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  • Writer's pictureArtee

The Untold Story of Silk Road, Part 1

Updated: Oct 27, 2018

Hacking is becoming less about Computer Science and more about Human Behavioral Science. How an individual can slip from being an idealist to choosing to take away a person's life. **Reader discretion is advised.** #FullMetalFreedom

“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.

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.

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.”

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.

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.

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.”

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.”

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!

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.

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.

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.

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?”

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.

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.”

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.”

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.



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?”

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.

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.”

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.

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.

“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.”

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.

“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.

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.

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.

Home alone with his two Chihuahuas, Green cried like a baby. 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.

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: 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.

Read the story’s conclusion, “Part 2: The Fall,” here

This article includes reporting by Nick Bilton, whose book on the Silk Road case will appear in 2016.

This story appears in the May 2015 issue.

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