American Kingpin

by Nick Bilton

  “Give me a chance to chat with him,” Jared said.

  Tarbell typed an e-mail to the group, his palms sweaty. “Has NOT signed in yet,” he wrote, and then noted that the undercover agent on Silk Road (Jared) would need to lure the Dread Pirate Roberts into the site’s marketplace, ensuring he was caught with digital drugs and virtual money in his hand. If they didn’t get him with his laptop open and logged in to the site, and Ross managed to close the lid or press a key that encrypted the hard drive, the case could go poof! Finally Tarbell reminded everyone that when he gave the go-ahead, “PULL the laptop away, then get arrest.”

  When Jared saw “dread” appear in his chat window, the thought that popped into his head was Oh fuck! This is it. Any adrenaline that had been pumping through him a moment earlier went quiet as he focused on the task in front of him. Everything, he realized, came down to this very moment. An envoy of FBI agents was racing up the freeway; Tarbell stood nearby watching; and agents from the DEA, HSI, CBP, DOJ, IRS, ATF, and U.S. Attorney’s Office, as well as senators, governors, and even the president of the United States, were waiting to hear that this moment had happened without a hitch.

  Jared began typing into the Silk Road chat window on his computer. “Hey,” he wrote. But there was no reply. A minute went by and Jared typed “Hey” again. This time, though, he added a request for DPR: “Can you check out one of the flagged messages for me?”

  Jared knew that asking him this would prompt DPR to log in to the administrator section of the site, and if the man now sitting in the library a hundred feet away was really the Dread Pirate Roberts, that same man would be logged in to that section of the site if they grabbed his laptop. After what felt like an eternity, a ding finally sounded from Jared’s computer as a reply appeared on the screen.

  “Sure,” DPR wrote. “Let me log in.” And then he followed up with a strange question. “You did bitcoin exchange before you worked for me,” Dread wrote. “Right?”

  For some reason DPR was testing him. Jared’s mind started to swirl with worry. Did DPR know something was up? Jared scanned his mind trying to remember the right answer.

  3:13 p.m.

  A young Asian woman wandered through the library plucking books from the shelves. After a while she came around the corner of the stacks, standing in front of the science fiction and romance section, and pulled up a chair at the round beige table where Ross sat. His backpack rested next to him; his laptop glowed as he typed away. He peered over his computer screen at the young woman. She had a fair complexion and was perusing the pile of books in front of her. She seemed safe enough, so Ross looked back to his computer, his fingers methodically moving up and down on the keyboard as he typed.

  3:14 p.m.

  Jared thought, trying to remember what the woman from Texas had told him in August when he had taken over her account. Had she done Bitcoin exchange? Or had she not? He took a deep breath and took a chance, replying, “Yes, but just for a little bit.”

  “Not any more than that,” DPR replied, still fishing for an answer. A test indeed.

  “No,” Jared wrote back, “I stopped because of reporting requirements.”

  What he said must have worked, because Dread soon asked, “Ok, which post?” He was now definitively logged in to all three administrative areas of the Silk Road. Jared looked up at Tarbell and began swirling his finger in the air like a helicopter about to take flight. “Go, go, go,” he said swiftly. “Go!”

  Tarbell’s thumbs hammered down on his phone as he typed as fast as he could. “He is logged in,” he wrote, followed by “PULL LAPTOP—GO.” He scrambled across the street and into the library.

  Jared came running up behind Tarbell. It was pure adrenaline now. They both hurried up the library steps until Tarbell came to a swift standstill midstride and swung his arm out to stop Jared. “Let them do their thing,” Tarbell whispered.

  For ten seconds Jared and Tarbell didn’t say a word. They just stood there, frozen on the concrete steps of the library. And then they heard it. The yelling and commotion that had just erupted inside the quiet library on Diamond Street.

  Chapter 65

  ARRESTED

  3:15 p.m.

  One minute the library was silent; the next, an Asian woman yelled, “Fuck you!” at a man standing next to her.

