American Kingpin

by Nick Bilton

  “Holy shit!” Serrin blurted aloud. “It’s around the fucking corner from Momi Toby’s café, where we found the IP address.”

  Gary leaned back in his chair as Serrin leaned forward in his.

  To Serrin it made no sense that a kid with no programming background, whose Facebook photos were mostly moments of him camping, kite-boarding with suburban friends, and hugging his mother, was responsible for creating what authorities now believed was a multibillion-dollar drug empire. And what made even less sense was that this kid had ordered the cold-blooded murders of almost half a dozen people. Nope. It simply didn’t add up. But it also didn’t add up that this kid lived a block away from Momi Toby’s café, that he was the first person on the Internet who had ever written about the Silk Road, and that he had been caught buying nine fake IDs.

  “I’m going to send out an e-mail to Jared and Tarbell,” Serrin said. “I want to get us all on a conference call.”

  • • •

  The office in the Dirksen Federal Building, where Jared sat, was completely sparse. There were no computers or books in the room, just a solid oak desk and a phone that Jared was now reaching for.

  He looked at the e-mail he had received from Serrin a few minutes earlier and began dialing the number for the conference call. As the phone rang, Jared sat back in his chair, slouching exhaustedly as he blankly stared out the window at Chicago’s skyline.

  • • •

  Tarbell walked into his house in New York, greeted his wife, Sabrina, and the kids, and said he had to hop on a quick conference call. He walked into his bedroom and began his evening ritual, kicking off his dress shoes and suit and replacing them with a stained pair of Adidas shorts and a T-shirt. He then belly flopped onto the bed with a thud. He was so tired he could have closed his eyes at that moment and slept for a month. But instead he let out a deep, exhausted sigh and reached for the devices in his bag.

  Like a casino dealer fanning out a deck of cards, Tarbell placed his laptop, iPad, and phone out in front of him. He then dialed the conference-call number from Serrin’s e-mail and stared blankly at his iPad, which lay in between the two other devices, displaying the map Serrin had sent out an hour earlier.

  • • •

  “Gary.”

  “Serrin.”

  “Tarbell.”

  “Jared.”

  “We all here?”

  “Yes.”

  Serrin began speaking, giving Jared and Tarbell a recap of the conversation he had wrapped up with Gary a few minutes earlier. He then asked Gary to tell them what he had found.

  Gary began talking with a sense of urgency in his voice. He explained about the Google search and how the very first reference to the Silk Road online originated in a forum post on the Shroomery Web site in late January 2011, from a person with the username Altoid.

  Tarbell and Jared were somewhat nonchalant about the evidence Gary was presenting. Maybe Altoid was just an early user on the site. And coincidences were easy to find in a case this large. God knew there had been dozens of coincidences with other people. Agencies had ruminated over the leader of the Silk Road being the CEO of a Bitcoin exchange, a Google engineer, or even a professor at a U.S. university. Others had believed it was an inner-city drug dealer or possibly the Mexican cartels now working with programmers. And some had surmised that it was Russian hackers or Chinese cybercriminals. Yet here was Gary Alford, insinuating that the ruthless, deriding, and wealthy Dread Pirate Roberts was a twenty-nine-year-old kid from Austin, Texas, who had no programming background and who was living in a $1,200-a-month apartment in San Francisco.

  Jared wasn’t sold. Tarbell wasn’t, either. And Serrin knew that if they weren’t, he certainly wasn’t. Jared, after all, had spent the most time with DPR, working for him for months undercover and chatting with him extensively online. Plus, Jared had an entire office full of fake IDs and people admitting they had gotten them from the Silk Road, and they certainly weren’t DPR.

  But Gary continued to talk.

  “And then I found a question posted on Stack Overflow, where a user by the name of Ross Ulbricht had asked about coding help with Tor. You know?” Gary said. “And then, a minute after he had posted the question on Stack Overflow, he went in and changed his username from Ross Ulbricht to Frosty, and then—”

  “What did you say?” Tarbell interrupted, sitting up in his bed.

