAD: I’d like him beat up, then forced to send the bitcoins he stole back.

DREAD: not sure how these things usually go.

Green claimed he hadn’t stolen any bitcoins and protested that the task force had had his computer when the money went missing. But Force didn’t want to talk about the money. He used DPR’s request to construct an elaborate plan.

DREAD: how quickly do you think you can get someone over there? and what does that cost you?

Force got Green to sign a waiver, thereby commencing his role in an impromptu staged torture sting against DPR. Soon Green was being dunked in the bathtub of a Marriott suite by phony thugs who were in fact a Secret Service agent and a Baltimore postal inspector. Force recorded the action on a camera. “Did you get it?” Green asked, wet and wheezing on the floor. He’d felt like their simulation was a little too accurate. They dunked him four more times to get a convincing shot.

While waiting for news from Nob, DPR considered his options. A Silk Road user named Cimon, a trusted adviser who had guided DPR on opsec, programming, and leadership, asked DPR when a transgression against Silk Road requires a lethal response. “If this was the wild west,” DPR said, “and it kinda is, you’d get hung just for stealing a horse.” A few minutes later, Inigo chimed in, “I don’t condone murder but that’s almost worthy of assassinating him over lol.”

Later that day, DPR messaged Nob.

DREAD: ok, so can you change the order to execute rather than torture?

DREAD: he was on the inside for a while, and now that he’s been arrested, I’m afraid he’ll give up info.

Of course, DPR was right that Green had been flipped—by the very same man he’d just hired as an assassin. It was a surprising escalation. The Silk Road leader, who waxed lyrical about “respecting” the Silk Road community, was now pondering pricing for murder.

DREAD: never killed a man or had one killed before, but it is the right move in this case.

DREAD: how much will it cost?

DREAD: ballpark?

DREAD: less than $100k?

DREAD: have you killed or had someone killed before?

It was like Scarface on fast-forward, Force thought. But he played right along. Over a week or so, Force conspired with his team to complete the fake death of Green. Force sent DPR photos of the staged torture, followed by photos of Green, facedown on the floor, pallid, smeared with Campbell’s Chicken & Stars soup—the supposed aftermath of asphyxiation. Green holed up in his house (he had to stay out of sight as part of the ruse) in a kind of self-imposed witness protection, and Force went back to Baltimore. DPR sent $40,000 to a Capital One account controlled by the government as an advance. DPR never got back the stolen bitcoins, but once in receipt of the putative proof of death, he sent another $40,000 for a job well done.

NOB: you ok?

DREAD: I am pissed I had to kill him.

DREAD: but what’s done is done.

DPR had momentarily wrestled with his decision. He had talked to Inigo about how he just wishes the best for people, and loves them in the libertarian spirit—even Green, in flagrante delicto—but ultimately concluded that his AWOL employee had become too much of a liability. And so, DPR’s principled, technological stand against the war on drugs slid into murder. Like so many revolutionaries before him, the idealist became an ideologue, willing to kill for his beloved vision. At one point, DPR corrected Inigo that this action was not revenge; it was justice—a new justice, according to the law of the Silk Road.

Back in Baltimore, sitting in his guest room with Pablo, Force thought about DPR’s shift. He wondered: What changed? DPR was asking himself the same question. Moral choices blur when your identity is shifting. This was the irony behind the very idea of the Dread Pirate Roberts moniker—an inherent danger that the wearer would become the mask. Unmoored, DPR sensed that he was in a state of becoming:

NOB: what have you learned?

DREAD: well, I’m also learning who I am. I don’t think this will be the hardest thing I’ll have to do.

NOB: what could be harder?

DREAD: I don’t know.

DREAD: maybe I’ll be faced with a decision where lives of innocent people will depend on the outcome.

As if seeking a makeshift moral compass among murderers, DPR asked Nob to let him know if he was abusing his authority. “That is what friends are for!” Nob replied. DPR confided to Inigo that one of his deepest fears was “being wildly successful” and “being corrupted by that power.” Nob also warned his online comrade about that power, how it could consume you. In his office, Force himself had put up a picture of Jesús Malverde, the Mexican narco-saint, as inspiration for Nob, and felt the pull of the folk hero bandit. He reminded DPR not to “lose yourself.”

How could he not? Now astride a multimillion-dollar drug operation that he’d built in less than two years, Ross was no longer the tenderhearted soul who agonized over telling one lie to a young woman over a glass of wine. His diary had changed from a story about doubts and hopes to a catalog of hard-nosed empire-building.

The triumph of Silk Road confirmed its creator’s belief in his own myth. “What we are doing,” DPR wrote to his followers, “will have rippling effects for generations to come.” In June 2013 the site reached nearly 1 million registered accounts. And the Feds were nowhere in sight.

Until one afternoon just around that same time, back in the New York FBI cybercrime office, when Tarbell and Kiernan leaned forward and finally saw something interesting on one of their screens. They’d been at it for weeks, farting into the same chair cushions in the Pit, running the Tor bundle on one monitor, staring at lists of numbers on another, when one of those numbers surprised them: 62.75.246.20. They looked at each other in disbelief—and then back at the terminal, which was displaying the true IP address of the Silk Road server.

END OF PART 1

This article includes reporting by Nick Bilton, whose book on the Silk Road case will appear in 2016. This story appeared in the May 2015 issue of WIRED.

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silk_road_mobile_pt2

Thor

“I imagine that someday I may have a story written about my life and it would be good to have a detailed account of it.” —home/frosty/documents/ journal/2012/q1/january/week1

THE DESCENT WAS stunning. Chris Tarbell, a special agent from the New York FBI office, was in a window seat, watching a green anomaly in a sea of blue as it resolved into Iceland’s severe, beautiful landscape. On approach to Keflavík International Airport, he could now see the city of Reykjavik coming into view. And just beyond that, perched on the edge of a moss-covered lava field: the massive matte-white box that housed the Thor Data Center. That’s why Tarbell and two US attorneys had come all this way. Thor was the home of a computer with a very important IP address, one that Tarbell and his FBI colleagues had discovered back in New York—the hidden server for a vast online criminal enterprise called Silk Road.

They’d been working on this case for months, as had federal agents across the country, in a wide-ranging digital manhunt for Dread Pirate Roberts: the mysterious proprietor of Silk Road, a clandestine online marketplace that functioned like an anonymous Amazon for criminal goods and services. Silk Road investigations had been launched by Homeland Security, the Secret Service, and the DEA office in Baltimore, where an agent named Carl Force had been working an undercover identity as a Silk Road smuggler for more than a year.

Tarbell and his team—known as Cyber Squad 2 (or CY2 for short and “the Deuce” for fun)—were relative newcomers to the case. The other agencies had dismissed the FBI, partly because of interagency bluster and partly because the traditional agents who thought casework was all guns and grime and grit had no respect for the eggheads from cybercrime. But in the midst of this enormous law enforcement effort—mostly fruitless so far—Tarbell and CY2 had found the first promising lead in the case.

