American Kingpin

by Nick Bilton

  After two weeks on the island, with his citizenship application now going through the system, it was time for Ross to return home.

  The trip back to the United States took almost two days, Ross finally touching down at San Francisco International Airport after the four-thousand-mile journey.

  On the surface it seemed that the trip had gone unnoticed, that the Dread Pirate Roberts had slipped in and out of the United States without detection—which was true. But Ross wouldn’t be so lucky.

  As an American customs official swiped his passport into a digital scanner, Ross William Ulbricht didn’t know that his name and where he had just traveled from were now being converted into a million ones and zeros. Or that this information was now traveling from the customs official’s computer across the country, in mere milliseconds, through the same wires that enabled people to buy and sell drugs on the Silk Road, and landing in a database that belonged to the U.S. Department of Homeland Security.

  Chapter 38

  CARL LIKES DPR

  On paper the Marco Polo task force was an all-star team of talent, composed of Carl Force at Baltimore’s local DEA and other agents hailing from various local departments of the federal government, including the postal service to help with seizures and the Secret Service to trail the money (Carl, of course, was in charge of the drugs). In the months since the task force had been realized, the group had proclaimed that it would be the first in the United States to crack the Silk Road case.

  Yet almost from the start the Marco Polo crew was entangled in disorder.

  First there were the serious turf wars that emerged. If you were the one who took down the site, you’d be lauded as a hero forever. This case could change a career. As a result, some on the task force were backstabbing more experienced agents to try to gain leadership control of this hot new case (and in many instances were succeeding).

  The cherry on top of that chaos was Carl Force, who wouldn’t take orders from anyone, even his own boss. More often than not, when requests came in from others on the task force, Carl just ignored them altogether.

  This wasn’t the first time in his career that Carl had acted this way. During one of his last real-world undercover operations, years before he started playing the lead role of Nob the drug smuggler on the Silk Road, he had gone rogue on a case and soon found himself in a lot of trouble with the DEA, and his wife.

  Back then Carl was working undercover among a group of drug dealers when he started to go deeper and deeper into their clandestine world with the hope that they would trust him more, which could lead to a big bust. But Carl was slightly too good at the undercover part of the job. While he was manipulating the people he was trying to arrest, he started to blur the line between cop and friend. At nightclubs he would get blackout drunk with the people he was monitoring. When women approached him and his new friends, Carl didn’t shoo them away to focus on trailing his subjects but rather embraced these bad girls with open, inebriated arms. Before long the line between pretend drug dealer and churchgoing DEA-agent dad faded so much that he had to quit the undercover work and go off to rehab, eventually landing, sober, with the desk job in Baltimore.

  Years later, when Carl decided to become Nob, he reasoned that this was a different kind of undercover job. He was safe from the temptations of the underworld because he was behind a computer. And yet, just as in his old days with the drug cartel, Carl found himself increasingly drawn into the world of the Dread Pirate Roberts. After a day in the DEA offices, Carl would go home, straight into the spare room of his old Colonial house in Baltimore and onto the computer to converse with the man he was supposed to be hunting.

  The room where Carl sat typing away wasn’t much to look at, with a single bed and a bookcase that had once belonged to his grandfather. Here Carl would sit in an old brown and white lounge chair, his legs stretched out on the ottoman, as his online personality, Nob, chatted with DPR about everything and anything, and Pablo, the family’s mentally deranged cat, which hated being touched, watched from the bed.

  At times they talked about family, with Carl saying prayers for Dread and his loved ones. During other occasions, they talked about their health.

  “Tell me about your diet,” Carl asked.

  “Minimize carbs,” DPR replied, “no bread, no pasta, no cereal, no soda. I eat lots of hard boiled eggs.”