  Gary was caught off guard by the question but answered anyway. “Stack Overflow. It’s a site where you can post programming questions—”

  “No, not that,” Tarbell said, his tone coming across as aggressive. “What did you say after that?”

  Gary explained that Ross Ulbricht had signed up for an account on Stack Overflow with his real e-mail as his username, but a minute after asking a question on the site, he had changed the username to Frosty.

  Jared and Serrin listened silently, unsure of what this all meant.

  “Frosty?” Tarbell said, now sounding amped. “Are you sure?” He then impatiently spelled out each letter: “F-R-O-S-T-Y—as in ‘frosty’?”

  “Yes! Frosty!” Gary replied, growing annoyed that Tarbell was being so rude. “And he later changed his e-mail address to frosty@frosty.com. What’s the deal? Why do you keep asking that?”

  “Because,” Chris said, taking a deep breath, “when we got the server from Iceland”—he took another breath—“we saw that the server and the computer that belonged to the Dread Pirate Roberts were both called ‘Frosty.’”

  The phone line was dead silent, just a hush of air as the four men sat contemplating what they had all just heard.

  Finally the speechlessness broke. “Well,” Serrin said. “That’s interesting.”

  As this settled in, Jared looked up “Ross Ulbricht” online, and came across his YouTube page, where, amid a dozen videos about libertarianism, was the title that Ross had given his YouTube account: “OhYeaRoss.” There it was, the word that DPR used all the time in his chats with Cirrus: “yea.”

  No h at the end, just “yea.”

  Chapter 61

  THE GOOD-BYE PARTY

  The beach was eerily dark and quiet as the white pickup truck pulled into the parking lot. Specks of yellow from the streetlights hung in the air, trying desperately to bleed through the San Francisco fog. Waves crashed rhythmically into the sand. As Ross stepped out of the truck, he pulled his thick black jacket tight to stay warm. The air was salty and wet.

  He looked out at the dark horizon, and while there wasn’t much to see, it was the beach, and it was beautiful.

  If only time could have stood still in that instant, these next few hours could have lasted forever. But that wasn’t possible. The laws of time, like gravity, are nonnegotiable. And time for Ross was running out.

  But still, the San Francisco night was willing to offer up something special for Ross as a last hurrah. A night of revelry. Out of the darkness behind him, a friend yelled, “Let’s build a bonfire!”

  They began unloading the pickup truck, which Ross had helped fill two beds high with dead logs and scraps of wood, all scavenged from Glen Canyon Park, a few blocks from Ross’s home.

  His new roommate, Alex, was there. René and Selena too. Other friends were in town from Austin, a dozen people in all. The fire was lit and soon began to roar. Champagne was popped open. Beers too. A joint was passed around. Ross grabbed his djembe drum, his hands slapping the goblet-shaped leather as loud thuds hit the air.

  The sounds were reminiscent of his days in college when he had joined the NOMMO group at Penn State. If it hadn’t been for that drum circle, he might never have met Julia in a nondescript basement at school. If it hadn’t been for the libertarian club he had joined, he might never have become who he was today.

  He had sailed a million miles since then and helped a million people along the way. The Ross of back then had been an ideali
stic lost soul; this Ross had changed the world. The other Ross had been worth a few hundred dollars; this one was valued at a few hundred million. That guy had read the works of influential libertarians like Rothbard, Mises, and Block; and yet now Ross Ulbricht was a ghostwriter for the most influential libertarian of them all: the Dread Pirate Roberts.

  Or maybe it was Ross alone penning those words. In many respects the two of them were now indistinguishable. Sweet Ross was still in there somewhere. He had recently seen a piece of trash caught in a tree in the park and had climbed the branches, higher and higher, to rid the park of the dangerous plastic bag. But his kindness had come with consequences. “I have poison oak rash from head to toe,” he had e-mailed Julia a few days later. “I wish you were here to comfort me :(.”