Cybercrime agents spend a lot of time at their desks, and it was exciting to be in the field. Down below they could see Iceland’s fierce geology, all jutting rock built up from the water by volcanoes. Beneath the surrounding ocean are the massive cables that make the country an important location for web traffic; the island is nearly equidistant between North American and Europe, and its forbidding geography and climate reduce cooling costs and provide free geothermal power. One of the attorneys told Tarbell about Iceland’s tectonic forces—the North American and Eurasian plates, slowly tearing open a growing chasm. Really puts you in your place, Tarbell thought.

His investigation had started entirely at his desk with virtual gumshoe diligence, poking around Tor’s IP publishing protocol and spending time on Silk Road looking for chatter about the site’s security. His lucky break came from a thread on Reddit: A user posted a warning that Silk Road’s IP address was “leaking”—visible to other computers. Dread Pirate Roberts (or DPR, as he was often called) had been alerted to the problem by a user but ignored the warning. Silk Road’s success was making DPR arrogant. He had let down his guard, confidently telling colleagues that the site would never be found.

Tarbell threw data at Silk Road, hoping to see the leak. He entered usernames with bad passwords (and vice versa) and pasted data into input fields—all the while using regular old freeware to analyze network traffic and collect the IPs communicating with his machine. Then he tested those. On June 5, 2013, after staring at IP addresses for hours, Tarbell pasted one of them—193.107.86.49—into a browser and suddenly there it was: the Silk Road Captcha field. He showed it to fellow agent Ilhwan Yum and to Tom Kiernan, the civilian computer technician who formed the technical backbone of the cybersquad. This was what the team had been waiting for: a misconfiguration somewhere on the site that revealed the real IP address of Silk Road, which Tarbell proceeded to trace all the way to the state-of-the-art facility in Iceland.

Tarbell had been to the island nation once before and knew some of the officials at the meeting. There was an Icelandic prosecutor present—Tarbell was mildly distracted by how attractive she was, with her fitted skirt, secretary glasses, and hair in a bun—and an attaché from the US embassy. It’s a delicate thing, making requests of another government—a US attorney had written up an official letters rogatory petition, requesting that Iceland honor the bureau’s investigative requests—but the Icelandic authorities were accommodating, and the meeting was over in an hour. Not long thereafter, an Icelandic police detachment entered the immaculate foyer of the Thor Data Center.

 

Once on the ground in Reykjavik, Tarbell and the lawyers met with their counterparts and explained why they’d come. Silk Road had eluded law enforcement for almost three years because it ran on Tor, a kind of cryptographic camouflage that made it nearly impossible to see the site’s users, vendors, or servers. Until Tarbell made a chance discovery.

What kind of data center has a foyer? The kind that also has a gleaming glass front and a spotless floor and houses the world’s first zero-emission supercomputer. Cybercrime forensics often means untangling wires from machines stuck in some basement. Thor looked like the future. Past the foyer’s key card entry was a former airplane hangar in which sat a double-high shipping container, bright blue with silver ducts, full of servers. Inside were three rows of blades lined up floor to ceiling, flashing with blue lights. There was a chill in the air and the thrum of a thousand fans, all powered by Vulcan forces from the rock below. The Icelandic authorities found the correct box and discovered that it had a mirror drive, a duplicate set of contents. They pulled the mirror, returned to Reykjavik, and handed the drive to Tarbell. And just like that, he was holding Silk Road in his hand.

Even on first glance the site’s volume was surprising: On July 21, 2013, around the time Tarbell landed in Iceland, DPR’s account received 3,237 transfers totaling $19,459, which would give DPR an annualized income of more than $7 million. The data center also kept system logs for six months; they could see all the other computers that had recently communicated with this machine. It was an investigative windfall.

After returning to New York, Tarbell started unspooling the electronic threads that led from the Iceland machine to computers around the world. They looked at traffic recorded for port 22—the encrypted connection where admins log in—and discovered several non-Tor IPs: a backup near Philadelphia, a hosting proxy server in France, a VPN in Romania.

On the wall of the CY2 computer lab, Tarbell mounted an 8-foot sheet of plotter paper and constructed the classic crime investigation visual, with a skein of lines mapping the complicated relationship of leads and evidence. But rather than the traditional godfather surrounded by his capos, this chart centered around a server in Iceland and a sprawling cryptographic computer network.

Tarbell was a visual thinker; he liked to see the connections. One of those connections was to an IP address that was the last known login to the Silk Road VPN. Next to it Tarbell drew a question mark. A subpoena revealed the IP’s physical location: Café Luna, Sacramento Street, San Francisco.

Joshua Terrey

WHEN HOMELAND SECURITY agents showed up at Ross Ulbricht’s front door in San Francisco, his new roommates were surprised. They thought the quiet guy from Texas who’d just rented their extra room for a thousand bucks was named Joshua Terrey. The agents must have found that interesting, since Joshua Terrey wasn’t one of the nine names they’d found in a stash of fake IDs at the Canadian border customs office, all directed to this address and featuring Ross Ulbricht’s picture.

Ross had moved into this house after leaving Austin, where he’d grown up as a smart kid from a suburban family with an adventurous streak. Ross was handsome, charming, and always an overachiever, studying physics and engineering on scholarships. But he’d abandoned lab work to pursue an idea that brought together his technical smarts, entrepreneurial spirit, and newfound libertarian social philosophy: Silk Road. He’d come west, to the Mecca of startups, where he managed his powerful operation in secret.

Even though Ross had only recently moved into this sublet in West Portal, a neighborhood of single-family homes and strollers, he’d scored the master bedroom. His roommates thought that the guy named Josh, who had answered their Craigslist ad, was a currency trader. They did think it was weird that he had no cell phone, paid in cash, and was always on his computer. Neither friends nor family had any idea that Ross had a secret alter ego: Online he was Dread Pirate Roberts. Nor did they suspect that the young man who ran what began as a politically motivated black market had become the leader of a criminal organization, a ruthless operator who had decided to kill one of his employees as retribution for theft (and as a sacrifice necessary to protect his political objectives).

If Ross was nervous about being discovered when the Homeland Security agents interviewed him, he didn’t show it. He did not tell them he’d bought the colorful array of fake IDs so that he could covertly rent additional servers to deal with Silk Road’s exploding scale and security challenges. The IDs were high-quality counterfeits, holographic features and all. But now they were in the hands of the Homeland Security agents at the front door. Ross was polite but knew he could refuse any questions.

Ross was spooked by the visit. He moved again a short time later to another sublet, in the city’s Glen Park neighborhood, but decided to use his real name. One of his new roommates, Alex, liked Ross right away because he was charismatic and easy to talk to.

And, Alex observed, Ross’ focus was impressive. He wasn’t the type of guy to procrastinate watching cat videos on his Samsung 700z. He didn’t smoke or drink much, although he sometimes played his djembe, a west African drum and one of his few possessions. He never brought friends over and seemed not to have asingle memento. Nor did Ross get mail. “Sometimes,” one roommate said to Alex, “I feel like Ross is hiding from someone.”