  Everyone in the library looked up, startled by the outburst. The man who had just been told to go fuck himself raised his fist to seemingly punch the woman in the face. As his clenched hand went into the air, a startled Ross Ulbricht turned around in his chair to witness the commotion.

  And just in that moment, as Jared and Tarbell stood at the base of the stairs, the Asian woman with the fair complexion who had been seated at the table across from Ross reached over and gently slid his Samsung laptop away from him. Ross turned back, half comprehending what was going on as he tried to lunge for the laptop. Yet he couldn’t. Someone had grabbed his arms from behind.

  “FBI! FBI!” the couple who had just been yelling at each other now bellowed at Ross as they slammed him against the table. Brophy rushed over, slapping handcuffs around Ross’s wrists, and retrieved him. Thom, visibly shaken by the intensity of the moment, came to retrieve the laptop, which was still wide open and, thanks to Jared, also logged in to all three administrative areas of the Silk Road, including the “Mastermind” page, an area of the site that only the Dread Pirate Roberts and Ross Ulbricht could log in to.

  As Tarbell and Jared entered the second floor of the library, Brophy appeared, holding by the arm a young man who was now handcuffed and had a panicked look on his face.

  “This is going to be your new best friend,” Brophy said to Tarbell and Jared as he handed Ross Ulbricht over to them.

  Inside the library patrons started to yell at Brophy and the others. “What did that kid do?!” they hollered. “Leave him alone!” To them the young man now in handcuffs had been minding his own business, just using his laptop.

  Tarbell and Jared led Ross down the concrete steps, out into the street. Tarbell then turned Ross around, gently placed him up against a wall, and began patting him down. In Ross’s pockets there were only two $1 bills, some spare change, and a set of house keys.

  “I am Special Agent Chris Tarbell with the FBI,” he said as he spun a handcuffed Ross back around, placing his hand on Ross’s chest to ensure he wasn’t having a heart attack or any other emergency. “Do you have any medical conditions? Do you need any medical attention?”

  “No, I’m fine,” Ross said. The shock of the moment had already worn off and Ross was now nonchalant, as if this was just a small bump in the road. “What am I being charged with?” he asked, knowing full well that the cops could have grabbed him for any number of reasons. Maybe it was the fake IDs he had ordered or something innocuous related to the Silk Road.

  “We’ll go over that in the car,” Tarbell replied, “once we get you off the street.”

  FBI cars and vans from the local FBI squad now screeched in from all angles and directions onto Diamond Street, with almost thirty agents swarming in every direction. Tarbell walked Ross toward an undercover van that was stopped in the middle of the road as Jared walked back upstairs to check the laptop they had seized during the arrest.

  The library was quiet again as Jared made it to the seat next to Thom, who was taking photos for the arrest report. As Jared scanned the screen, he saw it. The other side of the chat that he had been engaged in with DPR a few minutes earlier. The computer was logged in, using Tor, on the Silk Road support page and on a dashboard called Mastermind, which displayed a bounty of millions and millions of dollars in Bitcoins. Off to the right there was a chat window, which was midway through a conversation with Cirrus—Jared’s undercover account—and there was the name of the man he had been chatting with: “Dread.” The computer was called “Frosty.”

  “Holy shit,” Jared said aloud.

  Dow
nstairs Tarbell helped Ross into the backseat of the undercover van. “You asked what you’re being charged with,” Tarbell said. A woman sat in the front seat wearing an FBI jacket, and behind her a child’s seat sat empty. Next to it Ross was now settling in with his hands cuffed behind his back. Tarbell then lifted up a piece of paper and held it in front of Ross’s face for him to read. As Ross looked at the page, he saw the words written across the top:

  UNITED STATES OF AMERICA

  -v.-

  ROSS WILLIAM ULBRICHT

  a/k/a “Dread Pirate Roberts,”

  a/k/a “DPR,”

  a/k/a “Silk Road.”

  Ross’s eyes narrowed as he looked at Tarbell and uttered four words. “I want a lawyer.”