  Still, the ointment that could fix the pain would come soon enough, when Ross would be able to see Julia again. He had booked a flight to Austin, planning to leave in a couple of weeks. He was done with San Francisco. What choice did he have? The city knew too much. He would go to Austin first, find another hiding place. Probably somewhere far, far away, where he could see his vision through. Maybe it would all be a new beginning.

  The site was making more money than he knew what to do with. He had tens of millions of dollars on thumb drives scattered around his apartment. The problems, though abounding, had simply become daily work obstacles for Ross. When he wrote in his diary that he had loaned a dealer half a million dollars, or had Variety Jones deploy one of his soldiers to deal with another problem, or paid hackers or informants $100,000 apiece, it was just a day in the office for Ross. Murders, extortion, reprisals, and attacks had all just become the job. Sure, it was stressful at times, but in Ross’s alternate universe he was king.

  On the beach, as the fire roared, a massive fireworks display began exploding in the distance like a magical, colorful rain. Boom! Boom! Boom! The thuds of the drum mixed with the sound of fireworks bursting overhead, their burning embers sprinkling into the ocean.

  At around midnight two new visitors joined the group, though not the kind that Ross wanted to see: two San Francisco police officers walked up, inquiring into what was going on. But they weren’t here for him. They politely said it was time to put out the fire; the beach was closing. One minute red sparks shot violently into the sky, the next sand was being kicked over the embers as darkness returned to the beach.

  The troupe of friends gathered their things and walked back toward the parking lot, in the direction of the white pickup truck.

  The party, it seemed, was over.

  As Ross slipped his black jacket back on and looked out into the darkness, he had no idea that a team of undercover FBI agents were looking back at him, and that for the past two weeks they had been watching his every move.

  PART V

  Chapter 62

  THE PINK SUNSET

  Pink.

  That’s what it was. Vast and pink and endless.

  A magnificently surreal pink sunset that covered San Francisco from above. Jared couldn’t take his eyes off it. He gazed down from the window of the plane, and for a moment he was reminded of just how insignificant we can all feel sometimes, plodding through our lives, working our menial jobs, and thinking we don’t really matter—and yet from a different viewpoint we get to see that we all do.

  As the plane banked to the left, preparing to land, Jared pulled out his smartphone and snapped a picture to preserve the moment. A memory to capture the pink sky before he, Jared Der-Yeghiayan, helped capture the Dread Pirate Roberts. That was, if they were actually able to catch him. According to Tarbell, there was a problem, and Jared had to get to the hotel as soon as possible to discuss the issue with the FBI team on the ground.

  At almost the second the United Airlines flight’s wheels screeched onto the tarmac of the airport, Jared reached for his laptop and a Wi-Fi hub and logged on to the Silk Road. He hadn’t wanted to take a chance that DPR would try to contact Cirrus while he was in the sky, so Jared had an HSI agent in Chicago pretending to be Jared, who was in turn pretending to be a woman from Texas, while Jared flew into San Francisco. It was complicated, but when he landed, he saw that the handoff had, thankfully, gone unnoticed.

  The undercover account had proved more useful than Jared could ever have imagined to ensure that Ross Ulbricht really was DPR. It was one thing to have a suspect; it was something entirely different to gather enough evidence to convict him.

  Shortly after the phone call among Gary, Tarbell, Jared, and Serrin, the FBI had assigned a team of undercover agents to trail Ross. For two weeks they followed Ross as he went for a walk in the park, peered over his shoulder as he was on a date with a girl at a restaurant in the Mission, or while he was out for a drink with his friends. But it was when he wasn’t doing those things that Jared’s account had become invaluable.

  Whenever Jared saw the Dread Pirate Roberts log on to the Silk Road, he would let the undercover FBI team on the ground know, and they would confirm that at that very moment, Ross had opened his laptop too. Then, when DPR logged off the site, the undercovers would confirm that Ross had closed his laptop. So ensuring Jared was online all the time was imperative to the investigation.