Still, they couldn’t have guessed that Ross, the new guy in their cheap share who liked giving hugs and hanging out shirtless, was sitting on their garage-sale furniture with that Samsung on his lap presiding over a criminal empire.

 

Before the agents left, Ross did volunteer that “hypothetically” anyone could have shipped drugs or fake IDs to him via a website called Silk Road. A strange thing to mention—and duly noted by the agents—but they weren’t there to talk about Silk Road, whatever that was. The agents left and took the fake IDs with them.

 Uneasy Lies the Head

“MONEY IS POWERFUL,” DPR wrote to the Silk Road faithful, “and it’s going to take power to effect the changes I want to see.” By that time, DPR was a millionaire many times over, but those resources, he told his followers, were for the revolution. Freedom, after all, needs financing.

DPR had founded Silk Road as a digital instantiation of the libertarian ideal: a frictionless marketplace where everyone had freedom as long as it didn’t impinge on someone else’s freedom. For DPR and the community that grew around him, Silk Road was about more than contraband; it was a movement. As Silk Road quickly grew, DPR’s pronouncements became more grandiose. He wrote that “every single transaction is a victory” in weakening the “thieving, murderous” state. What began as a belief in free choice came to sound like revolutionary dogma.

It made for ambitious business plans. DPR wanted to expand his liberty-fueled brand into an empire, with his own Silk Road–affiliated bitcoin exchange, credit union, and encrypted communication service. Buoyed by quick success, DPR shared the heady enthusiasm of the licit startup world. Whereas he’d once considered selling Silk Road for $1 billion, he told a reporter in a rare, encrypted chat interview that Silk Road was worth 10 figures, maybe 11.

But behind the scenes, Ross faced constant crises. There were technical problems, management issues, a quickly changing marketplace, and the volatility of bitcoin. There were scammers on the site. And even as Silk Road made more money, the cost to maintain it rose. Ross, feeling besieged from all sides, recorded his efforts in a log.

04/03/2013

Spam scams have been gaining traction. Limited namespace and locked current accounts.

Blackmail too was a problem. Hackers had figured out how to launch denial-of- service attacks on Silk Road, and DPR was forced to pay “protection” to the tune of $50,000 a week. In May 2013, hackers shut down the site for a week, and many users wondered if it was the work of a competitor. Atlantis, a new Tor-based illicit-goods bazaar, had just launched with a slick YouTube trailer and a group chat with reporters in which a spokesperson named Heisenberg offered the serious burn that Atlantis was the “Facebook to [Silk Road’s] MySpace.”

05/02/2013

Attack continues. No word from attacker. Site is open, but occasionally tor crashes and has to be restarted.

DPR’s own staff was growing, although it was hard to find reliable subalterns. Batman73—a dealer named Peter Nash in Australia—was a cokehead. Inigo ran the site’s book club, which DPR appreciated, but was the kind of guy who lived part-time on a boat, smoked a lot of weed, and was as organized as that lifestyle might suggest. DPR liked Libertas, though, and Smed was solid, offering rapid-response technical support.

05/03/2013

Helping smed fight off attacker. Site is mostly down. I’m sick.

The burden of leadership was getting to DPR, and his fluctuating moods played into the theory that the moniker was actually operated by multiple people. DPR encouraged this perception. In an interview with Forbes, he said that he was actually the successor to Silk Road’s creator. It worked. On Silk Road it became great speculative sport to decipher the many facets of DPR, with users believing they could even detect when the different DPRs took the reins.

“You are a busy guy. Actually I think you are going to kill yourself,” said a friendly message sent to DPR by a Silk Road vendor named Nob. “Take a vacation.” DPR believed that Nob was a Puerto Rican cartel middleman named Eladio Guzman, but he was in fact DEA agent Carl Force. Force had spent more than a year developing his undercover identity on Silk Road in an effort to get close to DPR. They’d become confidants, spending nights chatting at such length that DPR trusted Nob when he needed enforcement muscle.

It was Nob whom DPR hired to kill his employee, Curtis Green. Force then coerced Green into faking his own death as a ruse. Force was surprised to see DPR’s moral collapse up close, but then again, he’d seen this kind of thing before, during his younger DEA years in undercover. He too had experienced the temptations that came with a double identity. In fact, his secret life as a hard-partying operator had nearly destroyed his regular life. He’d left all that behind and recommitted himself to Christ. The Silk Road case was his first undercover role since those days, and it was a big one. Because of his tenure online as Nob, Force was able to carry out the supposed “hit” on Green, setting DPR up for a murder conspiracy indictment while at the same time cementing their relationship. Nob and DPR had become comrades-in-arms.

Now Nob wanted to capitalize on DPR’s apparent struggle. “You need a contingency plan,” Nob wrote. Force hoped that the mounting paranoia would eventually allow him to orchestrate what DPR would believe to be an escape—right into the arms of the DEA.

DPR confided his worries about “LE,” or law enforcement, not realizing that he was talking to the DEA. That might have been a lapse in judgment in a realm that was full of speculation about narcs and informants. But DPR wanted to believe his friend Nob. Silk Road, after all, was built on DPR’s confidence system. And besides, he was lonely. “I have no one to share my thoughts with,” DPR posted to the wider Silk Road community at one point. “Security does not permit it, so thanks for listening.”

05/26/2013

Tried moving forum to multi .onion config, but leaked ip twice.

DPR had also gotten lazy with his operational security. That diary he kept was a bad idea, for starters. Growing vanity had become a weakness. DPR’s self-taught programming was catching up with him as well, leaving holes in Tor’s invisibility cloak. And yet he would tell his admins there was nothing that could get traced back to them. When one user with a technical background private-messaged DPR to warn him that he should know the precise physical location of his servers, DPR brushed it aside. The tipster warned that the servers could be copied easily. Don’t worry, DPR said. The servers are secure.

Lab1a

BACK IN NEW York, Kiernan was busy re-creating the entire Silk Road system in their lab. Once it was configured, Tarbell and his team could access the system as superusers—seeing Silk Road as DPR—and learn the site’s mechanics, communications, and structure. It was thrilling, of course, to fire it up for the first time. They wondered what they would see. Tarbell could immediately appreciate DPR’s sense of industry, how hard he worked to expand and manage the site under incredible duress. Tarbell thought: I guess he’s really earning that commission.

It was impressive. Especially because Tarbell could tell that DPR was not a professional programmer. The server was a “noisy box,” clearly the work of an autodidact, a coding palimpsest that invited eventual discovery. The pseudo code was full of comments describing various technical experiments that were often run on the live server. Kiernan and Yum found the private messages, the forums, a bitcoin escrow account (from which DPR extracted his cut every Saturday night), and the main bitcoin server showing all vendor transactions.

They spent a lot of time in the lab, which they dubbed the War Room. It felt like college finals week in there, every day. The group would churn through Silk Road material, bringing lunch in from the deli downstairs and getting loopy by the afternoon, when Tarbell would call for a seltzer break and dance around with the bottle, singing the mellow gold classic “Afternoon Delight.” Over time the jokes got weirder, like when Yum put up a sign in the War Room that said: Lab1a. To the delight of the cybersquad, no one in the computer-illiterate realm of the FBI noticed that this was also leetspeak for some sensitive lady parts.

