American Kingpin

by Nick Bilton

  Ross opened a text document on his computer and created a file he called “Emergency.” He then began writing a list of things he would need to do in the event that something went terribly wrong. A doomsday list.

  “Encrypt and backup important files on laptop to memory stick; destroy laptop hard drive and hide/dispose; destroy phone and hide/dispose,” Ross wrote. “Find place to live on craigslist for cash. Create new identity (name, backstory).”

  But he also knew that if the day arrived when Ross and DPR did have to go into hiding, simply finding a place on Craigslist and changing his name wouldn’t be enough to protect him indefinitely. He would have to come up with a safe place to flee to. Possibly even another country. A country that embraced pirates and would take in Ross Ulbricht and the Dread Pirate Roberts and their millions of dollars in wealth and keep them both out of reach of the U.S. government.

  Chapter 36

  JARED’S DEAD ENDS

  This is so frustrating! Jared thought.

  He held on to his son Tyrus’s hand as he continued walking down the aisles of the Barnes & Noble in Lincolnshire, Illinois. They trudged up one row of books and then down another. Every few feet Tyrus, who was now three and a half, looked up at his dad as Jared searched intently for something among the stacks.

  “Hello,” a chirpy woman at the information counter said to them finally. “Can I help you find something?”

  “Erm,” Jared said, “I’m looking for some books on the Mises Institute.” He looked around to make sure no one had overheard what he was asking about. The last thing Jared wanted to do was get into a discussion with a random person on this topic.

  “The My Says Institute?” the woman asked loudly, looking down at her computer.

  “No, it’s Mises, M-I-S-E-S,” Jared whispered. “It’s a libertarian think tank that focuses on Austrian economics and . . .” He trailed off, realizing this probably made no sense to the woman in front of him. After all, this made no sense to Jared.

  But still, he needed these books for the next phase of his investigation, which was starting to stall.

  Since the beginning of the year, Jared had seized almost two thousand new shipments of drugs coming into the country, all by figuring out what each package would look like, and in doing so had disrupted the Silk Road as best he could. Jared had also arrested and detained a few dealers on the site, including one of the busiest, who sold ecstasy and other drugs from the Netherlands. And he had subsequently taken over some dealers’ accounts on the Silk Road, gaining a better understanding of the inner workings of the operation.

  But he was still no closer to unearthing the founder of the site. So after finding himself circling around in too many online cul-de-sacs, Jared decided he would try to get inside the mind of the Dread Pirate Roberts, which was why he was standing in the Barnes & Noble in Lincolnshire, awkwardly asking about the Mises Institute.

  In recent weeks he had sat at his desk, a Rubik’s Cube always spinning in his hand, as he read all of the online postings by the Silk Road’s creator, looking for similarities in the author’s language. As the site had grown, DPR’s message had become more brazen. While at first the founder’s idea had been to make drugs legal, more and more he wrote about how terrible the U.S. government was, and how it was a place for the abuse of power. In one post DPR gloated that the “state is unable to get its thieving murderous mitts on [the Silk Road].”

  Based on all of his writings, Jared had started to build a profile of who this Dread Pirate Roberts might be. He was likely very educated, young, not rich but not poor either, and while he wanted to destroy the American legal system, he was also doing this for the money. DPR had even admitted this in postings on the site, noting that “money is one motivating factor for me. . . . I also enjoy a few first-world pleasures that I feel I have earned. . . . Compared to most I know, I still live quite frugally.” But from Jared’s readings it appeared that DPR also believed that what he was doing was making the world a better place. “As corny as it sounds,” Dread had written online, “I just want to look back on my life and know that I did something worthwhile that helped people.”

  Jared, trying to find things that others couldn’t see, started to analyze DPR’s speech patterns. For one, Dread used the word “epic” a lot, which showed that he was likely younger. He also used emoji smiley faces in his writing, though he never used a hyphen as the nose, writing them as :) rather than the old-fashioned :-). Yet the one attribute about DPR that stood out to Jared was that rather than writing “yes” or “yeah” on the site’s forums, Dread instead always typed “yea.”