  Chapter 66

  THE LAPTOP

  In the corner of a smoggy industrial park in South Korea, as the sun peeks through the morning dew, thousands of men and women wake up and move toward several enormous factories. They all wear the same uniform—a flamingo-pink jumpsuit and matching rose cap. The workers never pause, going day and night, trading out their positions like cogs being swapped out of a clock that is incapable of stopping. For hours upon hours, day after day, they will assemble computers for Samsung Electronics Limited.

  Thousands of times a minute a Samsung laptop is built by those workers. The LCD screen is connected to the chassis; the SSD hard drive encased in its aluminum housing; chips soldered to green circuit boards. Robotic arms ensure the hinges of the laptop open and close properly. Then these things that moments earlier were just scraps of metal and silicon and plastic come to life. The glowing computers are loaded with software, placed into boxes, and wheeled away through the building, entering the vast logistical arteries of the worldwide shipping systems.

  In April 2012 one of those Samsung laptops was purchased online for $1,149. It traveled 6,989 miles away from that factory in Korea to a quaint home in the suburbs of Austin, Texas. No one but Ross Ulbricht and the Dread Pirate Roberts ever touched that Samsung 700Z, that is, until the afternoon of October 1, 2013. While Ross was whisked away to the nearby jail with Tarbell, the silver Samsung laptop was carefully carried by Thom Kiernan of the FBI down the stairs of the library, out onto the street, and into the back of Brophy’s unmarked police car.

  Thom walked carefully with the machine, as if he were transporting an egg resting in the bowl of a spoon. There, with Jared in the backseat next to him, Thom nervously moved his finger back and forth along the mouse to ensure the laptop stayed alive as they made their way a few blocks to Ross Ulbricht’s house, where a mobile computer forensics lab waited outside.

  The forensics truck was a large white beast the length of a small yacht. There were no windows in the back. Inside, a long gray desk stretched from the front of the van to the rear, with computer equipment everywhere. Screens flashed amid a snake pit of wires, and a long row of power outlets stood at the ready, with a computer forensics expert from the local FBI office waiting to receive the laptop.

  Thom and the other agent started checking the computer for booby traps, probing to ensure that the machine wouldn’t die if they plugged it into an external drive that they would use to siphon out all of the files. It was then that Thom saw a “scripts” folder. In it there was code that Ross had written to protect the computer in case of this very scenario.

  A few feet away FBI agents swarmed Ross’s house, looking for evidence and clues that would tie him to the Silk Road. In the garbage can they found a handwritten note that was scribbled on a piece of crumpled paper, outlining a new file system he was building for the site. On Ross’s bedside table two thumb drives sat, though the Feds didn’t know yet what those drives contained.

  Over the next ten hours the Samsung computer was copied half a dozen different ways. Backups were made of backups. Agents came and went. They ate McDonald’s as they worked. The streetlights flickered on and the forensics van was moved to an FBI safe house nearby. When Tarbell arrived after dropping Ross off at central booking, Thom and his forensics colleague were trying to go deeper and deeper into the computer, with the hope that they could pluck Ross’s passwords out of the laptop’s memory, possibly to enter the other side of the laptop. The Ross Ulbricht side. But at around 2:00 a.m., as they tried to break into the other side of the machine, it died.

  They had the backups of the computer, but it would be days before they found out exactly what kind of evidence they had retrieved.

  A couple of miles away, in a stone jailhouse on Seventh Street in San Francisco, Ross sat staring at a concrete wall, frightened by where he found himself but unfazed by how long he might be in jail. He had played through this scenario a thousand times before. Sure, they had caught him with his fingers on the laptop while he was logged in to the Silk Road as DPR. But that didn’t mean that he was the DPR who ran the Silk Road. There could be more than one Dread Pirate Roberts, like the old tale in The Princess Bride.

  Ross was sure that they would never be able to figure out his passwords on the computer, either. All the most important files had been encrypted and locked under his secure code word, “purpleorangebeach.” No one, not even the FBI, would be able to figure that out. The most they could prove, he was sure, was that he was logged in to the site when they arrested him. And that didn’t mean anything. In a worst-case scenario he knew he could admit that, sure, he had once been involved in the Silk Road, but he had handed the site off to someone else years ago. If the FBI asked whom Ross had given the site away to, he could simply say, “I don’t know who it was. All I know is that they called themselves the Dread Pirate Roberts.”

