American Kingpin

by Nick Bilton

  So late that evening, as he lay on his red bed, his head on his red pillow, Gary had an idea.

  He wondered about the first person to ever write about the Silk Road on the Internet. As far as everyone knew, it was Adrian Chen, the blogger for Gawker who had published the notorious first story on the Silk Road. Maybe, Gary thought, Adrian Chen was really the Dread Pirate Roberts.

  If so, then maybe Adrian Chen would have written about the Silk Road somewhere else before he wrote about it on Gawker.

  So Gary went to Google on his laptop and read the Gawker article again, three times. On his last pass he saw something interesting in a link that he hadn’t seen before: that instead of“.com,” the Silk Road’s URL was followed by “.onion,” which was the domain used on the Tor Web browser.

  With that, Gary went back to Google, typed “Silk Road.onion” into the search box, and then filtered by date, saying he wanted to see only results from before June 1, 2011, the day the Gawker article was published. This time only a handful of blue links appeared. Click. Click. Click again. And out of nowhere he saw a post on a forum called the Shroomery that had been posted at exactly 4:20 p.m. on Thursday, January 27, 2011—the same week the Silk Road had allegedly opened for business. He clicked the link and began reading.

  “I came across this website called Silk Road,” someone had written on the Shroomery back in 2011. He continued to skim the Shroomery Web site, which explained how to grow magic mushrooms, until he noticed that the author of the comment about the Silk Road called himself Altoid. Gary sat up in bed.

  “Where are you going?” Gary’s wife asked, half asleep, as he stood up.

  “Downstairs,” he whispered. The blue glow of his laptop left the room as he walked across the hall. Paulie jumped down and scampered behind him.

  He sat on the couch in the living room and continued to look further. He went to Google again, this time typing in “Silk Road.onion” and “Altoid,” and a couple more blue links appeared. Click. Click. Click. And there was another post on a separate forum that talked about the idea of creating a “Heroin Store” that would allow people to buy “H” on the Internet using Tor and Bitcoin. And as on the other site, there was a post written by Altoid.

  “What an awesome thread! You guys have a ton of great ideas. Has anyone seen Silk Road yet?” Altoid had written around the same time, in January 2011. “It’s kind of like an anonymous amazon.com.”

  Over the coming days Gary contacted these forums and, using his government credentials, requested the names and e-mail addresses that were associated with the “Altoid” accounts. It appeared that they had been registered to someone with the e-mail address “frosty@frosty.com,” which wasn’t a real e-mail account and went nowhere. But as Gary dug further, he discovered that the Altoid username had another e-mail address associated with it that had since been deleted but still existed in the forum’s database.

  The account, he discovered, belonged to a “RossUlbricht@gmail.com.”

  Another search showed that Ross Ulbricht was a white male from the suburbs of Texas in his late twenties. But there was something missing from the profile of this new suspect: Ross Ulbricht had no computer science background.

  Of course, being the first person to ever post about the Silk Road online by no means meant that this was the man who had created the Amazon of drugs. For all Gary knew, dozens or even hundreds of people might have already been discussing the site in private chats, or on unsearchable areas of the Internet, before “Altoid” wrote about it on those forums. But it was enough to add Ross Ulbricht’s name to a handful of other suspects Gary had been collecting, all people who might be, in some way or another, involved with the Silk Road.

  While he didn’t know it at the time, Gary had just discovered the equivalent of a parking ticket on the Son of Sam’s car. Except this one was on an obscure post left on a forum on the Internet.

  Chapter 51

  TARBELL FINDS A MISTAKE

  Chris Tarbell bolted out of the U.S. Attorney’s Office at 1 Saint Andrews Plaza in New York. He was walking at a brisk pace toward the FBI headquarters across the street as he reached into his pocket and grasped a tiny gray thumb drive that could change the world—at least, Chris Tarbell’s world.

  He could barely contain the excitement at the reality that the thumb drive he held possibly contained the servers for the Silk Road. The drive had arrived in the mail that morning, shipped from authorities in Iceland. If the server it contained was not encrypted, it could possibly lead the FBI to the Dread Pirate Roberts.

  When the FBI had opened the official investigation into the Silk Road a couple of months earlier, Tarbell and his small team of federal agents were already a thousand steps ahead of every other government group working the case. The cybercrime agents had, after all, spent years hunting for and arresting people on the Dark Web, taking down hackers, pedophiles, identity thieves, and even terrorists, many of whom had adopted these technologies as silent weapons.

  The FBI agents also knew that, more often than not, the malevolent people they hunted made mistakes. Sometimes small and seemingly innocuous blunders, but mistakes nonetheless. Often all the agents needed to do to crack open a case was to find one of these.

  Which was what Tarbell had recently done.