  DPR was constantly recommending books to his followers—a litany of literature from the Mises Institute. Jared wanted to understand Dread’s thinking and read along too. But the books were so dense that nothing he read made any sense. To him it appeared that the arguments made by the authors were just a series of justifications for doing things in the world without taking responsibility for how those actions might affect other people.

  All those books and all that research hadn’t brought Jared any closer to DPR.

  To make matters worse, Jared had heard from his counterparts at the Homeland Security office in Baltimore that a DEA agent, Carl Force, had managed to get close to the Dread Pirate Roberts, and Carl had been chatting with him undercover.

  Hearing this, Jared reluctantly asked the HSI Baltimore team to look through some of Carl’s chat logs to see if he could find more patterns in DPR’s language.

  When an e-mail arrived containing some of the logs, Jared was shocked at what the DEA agent was writing to DPR. Carl Force appeared to be offering more information than he should to the man he was supposed to be hunting, explaining how drug-smuggling routes worked and how to buy and sell heroin in bulk. It was one thing to curry favor with a perp whom you were trying to lure into public, but this felt like it was going several steps too far.

  As Jared sat at his desk in Chicago, staring at all the mail tubs on the floor, the Mises books on his desk, and the pictures of drugs that covered his walls, he felt so frustrated that he was being caught up in dead end after dead end. Jared needed a break in his case. Something, anything, just a little sign that he was on the right track.

  Chapter 37

  A PIRATE IN DOMINICA

  Welcome aboard, and thanks for flying with us.” The voice crackled over the intercom as the plane slowly edged along the tarmac of San Francisco International Airport. “Just in case, a life vest is located under your seat.” Ah, yes. The ominous what-to-do-in-case-of-an-emergency warning. A cautionary tale that served as the perfect allegory for Ross, who sat in the middle of the plane, nervously thinking about the last two hours and the next two weeks.

  Ross had expected an easy morning with some last-minute packing for his trip. But instead DPR had woken up to the discovery that the Silk Road was under attack by hackers who had brought the servers to a halt. To fend off the attack, Ross had been frantically working with Smedley, his lieutenant programmer, all morning.

  “I think we should install that waffle so we can see the results from mod-sec,” Smedley wrote as he tried to figure out what was happening. “Everything with a .txt extension can go into /etc/modsecurity/.”

  “Let me think,” DPR replied, frantic as the clock ticked down to his flight.

  “Disable everything.”

  “OK. We’ll need mysql, yea?”

  The morning had gone on like this for a couple of hours, and then Ross had no choice but to set off for his trip, leaving Smedley responsible for fending off the hackers.

  For Ross that was all irrelevant now. Poor DPR would not be able to log on to the Silk Road for at least six hours, until his next layover. He’d just need to trust that Smedley and his team of employees, whom he was paying between $900 and $1,500 a week for their services, had it under control. Sleep. That’s what he would do. He would need it when he landed. As th
e plane leveled off at 35,000 feet, Ross leaned back in his seat and closed his eyes.

  While he could have easily afforded to buy a Learjet (or two) and fly private, he had instead chosen to lie low and travel commercial. As a result, the travel alone for his trip was going to last almost two days and take him more than four thousand miles away from San Francisco. First he had to stop in Atlanta, Georgia, then catch a connection to San Juan, Puerto Rico. The following day, groggy and tired, he would take a small prop plane over a dozen tropical islands until he arrived in the Commonwealth of Dominica—smack in the middle of the Caribbean.

  This wasn’t a vacation. It was his trapdoor—his out. The final touch of an escape plan that had been in the works since he’d begun his security overhaul months earlier. A what-to-do-in-case-of-an-emergency scheme. After months of research and seeking the advice of Variety Jones, it turned out the Commonwealth of Dominica, where citizenship can be picked up for an “investment” of around $75,000, would serve as the perfect place for Ross to hide the Dread Pirate Roberts from the Feebs. It was also the ideal spot for Ross to stash his millions of tax-free dollars without Uncle Sam asking where all that money came from.