While Yum and Kiernan worked on the machines, Tarbell combed through 1,400 pages of DPR’s chat logs so as to really understand him. DPR was different things to different people, sometimes solicitous and businesslike, other times volatile and narcissistic. Eventually, he embraced murder as a necessary business practice.

DREAD PIRATE ROBERTS 3/27/2013 23:38

In my eyes, FriendlyChemist is a liability and I wouldn’t mind if he was executed … I have the following info:

Blake Krokoff

Lives in an apartment near White Rock Beach

Age: 34

Province: British Columbia

Wife + 3 kids

Always the businessman, DPR first invited the Hells Angels to become vendors on Silk Road, suggesting that Redand­white “read the wiki and forums.” Then the two got back to the cost of murder. Hit men apparently get a commission, according to this Hells Angel, if the target owes money. And if you want it to look like an accident, rates go up. A “clean hit” would cost about $300,000 (travel expenses included). DPR had sticker shock. After all, he’d only paid $80,000 for the Curtis Green hit. They haggled.

DREAD PIRATE ROBERTS 3/31/2013 8:59

Don’t want to be a pain here, but the price seems high. Not long ago, I had a clean hit done for $80k. Are the prices you quoted the best you can do?

REDANDWHITE 3/31/2013 11:16

I’m sorry, but we can’t do anything for that price. Best I can do is 150 and even that is pushing it.

In the interest of a “business relationship to be” the Hells Angels agreed to $150,000, or 1,655 bitcoins at the time. “Good luck and be safe” was DPR’s sign-off. The next day they debriefed.

REDANDWHITE 4/1/2013 22:06

Your problem has been taken care of … Rest easy though, because he won’t be blackmailing anyone again. Ever.

DREAD PIRATE ROBERTS 4/2/2013 00:55

Excellent work.

Tarbell had never seen anything like it. Here was a date- and time-stamped record of an entire criminal conspiracy as it unfolded. Turned out, Redandwhite told DPR, the blackmailer they killed was working with another guy known on Silk Road as Tony76, an infamous scammer. DPR didn’t hesitate to add him to the invoice. But Tony76 had housemates, and they were also involved. Maybe. Probably. Fine, DPR said. Get them too, and send photographic proof when the job is done. Meanwhile, DPR and Redandwhite spent some time troubleshooting the Hells Angels’ new chat app and privacy plug-in (“Please upload some screenshots of the settings”) while also planning and pricing (“no bulk discounts”) the next set of executions.

DREAD PIRATE ROBERTS 4/8/2013 18:50

I see your problem, you need port 9150, not 9151 … hmm … $500k in btc (3,000 @ $166/btc) has been sent to:

1MwvS1idEevZ5gd428TjL3hB2kHaBH9WTL

A week later:

REDANDWHITE 4/15/2013 10:11

That problem was dealt with.

Tarbell had been reading DPR’s correspondence in reverse order, and it was a strange thing, winding DPR’s life backward, from willing executioner back into idealist concerned with individual happiness. Some libertarian utopia, Tarbell thought. Although he wasn’t exactly surprised. All systems are vulnerable to corruption. Like the Internet itself, Tarbell thought, which began as a wonderful free prairie until people took advantage of that freedom. That’s why, he thought, it needed a sheriff. Up on Tarbell’s chart was an IP address with a name next to it: Frosty. This was an ID they’d found on the Iceland box. But they didn’t know what it meant until Yum and Kiernan cross-referenced it with some other evidence they’d collected. It turned out that the Silk Road servers had a login system that created one trusted computer for all the other machines, whose encryption keys all ended with frosty@frosty.

 

Reading through DPR’s correspondence, Tarbell was surprised to find evidence of more hired assassinations, this time a response to blackmailers. It was a complicated scenario, but what Tarbell put together was that a user called FriendlyChemist was blackmailing DPR. Another user called Redandwhite, claiming to be a member of the Hells Angels, agreed to kill the blackmailer and, soon, others. For a handsome fee, of course.

This meant that these computers shared one key friend, a single machine they could all talk to. Tarbell looked at his chart, festooned with a network topology. One of those nodes must be Frosty, and whoever sat at its keyboard was Dread Pirate Roberts.

As the case accelerated, Tarbell and his team started working long hours and weekends, jackets off, sleeves rolled up, long past the late dusks of summer. Tarbell actually loved that feeling on Friday at 5 pm when the air conditioner turned off automatically, the bullpen emptied and grew quiet, and he realized he’d been yelling all day but could now finally think.

Except that it was high summer. This being a federal building, the air-conditioning was on a timer. There’d be no circulation until Monday at 8:15 am. So by midday on Saturday, when the place was boiling, Tarbell would strip down to his underwear right at his desk.

The only room with constant air-conditioning was the lab, which had to be cooled because of the electronics. So one day, Tarbell and Yum made a desperate attempt to transport some of the chill to their desks using fans. It kind of worked. And there they sat in the middle of the FBI office, Tarbell sweating in his skivvies, with a football game on in the background and a series of fans stretching back to the well-cooled room where the ersatz Silk Road server hummed along, still keeping one key secret.

Glen Park

ROSS AND ALEX had become friends at the new house. Some nights they’d watch King of the Hilltogether, which reminded Ross of home, as it was a satire of a suburban Texas family like his own. Eventually Alex met that family when they all visited for a weekend. Ross’ parents seemed like nice folks who had raised a nice son. Settling into his room, Ross bought a few things to make life more comfortable: a lamp, a white leather couch from a garage sale, a standing desk for his Samsung. Online, however, things were less settled.

Across the country, Force, the DEA agent, was hoping to capitalize on DPR’s difficulties. He told DPR about “Kevin,” a supposed source of counter-intelligence on the growing Silk Road investigation. Nob explained that like all good cartel-affiliated players, he had “a guy on the inside,” a dirty Department of Justice employee on his payroll. Kevin, of course, was Force himself, and he had a lot of valuable information for DPR. Force told his supervisors that this informant game would make Nob seem omniscient and therefore more trusted. Citing Kevin, Nob fed DPR intel and predicted busts of Silk Road users and vendors. Things were getting dicey out there, Nob said. He pressed DPR on the need for a “30 seconds flat” escape plan, suggesting various itineraries.

DREAD: Can you explain to me why you chose this route?

NOB: Algeria does not extradite to the US.

NOB: Second you don’t want to take a plane out of your mother country.

Ross had in fact taken some preparatory steps. He flew to Dominica, a tiny tax haven island in the Caribbean, and started an application for “economic citizenship.” He tried to cultivate successors in case flight became necessary. DPR had created a special forum called Staff Chat for his elite admins, including Batman73, Inigo, and a newcomer called Cirrus. DPR told his admins how the pressure was getting to him, how he wanted time away. Even amid the rising chaos swirling around Silk Road, DPR started taking days off, leaving daily operations to his lieutenants. Ross spent a weekend with his old flame Julia, a free-spirited and sensual young photographer he’d met at a drum circle in grad school.