  Given his background in computer forensics, Tarbell could scour technical forums online that discussed the code that held the Silk Road together and actually understand what people were saying. Soon after opening his investigation, Tarbell noticed something that other experienced programmers had seen online: that a recent update to the Silk Road server had left a small but potentially fateful mistake open on the site’s log-in page. The error appeared to leak the server’s IP address, a series of numbers that was akin to a home address but, rather than pointing at a house, pointed at a server, even a hidden one on the Dark Web.

  Upon investigation, it turned out the mistake was a real clue, and after a few hours running software that took advantage of the error, Tarbell was able to pinpoint the IP address that housed the server that stored the Silk Road, which was, it turned out, in Iceland. (Hours after he found the error, the Dread Pirate Roberts saw it too and patched the hole.) It was a huge break in the case, but it was unclear what, if anything, was on that machine. In one scenario the server could tell the FBI the who, what, when, and where about the people who ran the site. But if the server was encrypted, which it likely was, or even deleted by the time they reached it, the clue could amount to absolutely nothing.

  It had taken several weeks, a quick trip overseas, some legal wrangling, and a few beers with some Icelandic cops to get Iceland to hand over all of the information on the server. And then in mid-June a copy had arrived by mail at the U.S. Attorney’s Office on a gray thumb drive (likely swimming alongside some drugs that had been purchased on the Silk Road).

  Tarbell, now holding that drive in his hand, swept past the security guards at the FBI building. He clicked his key card and charged toward the twenty-third floor, looking for Thom Kiernan, the computer scientist he worked with in the cybercrime group.

  “I got it,” Tarbell said gleefully when he found Thom in lab 1A.

  The computer station in the lab was a long bench with monitors, keyboards, and hard drives in every direction. The two men pulled up chairs in front of one of the machines as Tarbell handed Thom the drive, watching with rapt anticipation as he placed it in the computer. Thom’s fingers started rapidly dancing on the keyboard, opening the folders and delving into its content. The two men were anxiously excited at the possibility of what it might hold. And then Thom’s expression crumpled. He turned to Tarbell despondently and said the last two words on earth that either of them wanted to hear: “It’s encrypted.”

  On the screen in front of them was an endless string of random characters, numbers, and letters that looked like complete gobbledygook. Thousands of lines of unintelligible garbage.
<
br />   Tarbell was deflated as he picked up the phone and called Serrin Turner at the U.S. Attorney’s Office, the man who had just handed him the drive, leaving a voice mail that said to “call me back as soon as possible; there’s a big problem.”

  “Fuck!” Tarbell blurted out as he slammed the phone down. “It’s game over.”

  After a few pointless attempts at unlocking the folders (which was akin to trying to break into Fort Knox with a paperclip) Tarbell reluctantly wandered back to his desk, dejected. In the afternoon Serrin called him back.

  “What are we going to do now?” Serrin asked.

  “I honestly have no idea,” Tarbell replied. “I’m not sure there is anything we can do.” As far as they were concerned, it really was game over. He hung up, crushed.

  A couple of days went by, and Tarbell called Serrin again to discuss something else. At the end of the call, Serrin asked if they had made any headway on the Silk Road server.

  “Nothing,” Tarbell said.

  “And the pass code didn’t work?”

  “What pass code?”

  “The Iceland guys sent a pass code along with the thumb drive,” Serrin explained.

  “You never gave me the pass code!” Tarbell responded, shocked that this was the first he was hearing about this, as the excitement from days earlier returned.

  “I’m pretty sure I did? Here, let me get it,” Serrin said, rustling some papers on his desk. “It’s ‘try to crack this NSA’ with no spaces.” It was a jab at the NSA from the Icelandic authorities after Edward Snowden had leaked a slew of top secret information to the press a few months earlier. When Thom typed the password into the files on the gray thumb drive, they opened like magic, and there, in front of Tarbell’s eyes, was the entire Silk Road server, unencrypted and as plain as day.

  “Holy shit!” Tarbell yelled.

  “Holy shit is right.”

  “It’s open. It’s wide open,” Tarbell said to Serrin over the phone.

  “Hell, yes!” Serrin squealed. “Hell. Yes!”

  As Thom got to work with the other agents, rebuilding the database and setting up a virtual computer that would house the Silk Road, Chris Tarbell wandered into the back room and pulled a giant piece of butcher paper, about eight feet long, from a plotter printer. With the long sheet of paper in hand, he taped it to the wall of lab 1A. He then pulled out a black marker and wrote the words “silk road“ across the top, followed by a series of boxes and numbers below.