  One reason Carl was able to chat with DPR for so long was because it was apparent to him that Dread was lonely. All that time behind a mask must have taken its toll on the leader of the Silk Road, and DPR evidently sought solace from the people he was connecting with online. Carl astutely reasoned that he could use this to his advantage, coaxing the leader of the site to share more, and enticing him to be Nob’s friend. A little manipulation here, some deceit there, and the Dread Pirate Roberts would be eating out of Carl’s hand in no time at all.

  Yet the attempt was backfiring, not because Carl wasn’t getting close to DPR, but rather because he was getting too close to him. They would talk for hours about relationships, music, and the future of the drug trade.

  For Carl, who had been fighting the war on drugs for more than a decade and getting nowhere, arresting one dealer only to see another take his or her place had gnawed at his purpose in the world. Now the arguments the Dread Pirate Roberts was making about the war on drugs were actually starting to make a little sense. Maybe the answer to all this violence and waste of government resources and the hundreds of thousands of people rotting away in jails was to legalize drugs. Maybe Carl was on the wrong side of the war.

  Maybe, maybe, maybe.

  Somewhere along the way of those maybes, Carl started to become enamored with Dread. He started greeting DPR with affectionate salutations. “Hello my friend,” he would write. “Is all well?” At other times he offered, “Stay safe,” and each night that they spoke, he told DPR to “sleep good.” There were compliments: “You are the most interesting man in the world, stay thirsty my friend!” And Carl even joked once, “I love you.” To which DPR replied, “Yer making me blush :).” Soon after that exchange, Carl started to sign his letters to DPR with an affectionate “Love Nob.”

  Sure, part of this was Carl being undercover, but part of it wasn’t.

  As the relationship progressed, in addition to trying to draw out the leader of the notorious drug and arms Web site, Carl started antithetically offering advice on how DPR could camouflage himself even more. “You can do one of two things,” he wrote to Dread. “Move to another country where you are safe from the laws of your native country or come to grips [with the reality that] there is always the possibility of getting caught.”

  He counseled DPR on looking into alternative passports and possibly finding a backup place to live. Carl also taught him how international drug-smuggling routes worked through “dead drops,” where dealers leave drugs or guns in a location like a storage locker at a train terminal and then give the buyer the locker combination so they can grab their stuff and leave the money behind without the two ever meeting in person. The perfect way for the Silk Road to avoid the mail system. Finally Carl gave DPR advice about getting a lawyer.

  Carl wasn’t always blurring the line of DEA agent and pretend drug dealer. There were times he did things by the book, including helping his co–case agent Mike McFarland from HSI Baltimore order drugs off the site from low-level dealers and then arresting those sellers. Over the summer they detained a few people and took over their accounts with the goal of trying to corner others. In one instance they arrested a man in Baltimore who sold meth on the Silk Road. In another they busted a man in Lincoln, Nebraska, who sold phenazepam, bromo blotters (which were similar to LSD), prescription meds including Xanax and Valium, and, for an added bonus, guns.

  But even during the moments when Carl was doing his job as a cop, he would sometimes become a rapscallion. In one instance he teamed up with another agent, Shaun Bridges, who worked for t
he Secret Service and who had joined the Marco Polo task force to help follow the money. The two agents tried to recruit the National Security Agency to help in their hunt. Bridges had an intimidating look to him, with thin, squinty eyes, a black goatee, and short buzzed hair that made his ears pop outward. There was something about him that seemed to say, Be careful with this one, but Carl didn’t see it.

  The NSA, or “No Such Agency,” as it was unofficially called, was rumored to be able to crack into any secure computer on the planet. Carl reasoned that the NSA could help him break Tor and find the Dread Pirate Roberts. While everyone else on the Marco Polo task force knew the agency didn’t touch drug-related cases, Carl and Shaun were determined to get it involved. So one day, without the knowledge of any of the other agents, the two men set up a secret meeting with one of Shaun’s contacts at the NSA. They didn’t want a paper trail, so everything was done in person.