She flew in from Austin, and it felt like old times for the two of them, but also different. Ross still lived frugally in the Glen Park house, wore a faded red sweater all the time, and cooked his paleo diet, but he seemed happier. They had lots of sex, went dancing, and roamed the city, ending up one day on the cliffs overlooking the Pacific. In the distance, the Golden Gate Bridge rose beneath the lifting fog, catching the sun. Julia looked gamely over her shoulder at Ross and decided it was a good time to get topless. She rolled down her yellow sundress and Ross took photos. She didn’t care when a couple of hikers stumbled onto their soft-core pictorial. Ross stopped shooting and they ran off together, giggling, back toward the city.

Ross started spending more time with his housemates. One day he went to a nearby park with the girl who lived across the hall and hung out on the grass with her and her two long-haired Chihuahuas.

Marring the greenery, Ross noticed, was a piece of blue plastic stuck in a tree. A dedicated anti-litterbug, Ross climbed up to retrieve it. Back at the house he discovered he’d gotten a bad case of poison oak and needed plenty of calamine lotion for the spreading rash. He moped for days, still shirtless, but now bright red, standing out like a squad car’s flasher against his white leather couch.

($curl_error)

THE WHEELS OF the federal government grind slowly but exceedingly fine. As Ross had written in his diary in 2011, when Silk Road came to the attention of the US Senate, he knew he had awakened “the biggest force-wielding organization on the planet.” Two years later, Chris Tarbell was lying on his bed at home, with his wife, Sabrina, cooking in the other room and his kids tearing around the house so loudly he had to turn up his phone to hear the name: “Ross Ulbricht.”

Tarbell was on a conference call with the US attorney assigned to the case and an agent from Homeland Security Investigations named Jared Der-Yeghiayan. Der-Yeghiayan was stationed at the customs office in Chicago’s O’Hare International Airport and had been finding retail-size drug parcels in mail on foreign flights, all carefully wrapped, with customer service slips and return addresses to StudyAbroad.com. This, Der-Yeghiayan discovered, was a vendor on a thing called Silk Road.

Der-Yeghiayan familiarized himself with the site and learned Silk Road well enough to bust a low-level admin named Cirrus and persuade her to cooperate, allowing him to take over her account. Now Cirrus was rising through the ranks, becoming a trusted insider. Tarbell invited Der-Yeghiayan to New York to work with CY2.

Another new agent from the IRS, Gary Alford, had joined the conversation that day. As it happened, he’d been in Tarbell’s War Room earlier—Alford and the US attorney were working on a separate bitcoin case—and he’d taken a quick look at the chart. “Oh, that’s funny,” Alford said. He had worked with a different agency on Silk Road for a bit. “I had a lead in San Francisco,” he told the team. “I’ll look it up.”

Googling elsewhere for the username Altoid revealed a question about database programming posted on Stack Overflow, dated March 16, 2013, asking, “How do I connect to a Tor hidden service using curl in php?” The email listed was rossulbricht@gmail.com. A minute later, that user changed the alias to Frosty.

The IRS didn’t know what any of this meant, so that’s where it ended. The info sat in a case file until dumb luck put Alford in Tarbell’s lab, whose wall was a map where all roads led to Frosty. Der-Yeghiayan ran the name Ross Ulbricht through the federal database and found the Homeland Security report on Ross’ fake IDs. A quick search for his last known address showed that he had lived half a block away from Café Luna, the San Francisco node on his chart (the site where an administrator had logged in to the Silk Road VPN).

Tarbell was ecstatic. Finally, here was the missing piece, the end of the digital trail. Tarbell thought it was funny that these clues were sitting out in the open. In the end, one of the best law enforcement tools was Google. It seemed clear that Ross had no idea Silk Road would become such a success and was careless early on. And in the era of informational perpetuity, you only have to be careless once.

A quick tour through Ross’ social media presence revealed a digital portrait with an incredible likeness to Dread Pirate Roberts’. His LinkedIn profile was full of the same libertarian rhetoric. On YouTube he’d favorited videos from the Mises Institute, the political touchstone beloved by DPR. On Google+ (where his profile described him as “spunky, funky, not so chunky”) he asked, “Anyone know someone that works for UPS, FedEx, or DHL?” In the lab, Kiernan found code on the Silk Road server that matched lines posted by Ross on Stack Overflow.

“We found the guy,” Tarbell told his department supervisor the next day.

They put in a request to the surveillance team to send two agents to San Francisco, to get eyes on Ross. They watched him, in that house he shared with Alex, working late on encrypted wireless. Sometimes he headed out with his laptop, like practically everyone else in San Francisco, and occupied a café table to work with coffee at his side.

He did and then explained to everyone what he’d found. Some months earlier, Alford had figured that whoever had started Silk Road had tried to drum up interest on regular websites with like-minded audiences. He searched for Tor URLs around the time of the site’s first appearance and found a mention in a Shroomery.org forum on January 27, 2011, days after the Silk Road launch. A user named Altoid talked up this exciting new “service that claims to allow you to buy and sell anything online anonymously.”

An electronic wiretap on Ross’ email would require a court order—but at that point there wasn’t probable cause to search the account. So they decided to use the physical surveillance to see if they could line up Ross’ Internet usage with DPR’s activity on Silk Road. The activity matched; DPR and Ross were in lockstep. Every time Ross turned on his computer, DPR logged on to Silk Road. When he closed it, DPR logged out. Over weeks, the pattern was consistent. At his house, in cafés, in the morning or late evening, Ross and DPR were electronically aligned. When DPR would say he was taking the afternoon off, physical surveillance would watch Ross going to the park with his housemate and her Chihuahuas, lying on the grass, and getting poison oak by climbing into a tree to pull some blue plastic from the branches.

Tarbell started planning. This would be a complicated operation, seizing the site’s bitcoins undetected, taking control of Silk Road, and placing FBI people abroad—at the machine in Iceland and at another in France. Tarbell was also worried they might accidentally tip off Ross. He even wondered why Ross hadn’t bolted already. Der-Yeghiayan, online as Cirrus, was in DPR’s inner circle and knew that he was feeling extreme pressure. Tarbell thought Ross was clearly smart enough to get out while he could. In fact, Force, as Nob, was actively encouraging DPR to flee. Force had been sidelined, but his final play was to convince the digital kingpin to meet him at some airport, under the guise of providing safe passage, and take him into custody. To juice DPR’s flight instinct, Force pointed out that were he to be caught, prison would not be a safe place.

NOB: You are like one of my family. But I have to tell you that i have had several people killed who were sent to jail. It is very easy and cheap.

But Ross wasn’t going anywhere. His hubris had only grown, based on his belief in Tor and his own intellect. He thought he was invincible. Even as warning signs flashed all around him and the Feds loomed on the horizon, Ross told a potential employee that they would never get caught. “Realistically,” he said, “the only way for them to prove anything would be for them to watch you log in and do your work.”

On the evening of September 28, the FBI’s surveillance team watched DPR log off as Ross stopped working, closed his computer, left the house with his housemates, and headed for the beach.