  The entire trip to Dominica was an exhausting slog. Ross would deboard a plane and find a private corner in the airport to open his laptop so that DPR could log on to the Silk Road and wage war against attackers before rushing off to the next flight. This went on again and again until Ross finally landed in the tropics.

  He stepped off the plane to see a tiny airport with a blue roof surrounded by tentacle-like palm trees. The taxi from the airport took almost an hour to get to the Fort Young Hotel on Victoria Street, where Ross was staying.

  When he arrived, he checked in, logged on to the site, and was immediately relieved to discover that Smedley had managed to squelch the assault against the Silk Road. Everything was back to normal—for now.

  Ross closed his laptop, crawled under the soft white sheets on his bed, and slept for fourteen long hours.

  When he woke up, sounds from the Caribbean were waiting outside his window. Birds—seagulls, pelicans, and colorful parrots—talked among themselves as the sound of the water washing over the rocks below trickled into the hotel. He walked out onto his balcony and looked off to the right, where the cruise ship dock sat empty. To his left he could see Champagne Beach and the top of Pointe Michel. It should have been the perfect morning in paradise, but when DPR went online, he found himself back in a living hell. While Ross had slept, the attackers had returned with a vengeance, and the Silk Road was completely incapacitated. A hacker who went by the moniker “JE” had e-mailed DPR and demanded a $10,000 Bitcoin bounty to stop the assault. DPR messaged his consigliere, Variety Jones, and asked what to do. “Pay,” VJ counseled.

  After all, $10,000 was nothing to DPR these days. Considering the Silk Road was now, on average, facilitating a quarter million dollars in sales each day, an hour of the attack was costing DPR more than the hacker’s measly ransom fee. (The $10,000 fee soon turned into a demand for a $25,000 payoff.) Reluctantly he sent the money.

  “Had to swallow my pride there,” DPR wrote to Jones after transferring the Bitcoins to the aggressor. But the site was back alive—again, just for now. Before the pummeling resumed, there was a lot of work to do to plug holes in the ship. VJ said that he would work with Smedley to get everything back in order and prepare for new assaults. “Take some time to meditate,” Variety Jones told DPR. “Get centered ‘n shit.”

  Ross was grateful that the relationship between the two men was now back at its peak, and they had started offering affectionate quips to each other once again, especially when they signed off the site at night. “Love ya :)” Dread would write to VJ, who replied, “Dude, you know I love ya’ too, eh.” At other times they would end the day with “smooches ‘n shit” and a “smoochie boochie” back.

  So when Variety Jones told Dread to go and meditate, that’s exactly what Ross did. He closed his laptop and set off through the hotel in search of a Jacuzzi. The resort was a stunning three-hundred-year-old inn that sat along the edge of the island. On the roof there was an infinity pool, and next to it a steaming hot tub. Ross slipped into the frothy water, his body feeling lighter under the weight of two worlds sitting on his shoulders. As he peered at the splendid Caribbean Sea, he took a deep breath and calmness enveloped his mind.

  These types of chaotic issues, like hackers and ransoms, didn’t bother Ross for long. In many respects he had started to enjoy them.

  “How lucky are we to get these problems,” he had written to VJ. “I always wanted big problems on my plate; never knew if I’d get there.” And such problems, he explained, had Ross thinking about his legacy and what he would leave behind when he was gone.

  “Winning the drug war is gonna be easy,” Jones said.

  “I think that’s more or less a foregone conclusion,” Ross replied.

  DPR wasn’t the first pirate to visit Dominica. For hundreds of years it had been home to real raiders, the ones who hid their booty in the caves around the archipelago. Now pirates like Dread could hide their digital wealth in bank accounts around the islands without worrying about the U.S. government reaching in and grabbing any of it.

  “My top priority right now is getting a new citizenship,” Ross had told Variety Jones, who had in turn counseled, “Make sure your plan includes at least two backup locales.” While Ross was in Dominica, he had also started exploring other countries, including Italy, Monte Carlo, Andorra, Costa Rica, and even Thailand, as alternate places to live if he went on the lam.