  The NSA analyst they met with, while sympathetic to their plight and the numbing hunt for the Dread Pirate Roberts, informed them that the NSA’s mandate was only to go after targets that could harm the security of America. “Sorry, we can’t help you,” the analyst said. Oh, and by the way, this conversation never happened.

  But the two agents weren’t going to give up so quickly, so Shaun presented an alternative idea to Carl: “Let’s start trying to buy explosives on the site!” This way, he said, they could show that the Silk Road and other Dark Web sites could be used to harm America.

  “I’m in!” Carl responded gleefully. When Carl told his boss, Nick, he was warned not to go there, noting that “bombs” were not part of the DEA’s mandate, in the same way that drugs were not part of the NSA’s.

  But Carl was in charge, at least in his mind, and no one was going to tell him what to do. So he and Shaun explored buying pipe bombs online and having them shipped to an undercover government PO box, where they would be able to show the NSA analyst that the Silk Road could be used for an attack on U.S. soil. Soon they realized a random discovery of a couple of pipe bombs in the mail might cause a bit of a stir in the postal service, and the plan was halted at the last minute.

  When that detour didn’t work out, Carl returned to the goal of befriending DPR, and in doing so, would say whatever he wanted to the site’s leader.

  Not surprisingly, almost anyone who read the chats between Nob and Dread started to question why they were so detailed.

  On more than one occasion Nick, Carl’s boss at the DEA, saw the conversations between the two men and was livid. He would call his underling into his office, slam the door shut behind him, and, amid the din of heavy metal music, erupt into an apoplectic rage. (Carl found glee in pissing off his boss, so he sat there undeterred.)

  “I’m just doing this stuff to get close to him,” Carl told Nick unapologetically, which was half true. “I need to develop trust with DPR.”

  It was hard to assert that this approach wasn’t working. There was an argument to be made that Carl was going to bring down the Silk Road before other agents, and it was becoming apparent that there were plenty of others in the U.S. government who wanted that glory, including (as Carl had heard) Jared Der-Yeghiayan over in Chicago. It seemed perfectly fine to overlook Carl’s peculiar interaction with DPR if it meant the Marco Polo crew was going to win.

  Which is why when Carl approached his team about doing a controlled drug buy that would be facilitated by none other than DPR himself, no one questioned if it was a bad idea.

  The plan Carl came up with was to have his online persona, Nob, sell a bulk order of cocaine or heroin to a buyer. And as he suspected, the Dread Pirate Roberts was happy to help expedite the sale.

  “How much can you sell 10 kilos for?” DPR asked one afternoon.

  Of heroin?

  Yes, of heroin.

  Nob, playing the part, explained that he had only “Mexican brown H, not china white” but that the first ten kilos would be $57,000 apiece, or just over half a million dollars. If the sale went well, he would drop the price to $55,000 a kilo, and then to $53,000. But what he could sell for less money, Nob explained to Dread, was a kilo of cocaine.

  “All right,” DPR wrote, he would find a buyer for a kilo of coke.

  And so, as Dread went off to facilitate the sale, it was starting to become unclear who would be on the other end of that transaction. Would it be the churchgoing DEA-agent dad who wanted to capture the Dread Pirate Roberts and get the glory of bringing down the most notorious drug dealer of his career? Or would it be Nob, the fearless drug smuggler who wanted to help DPR find safe passage along the Silk Road?

  Chapter 39

  KIDNEY FOR SALE!

  Ross stood in his bedroom, his white sheets rumpled on the bed, as he buttoned his pink-and-green-checkered shirt before heading out on another San Francisco adventure.

  Over the past few months he had explored every crevice of the Bay Area. On some days he had ventured south to Bernal, where he climbed to the peak of a hill. He took long walks past the piers with sunbathing sea lions. He had gone north with his roommate and best friend, René, over the Golden Gate Bridge to Marin, where they hiked the trails amid the redwood trees, clambering through the salty fog and stopping every few feet to marvel at thousand-year-old trees that seemed to almost touch the heavens. Between explorations Ross went on boating trips with friends through the choppy waters of the bay, brushing past Alcatraz, the notorious prison that had once been home to Al Capone, the American gangster who fought the U.S. government during Prohibition.