Stay Positive

IT LOOKED LIKE a brochure for San Francisco living, a group of kids sitting around a campfire at Ocean Beach beneath a crescent moon, listening to their friend Ross play his djembe. This was the first weekend of Indian summer, that glorious time in San Francisco when everyone ventures outside and you can sit in the sand within sight of Golden Gate Park and listen to the dark waves crash on the shore. Alex opened champagne, and Ross drank Tecates and drummed along with a dude playing “Wonderwall” on a guitar in the distance.

Toward midnight, the soiree was interrupted by three cops who told them to kill their fire. No bonfires after 11, they said. The group brought the party back to their house in Glen Park, drinking on the balcony. The guys in the next house over were on their balcony too, sharing some sangria, and passed a glass to Ross. He picked up Clementine, one of his housemate’s Chihuahuas, and cradled her in his scarf like a baby in a sling, toting her around while still drinking. Ross was blotto—the only time Alex saw him drunk—and smiling.

“Let’s go inside and jam,” Alex said. And jam they did, with Alex on the piano, Ross knocking his djembe again, and some other friends singing. The music settled into a hypnotically repeating melody, as late night jams do, until everyone drifted back to their rooms or out the door. “Ha,” Ross said, hand on his drum. “I can’t keep time.”

Online, Ross’ stewardship of Silk Road was also off-balance. He recorded his troubles in his log. Law enforcement was trying to infiltrate the forums. Some big vendors were getting busted. He was hemorrhaging money, starting with a government seizure of $2 million that May from Mt. Gox, the world’s biggest bitcoin exchange, where some key Silk Road accounts were held. Unrelated, Redandwhite convinced Ross to give him $500,000 and then disappeared. Even his friend Nob was still making veiled threats about how easy he would be to kill in jail.

Amid the chaos, DPR did talk to Libertas, one of his most trusted admins, about taking over Silk Road in case of emergency, but he never gave him server access. As he tried to keep his fingers in the dike, DPR confided his worries to Cirrus, who by the end of September was briefing a massive FBI team in San Francisco alongside Tarbell and Kiernan on the looming arrest of Ross Ulbricht.

If Ross knew the noose was tightening, he didn’t show it. In the days after the Ocean Beach party, he worked at his standing desk and called Julia in Austin, telling her he was going to visit in November. She sent him sultry photos, naked and dancing, as a preview. That Monday night, Ross wrote in his diary: “Had revelation about the need to eat well, get good sleep, and meditate so I can stay positive and productive.”

/Mastermind

THE DINING ROOM of the San Francisco Airport Marriott was nearly empty at 6 am on Tuesday, October 1, 2013, when Tarbell met Kiernan and Der-Yeghiayan for another mediocre breakfast. Tarbell hadn’t slept much since arriving in San Francisco two days earlier. He and his New York team were edgy, having been in position waiting on the right moment. There was, as usual, a bureaucratic complication. Silk Road was Tarbell’s case, but he and CY2 were visitors at the pleasure of the San Francisco FBI office, and it was their assistant special agent in charge who had, as cops say, “designed the arrest.”

In classic form, the local FBI wanted to mount a dramatic raid on Ross’ house. Tarbell didn’t like this idea. He was worried about repeating the mistake made during his first big cybercrime case, when they arrested a hacktivist named Jeremy Hammond in Chicago. There, a SWAT team charged into Hammond’s apartment throwing flash grenades, immediately alerting Hammond in the back room, who shut the lid of his laptop, encrypting it forever.

This kind of operation didn’t need SWAT, Tarbell thought. It required finesse. To prosecute a cybercrime you needed direct evidence, which centered around Ross’ machine. Tarbell wanted to get Ross in medias res, with “fingers on the keys,” as they say in the trade. Tarbell had read in DPR’s chats about how secure his system was, how one keystroke would erase it all. There was no margin for error. They needed complete surprise.

Still, the assault strategy remained in place. “Thank you for your input,” the local FBI supervisor had told Tarbell. “Now here is the plan.” There would be three SWAT teams, one for each floor of the house. They would hit at dawn, gaining “fluid entry.” They couldn’t promise, but they would try to catch Ross while he was online.

“These are the fastest SWAT teams,” the supervisor said.

“But it doesn’t matter,” Tarbell said. “No one is fast enough.”

The arrest had been scheduled already, but Tarbell kept asking to delay so that they could catch Ross at one of his cafés. They’d seen him out working once but didn’t have “assets in position.” Tarbell was granted one delay, but that was it.

“Your equity is used up,” the San Francisco chief said. “No more favors.”

The SWAT assault was scheduled for 5 am on Thursday. The entire tactical force—dozens of agents—had gathered at an FBI cybercrime facility an hour south in San Jose, prepping their final review.

 

TARBELL DIDN’T MAKE it to San Jose. He and Der-Yeghiayan stopped by the San Francisco federal court building to amend the search warrant for Ross’ house. Kiernan and another officer were still in San Francisco as well, near Ross’ house in Glen Park. They had stayed in position, hoping, praying that Ross would come walking out that door with his laptop bag over his shoulder.

Tarbell decided to meet his team at Bello Coffee & Tea, a place Ross frequented just next to the Glen Park Branch Library. It was 1 pm. Sitting on the bench outside the café, Der-Yeghiayan went on Silk Road as Cirrus and saw that DPR was also logged in. Physical surveillance said Ross was still at home. Tarbell worried that in this leafy patch of San Francisco, he and his completely cop-looking crew, sitting around one laptop, would stand out. The group scattered and tried to act casual. Der-Yeghiayan went to a nearby market but then noticed his computer was nearly out of juice. So he went back to Bello, only to find the place full, with no free outlets. Tarbell returned to the bench, getting a chance to do some more worrying.

At 2:45 pm, Der-Yeghiayan saw DPR log off. A few minutes later, Tarbell heard from surveillance: They had eyes on Ross leaving his house. He was wearing jeans and his red sweater and walking east. And carrying his computer. “He’s on the move,” they said.

Holy fuck! Tarbell thought. He’s coming. CY2 scattered again, this time in a giddy panic, zigzagging for cover like in a game of hide-and-seek. Tarbell left Der-Yeghiayan, still holding his laptop, to head down the street in the direction of Ross’ house. He felt high from the adrenaline. He didn’t realize Ross was on top of their position. Tarbell was rereading Ross’ description from the surveillance team when he looked up and saw Ross heading directly toward him. It felt like slow motion, coming face-to-face with the man he’d been tracking for months, resolving him from digital obscurity into a real live person walking up Diamond Street. Tarbell worried he’d get made. He was trying to act all Mister Undercover, but, Jesus, did he look like a cop. Ross walked right past him toward the café.

 

FROM ACROSS THE street, Der-Yeghiayan saw Ross duck into Bello. This seemed promising; they’d been hoping he’d sit down somewhere and log on to Silk Road, giving them an opportunity for a red-handed arrest. But Ross quickly left. It was probably the lack of outlets, Der-Yeghiayan imagined, looking at his own computer, which now had only 22 percent battery power left. A scary number, as he had to be connected online to verify DPR’s presence. Ross walked into the library next door.