  He got off the plane at SFO, his laptop in one hand, his bags in the other, and he set off to the hotel, utterly exhausted. He hadn’t slept more than a couple of hours at a time since the phone call three weeks earlier, and there was no sign that was going to let up anytime soon.

  Jared checked into his room at the hotel and made plans with Tarbell to meet at the steak restaurant in the lobby to go over the logistics of the coming days. Tarbell introduced Jared to a large ex-marine called Brophy, who was a “badass” special agent with the New York FBI and had come out to San Francisco to assist with the actual arrest. Thom, the computer scientist from the New York office, whom Jared had met before in New York City, was there too. Thom had one job, which was to keep Ross’s computer powered on and logged in if they captured him with his hands on the keyboard. But there was a problem with that part of the operation. As they ordered beers, Tarbell explained that the local FBI team in San Francisco was going to be responsible for the arrest, as this was in their jurisdiction (this was standard FBI procedure) and that the local agents wanted to go into Ross Ulbricht’s house with a SWAT team.

  “Oh, fuck.”

  “Yeah.”

  Tarbell had made this mistake before during his LulzSec bust, and he knew that they could arrest Ross Ulbricht ten thousand times over, but unless they caught him with his hands on his laptop, they might not be able to prove that they had captured the Dread Pirate Roberts. All it would take was a glimpse of a Fed or the sound of a footstep, and Ross could touch his keyboard, encrypting the evidence on it. Sure, they could tie him to the site with the log-ins from Momi Toby’s café and the surveillance the Feds and Jared were building together. But a good lawyer could say that was all coincidence.

  “What are we going to do?” Jared asked.

  “I’m going down to the local FBI office tomorrow to try to talk them out of going in with SWAT,” Tarbell replied.

  “You think it’ll work?”

  “It has to.”

  But Tarbell knew it would be a tough sell. As the FBI briefing reports noted, the Dread Pirate Roberts was dangerous. From what Tarbell and his crew had pulled from the servers, it appeared that DPR had had people murdered—several people—and that he had ties to the Hells Angels and other hit men. For all they knew, DPR was going to go down with a fight. Maybe a fight to the death. And the higher-ups at the Bureau weren’t going to risk losing a single FBI agent if that proved to be true. To top it off, the director of the FBI had briefed the White House about the sting, which meant the president of the United States would know if the operation was a success.

  Brophy, the gruff agent, interrupted. “I should’ve grabbed him today.”

  “Whaddaya mean?” Jared aske
d.

  Earlier that day, Brophy explained, the undercover team had tracked Ross to a nearby coffee shop, where he sat on his computer for a couple of hours. Brophy walked into the café and sat right next to him, and while Brophy was big enough that he could have taken him right there and then, there was a chance that Ross wasn’t logged in to the Silk Road, and they would have captured him simply checking his e-mail. If Jared had not been on that plane, they might have been able to check if DPR was logged in to the site and arrested him if he was, but they couldn’t take that chance, so Brophy let him go.

  “No shit?!”

  “Yep.”

  “Well,” Jared sighed as he observed his laptop, “he’s logged in now.” He then asked, “So what are we going to do?”

  “I’m not sure. Let’s see what the ASAC says tomorrow,” Tarbell said, referring to the local assistant special agent in charge. Tarbell swallowed a gulp of his beer the way someone downs a shucked oyster, and as he did, he was reminded of something he had forgotten to share with Jared. “You wouldn’t believe who fucking called me before I flew out!”

  “Who?” Jared queried as he took a bite of his burger.

  “Carl Force! And he was being adamant that he wanted to see the server; he was almost defiant about it, acting like a real dick. I told him if he wanted to see it he had to go through my ASAC.”

  “The Baltimore guys are so fucking unprofessional,” Jared said as he shook his head. “I swear something’s up with Carl; something doesn’t feel right.”

  The agents spent the next forty-five minutes telling stories about just how unprofessional Carl and the team in Baltimore had acted toward them during the investigation, with Brophy and Thom listening in shock. Though none of them had any idea yet just how unprofessional.