  But one of the more memorable experiences of his time in San Francisco happened on a Thursday afternoon in early December, when Ross and René happened upon the Contemporary Jewish Museum in the South of Market area of the city.

  Homeless people, mostly drug addicts who had fallen on hard times, lined the streets, pushing their lives in carts from one soup kitchen or rehab center to the next, past the big glass buildings where those billion-dollar start-ups grew larger and more powerful by the hour. It was chilly that day, and a light sprinkle of rain fell from the sky as the two friends walked inside the museum. They wandered around the brightly lit, cavernous rooms until they came upon a metal box the size of a shed on whose side the word sTORYcORPS was written in big bubbly red letters. Ross and his friend pulled open the door to the metal box and sat down in front of two microphones. A red light soon came on to indicate that what they were about to say to each other was going to be recorded.

  Ross began, introducing himself and noting, “I’m twenty-eight years old.” His voice was calm and crackly.

  The recording they were about to make was part of a National Public Radio experiment; the box they sat in would travel the country, enticing Americans to tell their stories for posterity, to try to capture the change the United States was going through at the time. Some of the recordings people had already done in other parts of America were sad, like the two parents who told the story of their young son who had died because he couldn’t get a bone marrow transplant for a fatal disease. Another man talked about his experience being hit by a roadside bomb while serving in Afghanistan. And other stories were more uplifting, like the couple who fell in love during Hurricane Katrina.

  It might not have been the wisest thing for Ross to draw attention to himself. But if on the Silk Road the Dread Pirate Roberts got to speak the truth about society all the time, why shouldn’t Ross be able to do the same thing in this world? No one would ever be the wiser that the man about to speak into the microphone was actually two men.

  Ross and René were instructed to talk to someone who might listen to their conversation two hundred years in the future. They began discussing how they had ended up in San Francisco. René had come for the “start-ups and the money,” he said. Then it was Ross’s turn to tell the story of how he had ended up inside this metal box.

  “I was living in Austin, Texas,” Ross said, and then he trailed off, as if he were
traveling back there in his mind. “And, ehm,” Ross continued, stuttering slightly as he stared off into the distance. “And, ehm,” he said again.

  René looked back, waiting for his friend to finish the sentence, seemingly oblivious to where Ross’s mind had just wandered off to.

  As close as Ross had gotten to René, he kept the promise he had made to himself a year earlier. He would never tell anyone else in the real world about the online world he had created. He had learned that bitter lesson with Julia.

  It had been difficult hiding the truth. Friends in the real world would say things to him like “Why don’t you try this business idea or work on that app?” to which Ross would simply say, “Good idea, dude. I’ll think about it.” But, as he told his employees on the site, he just wanted to “scream at them, ‘Because I’m running a goddam multi-million dollar criminal enterprise!!!!’”

  Lying came at a price. To separate those two worlds, and to justify the actions he had to make in each—telling stories to his family and friends in one and making resolute decisions with vast repercussions in the other—the man in the pink-and-green-checkered shirt had become incredibly adept at separating the life of Ross Ulbricht from that of the Dread Pirate Roberts.

  As Ross he would go on these walkabouts with his friends (or alone), and the biggest decisions he had to make each day were where the adventure would begin and what he would eat for lunch. When he stepped into the role of the Dread Pirate Roberts, he hid Ross away, and DPR reveled in the power that came with dictating the rules of a world in which hundreds of thousands of people roamed. He was the one who decided who got to stay on his island and what they could and could not do while they were there. And DPR, while seemingly the same person as the sweet Ross his mother had raised, was able to make tough decisions that a younger self would have cowered away from.