Oct 1, 2013 2:53 pm

From: Chris Tarbell

Subject: Re: Ross Ulbricht

By email, Tarbell alerted his team. That message cc’d the whole operational group, which was midbrief, preparing for their raid, when they learned that the little squad of out-of-towners had ventured off-piste and cornered their man in the Glen Park Library. “We got him,” Tarbell said when his supervisor called from New York. “I’ll call you back in 10 minutes.”

With Der-Yeghiayan’s dying laptop, they watched Ross log on as DPR, then navigate into the marketplace, then the forum, then the elite admin chat where Cirrus was waiting to say hello. Tarbell knew the chief down south had surely mobilized. Fifty tacked-out federal agents were racing up Highway 101.

The cavalry was coming, and Tarbell wanted to get Ross before sirens showed up.

Kiernan and another agent had been in the library when Ross walked in. He went right by them and continued unaware past the periodicals and reference desk, beyond the romance novels, and settled in at a circular table near science fiction, on the second floor. The other agent assessed the tactical landscape up there, which was tough: Ross was sitting in a corner, with a view out the window and his back toward the wall. There was no obvious approach. It was Kiernan’s job to get Ross’ laptop, and it looked tricky. “Your sole job is to get the laptop,” Tarbell had drilled Kiernan. “Get the laptop. That’s why you’re here. Get the laptop. And keep it alive.”

 

TARBELL AND DER-YEGHIAYAN joined the action in the library, taking a spot on the stairs at a landing. Der-Yeghiayan was alarmed at how fast his battery was draining, but he kept communicating with DPR, making sure he logged in to the admin panel. Tarbell peered over the last step but couldn’t see much. Somewhere in the stacks was the other agent, but Tarbell wasn’t sure where. Everyone was communicating electronically, trying to coordinate, caught blind by the moment. Minutes ticked past. Der-Yeghiayan and DPR still chatted. His battery dropped further. Tarbell heard from the plainclothes surveillance team—they were in the library too. Tarbell didn’t know where exactly, because he didn’t know what they looked like. (Such is the very low profile kept by field surveillance.) A few miles away, the giant squad of SWAT teams was approaching San Francisco. All the local supervisors were in that armada, so technically Tarbell was in charge here on the ground. He took a deep breath and sent a message: “Let the guy run if you have to, but don’t let that computer close.” This was the moment. Tarbell didn’t know it, but the surveillance agents had designed a new arrest on the spot. He had no idea what would happen when he took a deep breath and told everyone: Go.

What unfolded next was a piece of improvisational theater. At 3:14 pm, DPR was typing away, writing to Cirrus. Just then, a middle-aged woman and man came toward Ross, ambling along in the kind of semihomeless shuffle you might often see in a San Francisco library. “Fuck you!” the woman yelled when they were directly behind Ross’ chair. As if they were a deranged couple about to fight, the man grabbed the woman by the collar and raised his fist.

Ross turned around for just a second, during which a hand reached across the table and grasped Ross’ Samsung. The petite, unassuming young Asian woman sitting across from Ross this whole time was, to everyone’s surprise, also an FBI agent. Ross lunged for his machine, a hair too late, as she turned like a quarterback for a quick handoff to Kiernan, who appeared out of nowhere—as instructed—to get the laptop. It took less than 10 seconds. From afar, Tarbell was astonished by the elegant choreography of the whole thing. It looked like the police procedural version of a tight jazz quartet.

While Ross was cuffed, Kiernan immediately sat down with Ross’ PC. It was open. He could see everything. The machine ID was Frosty. Ross was logged in to Silk Road as an administrator under an account called /Mastermind.

Kiernan also saw that Ross was torrenting some television. Of all things, he was downloading a segment from the previous night’sColbert Report—an interview with Vince Gilligan, creator of Breaking Bad. The series finale had just aired, and Gilligan talked about the central theme of the show, how ordinary people are capable of terrible things. It took just two years for Walter White to turn from good-natured science teacher to liar, murderer, and master of a drug empire. Had Ross not been arrested he would have watched Gilligan say that yes, of course, Walter was doomed from the start. And everyone knew it but him.

 

Halfway across the Atlantic, Yum was with the Icelandic authorities, poised to enter the Thor Data Center and “escalate privilege” over the Silk Road marketplace and bitcoin servers. Then the team in France would take over Silk Road’s redirect server. Tarbell barely noticed the pleasant afternoon, instead staring at his BlackBerry, monitoring the constant scroll of messages tethering this whole delicate operation together.

TARBELL STOOD WITH Ross for the first time, searched him, and put him into a surveillance van, where he read him his rights. Ross showed only a slight quiver in his lip and asked to see the charges. Tarbell presented him the warrant for Ross Ulbricht, aka Dread Pirate Roberts, aka DPR.

The rest of the force started arriving, black Suburbans and SWAT vehicles with lights blazing. Soon there were uniforms everywhere. Even though Tarbell’s improvised bust was a complete success, cops are cops, and the local FBI was fuming at Tarbell’s departure from protocol. He and his team, considered computer dorks back home in New York, had the strange satisfaction of being called “fuckin’ cowboys” by a swarm of guys bristling with gear and guns. Tarbell took it as a compliment. Then he put Ross in an FBI cruiser bound for the local jail.

Tarbell called Yum in Iceland to set that phase in motion. Yum shut down communication between the machine in the Thor Data Center and all the others around the world and then simply “changed possession” of the bitcoins by redirecting the digital pointers—this is how ownership of the currency works—from Silk Road to an FBI account. And voilà: All your coins are belong to us.

In France they discovered a digital booby trap: To redirect the Silk Road site itself required a delicate data process that could shut the box down; if restarted, the server was programmed to delete its key, basically self-destructing. But the trap was discovered, and gingerly evaded, and the machine succumbed. Thereafter, the Silk Road welcome page read: THIS HIDDEN SITE HAS BEEN SEIZED BY THE FEDERAL BUREAU OF INVESTIGATION. Within minutes, Reddit erupted. “Is this a joke?” someone posted, along with plenty of WTFs.

The arrest was such a coup that the Justice Department wanted to publicize it. They’d planned on staging a press conference in Washington, with attorney general Eric Holder himself, to make a strong statement about the government’s ability to take on cybercrime. But, as it happened, Ross was arrested on day one of the dramatic government shutdown, when one of his heroes, Rand Paul, along with other senators, held the federal budget hostage over the debt ceiling and forced Washington to go dark. There would be no Holder, no press conference, no government at all to celebrate its defeat of this libertarian, lawless challenge. The only public notice of Ross’ arrest was the release of the FBI’s initial 39-page complaint signed by Tarbell, cementing his new public persona as DPR’s digital Van Helsing.