  Chapter 67

  ROSS LOCKED UP

  For the first two weeks after his arrest, inmate number ULW981 was locked up in solitary confinement at a jail in Oakland, California. His street clothes were taken away, exchanged for a red prison jumpsuit with ALAMEDA COUNTY JAIL written across the back. His shoes were swapped out for a pair of socks and flip-flops. His wrists were shackled to a chain around his waist. He was allowed outside for one hour a day as he waited to be transported to New York City, where he would hear the charges against him and stand trial.

  The news of his arrest was like an atom splitting on the Internet. Thousands of blogs, newspapers, and TV outlets covered the story of the Boy Scout who had secretly been running a Web site that, the FBI alleged, had trafficked $1.2 billion in drugs, weapons, and poisons, in just a couple of years.

  For those who knew Ross, the story, and his arrest, just didn’t add up. His friends and family believed that it was one giant mistake.

  When a reporter called his best friend, René, whom Ross had stayed with on Hickory Street in San Francisco, asking what he knew about Ross’s involvement in the Silk Road, René was so flabbergasted and confused that he said, “I don’t know how they messed it up and I don’t know how they got Ross wrapped into this, but I’m sure it’s not him.” When Ross’s family found out, they felt the same way. There was just no way that Ross could be involved in such a site. Cousins, aunts and uncles, and his siblings, were sure that he had been framed. That the truth would set him free. On Facebook elementary-school chums, high school buddies, and old neighbors shared links in disbelief, shocked by what they read. There’s no way. Not in a million years. Not Ross.

  In San Francisco one of the men whom Ross had lived with on Fifteenth Avenue was walking to work and stopped to pick up a copy of the San Francisco Examiner. On the front page of the paper, above the fold, there was a picture of Ross smiling next to a screenshot of the Silk Road. The roommate snapped a photo of the front page with his smartphone and then sent it to the other renter in the Fifteenth Avenue apartment. “Funny,” he wrote in the text message. “Looks kinda like our subletter,” Josh.

  “Not looks like,” the other roommate replied. “Is.”

  “Holy shit . . .”

  And then there was Julia, who had planned to video chat with Ross th
e night he was arrested. She had stripped down to her sexy lingerie and logged on to Skype, hoping to see a handsome Ross staring back at her through his laptop camera. But he never showed up. She rang and rang, trying to reach him, but no one answered. She was completely unaware that at that very moment, the man she hoped to flirt with through a tiny little camera on her computer was sitting in handcuffs in a jail cell, and that his laptop was being probed in an FBI forensic truck by two federal agents. Eventually she gave up trying to call him that evening, assuming that Ross had forgotten about their online assignation, and she went to bed alone.

  The next morning a client came into her office, and as they sat going through photos, Julia’s cell phone rang, interrupting the meeting. It was a friend from Austin who simply uttered the words “Google Ross Ulbricht.”

  “Huh?” Julia queried.

  “Just do it,” the friend demanded. “Google Ross Ulbricht’s name.”

  Julia turned to her computer, typed in a name she had written ten thousand times before, and waited for the results to load on her screen. When she saw the news she almost fainted. Shock took over her body as she fell on the floor and began wailing.

  • • •

  Two weeks later Ross boarded a flight on Con Air (a nickname given to the prison airline that transports inmates) to New York City. When he landed, after an arduous zigzag across the country, picking up and dropping off other prisoners, Ross was placed into the general population in a Brooklyn jail, where he would live until his trial began.

  His devastated parents flew up from Austin to see him, friends made the pilgrimage to show their support, and Ross met his new lawyer, Joshua Dratel, a stalwart attorney who was known for defending some of the most notorious criminals on American soil, including two men who were involved with the U.S. embassy bombings in Kenya and Tanzania that killed 224 people. Ross had chosen Dratel because he saw him as a lawyer who subscribed to the philosophy that someone’s beliefs shouldn’t be a crime and that the system should offer everyone—even alleged terrorists—a fair trial.