  But disappearing came with its consequences. Ross worried about those closest to him and whether he could handle never seeing them again. “I grew up here,” he said to VJ about leaving the United States. “My family is here.” And more important, he admitted, one day he wanted to start his own family. “The worst part is that I have no one to talk about this stuff with,” Ross wrote. “It just bounces around in my head.”

  Jones knew that feeling better than anyone, and he counseled his friend as best, and as sternly, as he could. “Best advice I can give right now is plan on a few years without emotional attachments,” VJ wrote. “Ex’s can put you in jail for life.”

  “I’m not complaining about any of this,” Dread wrote back, noting that this was a “great fucking problem to have.”

  Over the following two weeks Ross tackled his objective methodically. The process of getting citizenship wasn’t as easy as dropping a bag of hundred-dollar bills, or a thumb drive of Bitcoins, on someone’s doorstep. Ross had to gather letters of recommendation from some longtime Texas friends, telling them that he was exploring a citizenship in Dominica because there were some interesting tax opportunities for non–U.S. citizens. Then there were official forms to fill out, documents to submit, background checks, and even a medical exam. All annoying but necessary officialdom Ross had to go through for the sake of DPR and his future should he have to follow his emergency plan.

  When he wasn’t dealing with his citizenship application, Ross made friends in Dominica. There was Lou, a midthirties, sinewy local island woman who showed him the coves and shantytowns and poured him lots of liquor–and–Coca-Cola drinks, a Dominican specialty. He spent time at the beach, kicking a soccer ball back and forth with Kema, another local. He swam in the Lagoon River at sunset, then spent the evening under a gazebo on Purple Turtle Beach, eating barbecue, plantains, and rice, partying late into the night as the sound of the waves trickled onto the shore in the distance. It really was paradise.

  When his new friends asked Ross what he was doing in the country, he simply replied, “I’m here on business.” Sadly for Ross, that wasn’t far from the truth.

  He was forced to spend more time than he would have liked on his trip dealing with the growing pains of the site. Ross had to oversee customer-support tickets that seemed endless, with people complaining about drugs not arriv
ing on time, the site being too slow, or harassment on the forums. There were more hackers to fend off with even larger ransoms, the Feds to hide from, and his employees to inspire. Fudge, this was hard work. But Ross’s bank account was brimming with his bounty. When things were difficult, all he had to do was look at the spreadsheet with those numbers, and those numbers would look back at him, the ultimate pep talk to keep going.

  Thankfully for DPR, during this particularly tumultuous moment there was relief in sight: Silk Road Movie Night!

  Inspired by the clubs he had joined back at Penn State, and as a remedy for his loneliness, Ross had started Movie Night on the Silk Road, as well as the Dread Pirate Roberts’s Book Club.

  For tonight’s film, DPR had instructed everyone on the site that on “Friday the 16th, at 8 pm EST,” they should simultaneously press “play” on the movie V for Vendetta (with a link to download the film). The movie, DPR told his shipmates, was about a country under occupation by a police state and a vigilante known only as V, a masked marauder who fights against the government.

  Sure enough, at 8:00 p.m. Eastern, people from all over the world, including those in America, Thailand, and Australia, pressed “play” on their laptops as the picture began. And on the island of Dominica, Ross sat in his hotel room watching the film, enamored by its message. It was as if some lines had been written by DPR himself. “People should not be afraid of their governments,” V says in the film. “Governments should be afraid of their people.”

  Over the following week, as DPR worked on the site, he was invigorated by the message in the film. But unlike V in the movie, Ross had a different goal in mind: he was making money, lots of it.

  If the Silk Road had been valued as a start-up in Silicon Valley, it would now easily have been one of those fabled unicorns, worth a billion dollars or more. Venture capitalists would have been salivating to meet with the site’s CEO and invest millions more in the company. While most start-ups are in the red for the first few years of their existence, the Silk Road had mushroomed to be worth more than the value of the entire country Ross was visiting right now, Dominica. But for now it wasn’t a company; it was an illegal entity. It didn’t have a CEO; it had a leader who was a pirate. A pirate who at this moment was packing his bags at the Fort Young Hotel, preparing to leave paradise.