In the car, Tarbell and Ross found themselves alone in the backseat. Tarbell had read so much about him, it was kind of like seeing an old pal. Tarbell talked about Ross’ life in a way that made it clear how much he knew. Ross was talkative but cagey. He seemed relaxed, as if relieved. Not in being caught, but just being with someone who possessed his secret. In front of Tarbell, he could be both Ross and DPR. He admitted nothing to Tarbell, but after a natural pause in the conversation, Ross said, “I don’t suppose $20 million can get me out of this?” It might have been the most authentic moment in Ross’ life in more than two years.

“No,” Tarbell said. He couldn’t resist needling him. “Even if it could, what about this guy?” He pointed at the driver, another FBI agent. “Have to take care of him too, right? How much money do you have?”

Ross looked ahead as they weaved toward the jail.

IN A VAN that doubled as a mobile lab, Kiernan worked forensics on Ross’ computer. He quickly found a mountain of evidence: a list of all the Silk Road servers and the names Ross had purchased them under, 144,000 bitcoins (more than enough to cover that $20 million bribe), a spreadsheet showing Silk Road accounting (including a capital-equipment entry for the purchase of that very laptop), and those diaries Ross kept, which detailed his hopes, fears, and foibles in operating a vast criminal conspiracy.

Kiernan also found a file called emergency .txt, with an unrealized escape procedure:

Destroy laptop hard drive and hide/dispose

Hide memory stick

Go to end of train

Find place to live on craigslist for cash Create new identity (name, backstory)

At Ross’ house, agents found a USB drive containing some Silk Road programming, but beyond that, little else. When Alex and the other roommates got home, they found the warrant on the coffee table.

Alex visited Ross in jail. He expected him to be shaken, but Ross was the same as always. He would soon be transferred to New York to face a seven-count indictment. It was hard for Alex to believe that the new guy in the extra room, his pal, was also the guy described in that warrant. The thought of Ross being guilty of even tripping someone, much less ordering a murder, seemed unlikely. He was always such a chill dude.

All Rise

ROSS WAS ARRAIGNED in federal court in New York a few months later, still seeming pretty chill. He pleaded not guilty. Like Alex, Ross’ friends and family couldn’t believe the charges. They were first shocked, then incensed. There emerged a familiar refrain: Ross was such a nice guy. There must be some mistake. Ross’ lawyer, Joshua Dratel, a seasoned, high-profile defense attorney who took on tough cases, made the same argument. His letter asking for bail was a moving collection of testimonials on Ross’ behalf: “good role model,” “reputation for fulfilling his obligations,” “fearless embrace of making the world a better place for everyone.” But the judge, citing flight risk, denied bail altogether.

Online, Ross became a cause célèbre. The libertarian and cypherpunk communities naturally felt that their champion had been martyred. The charges were ginned up, they thought, retribution for Ross having the temerity to challenge the government itself. Many a Reddit thread overflowed with outraged chatter and meticulous analysis of what the community insisted was overreach, flawed evidence, or a frame job. A solidarity site appeared: Freeross.org.

Ross and his attorney prepared a defense that basically amounted to “Wasn’t me.” They chose to occupy that narrative gap of uncertainty made possible by the ambiguity of identity online. Dread Pirate Roberts was just pixels, they said. Everyone knew there were many DPRs, they argued, returning to the lore of Silk Road and the symbolism of the alias.

It was a powerful idea. In the months leading up to the trial, the defense created a speculative froth about the very nature of identity, suggesting that Silk Road was an ongoing mystery. After all, everyone loves a whodunit. The case became like a crowdsourced mystery theater, with so many potential question marks hidden in the numbers and code.

Then the trial started. And the conspiratorial mindset was no match for clear, hard, overwhelming evidence. The courtroom was packed with Ross’ family, supportive spectators, and press as the biggest cybercrime trial in years unfolded in the federal district court building in downtown Manhattan. But armed with hundreds of exhibits, the prosecutors for the US attorney’s office presented an efficient, detailed case. They showed the diaries. Der-Yeghiayan explained how they caught Ross logged in as /Mastermind. They read aloud from DPR’s chats, stored on Ross’ computer, presenting the odd spectacle of gray-suited government lawyers addressing the court with choice narrations like “Squid gave me the support link, just let me know when I have access.” Outside, a vigil of protesters held signs, some reading “FREE ROSS”.

It was a quick trial, 13 court days, faster than expected. Observers were surprised at the volume and detail of evidence, the kind you rarely see. To the end, Ross’ lawyer, Dratel, claimed it was a case of mistaken identity. (Like most criminal defendants, Ross himself didn’t testify.) Or rather, a qualified case of mistaken identity. Dratel caused quite a stir in his opening statements by admitting that Ross had indeed started Silk Road, but then quickly sold it off to some other unnamed figure. The attorney also claimed that Ross was later duped by this savvy character back into Silk Road to take the fall as the FBI closed in. To account for the vast sum of bitcoin wealth, Dratel explained that Ross was just a good currency trader. Then Yum took the stand to demonstrate precisely how Ross received all the bitcoin commissions from Silk Road during the entire tenure of Dread Pirate Roberts.

Ross’ family was surprised to hear the admission that he’d created Silk Road. Reporters could see it on his mother’s face. Lyn Ulbricht was a sympathetic figure, a caring mother leading a vigil for her son. She was smart and articulate and had become a vocal public figure in support of Ross. Throughout the trial she maintained that the jury would set Ross free.

This was more than a mother’s love. Lyn, like many supporters, just believed Ross. Which was understandable, to some degree, as Ross’ story was one of fluid identity. The prosecution said that Lyn’s good-natured son had turned into someone else. Lyn said that this someone, if he or she even existed, had been projected onto her son. Ross said nothing and remained a willing cipher, allowing everyone to project an identity onto him: To Alex, Ross was the cool new roommate; to Julia, a passionate lover and inspiration; to his family, the perpetual Eagle Scout; to Force, an unlikely friend in the night; to Tarbell, a smart kid defeated by his own arrogance. To the Southern District of New York US attorney’s office, Ross was simply the criminal conspirator Dread Pirate Roberts.

The likeliest reality is that Ross was all of those things. The open-minded seeker who conscientiously tried to pluck trash from a tree was Ross. As was the feverish visionary creating a virtual empire at any cost. Neither truth invalidated the other. Ross and DPR can (and did) coexist.

Amid all the murder minutiae, it’s possible to lose sight of the young idealist who sat down and coded his way into history. He was right about the war on drugs: It is a failure. And Silk Road was a perfectly natural response. There was a lot to like in the site’s original idea of an economically mediated utilitarian society. It is still easy to appreciate that Ross, the one who believed in choice and happiness. “Our basic rules are to treat others as you would wish to be treated,” Ross wrote as DPR on Silk Road.

 

Ross, who declined to be interviewed for this story, was not charged with any murders. The case involving Green, which came out of Baltimore, was a separate indictment. (It is still pending.) The New York case dropped the five other murders after further investigation revealed that the whole thing was likely an elaborate catfish-as-blackmail scheme that snookered Ross out of a lot of money. But in all cases, the prosecution argued, Ross believed he was executing people, even receiving photographic evidence faked to prove it. For dramatic effect, the prosecutors read aloud selections of Ross’ conversations where he sounded like a heartless mafia boss.

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