  In the same way that the organized-crime FBI agents who had worked out of the Pit decades earlier used to create charts on that same wall noting where mobsters sat in a crime family they were hunting, Tarbell was going to create a chart full of numbers and IP addresses that noted where the servers that belonged to the Silk Road were hidden. And just as in times past when lower-level mobsters would lead the Feds to the Don, the hope was that one of those servers would lead them directly to the Dread Pirate Roberts.

  Chapter 52

  THE FAKE IDS, PART ONE

  July 10, 2013, was a particularly windy day at San Francisco International Airport. Powerful gusts of air rattled planes as they came in over the bay. On some passenger flights the luggage in the hold was jostled around, and on the mail carrier planes, packages and envelopes were shuffled to and fro. But when a Canadian mail flight came in for landing, the wind gusts seemed to stop for a brief moment and the wheels touched down smoothly on the tarmac.

  The plane came to a stop and the cardboard boxes in the hull, filled with envelopes, made their way to the Customs Mail Center at SFO. Inspectors unloaded the boxes one by one and unloaded their contents onto different conveyor belts, all destined for small towns or big cities across the United States.

  The mail handler on duty that day unpacked one of the boxes, reaching for a pile of square envelopes that had remained close together throughout the journey from Canada. Individually each of those square envelopes was not suspect, but together, as a group, something wasn’t right about them.

  What stood out to the mail handler was that the envelopes were exactly the same shape and size, and the handwriting on their fronts was definitively the same, a jagged scribble that had been hastily carved into the labels. But, curiously, the return addresses and names on the envelopes were all slightly and strangely different.

  One was sent from a “Cole Harris” who lived in Vancouver. Another was sent from “Arnold Harris” at a different address in Vancouver. And a third was from “Burt Harris” in still another corner of Vancouver. Three Harrises, all from different areas of Vancouver, all with the same handwriting on the same size envelopes was not only strange; it was suspect. To top off this curiosity, the letters were all addressed to different people in America, including one being sent to an “Andrew Ford,” who lived at 2260 Fifteenth Avenue, right there in San Francisco.

  The mail handler grabbed a seizure form, filled out the appropriate boxes, and then sliced open the envelopes to see what was inside.

  • • •

  Ross had been working around the clock on the site, trying to manage all of the new issues that kept arising, some from disgruntled customers, others related to employees who still weren’t working to their full potential, hackers, dealers who were being arrested by the Feds, and packages that were being seized or stolen somewhere along their routes. He was also gathering anti–law enforcement intelligence from someone called Kevin, who told him that the Feds were starting to arrest some of the biggest vendors on the site.

  Luckily, Ross was safe from all of this chaos, hiding out as Josh in his sublet near the Outer Sunset and able to work around the clock without any questions from his roommates. (Though he did take a few breaks to watch Louis C.K. comedy clips and V for Vendetta again and to read books with libertarian messages that reminded him of his mission.)

  With the confidence Ross now felt, he had started to become stricter with his employees, constantly lecturing some of them to work more productively. “I can do better,” one underling nervously acknowledged after a recent lecture.

  To which Ross replied, “I’m sure you can.”

  Ross, behind the elusive and fearsome mask of the Dread Pirate Roberts, had also decided to do his first interview, hosting a Q&A session with an intrepid reporter from Forbes, Andy Greenberg, who asked DPR questions about the site and its mission. Ross decided to do the Q&A as a text chat so he could run every question by Variety Jones and the two could answer them together. It was the perfect opportunity to spread Ross’s libertarian message and, more important, it was an opportunity to implement VJ’s plan to suggest that there could be more than one Dread Pirate Roberts.

  When Greenberg asked, “What inspired you to start the Silk Road?” Ross cleverly noted, “I didn’t start the Silk Road, my predecessor did,” and then he explained that “everything was in place, he just put the pieces together.”

  “Oh, apologies, I didn’t know you had a predecessor,” Greenberg replied. “When did you take over the Road from him? Before you announced yourself as the Dread Pirate Roberts?”

  Ross continued to spin the tale. “It’s ok,” he wrote back. “This is the first time I’ve stated that publicly.” He told Greenberg that the original creator of the Silk Road was “compensated and happy with our arrangement” and that “it was his idea to pass the torch in fact.” The interview lasted four hours and was the perfect rallying cry for DPR’s mission.

  When Ross wasn’t holed up at home on his laptop, barking orders at his underlings, he would go for long walks in the nearby parks, or hang out with his old Austin friends and new San Francisco pals, a nice reprieve from his other worlds.

  • • •

  Agent Ramirez had worked for the Department of Homeland Security in San Francisco for more than a decade and was by all accounts a seasoned veteran. He always paid attention to the details and always knew the right questions to ask the nefarious peo
ple who came across his path.

  In July 2013 he was working several cases and had just received an e-mail from someone at SFO Customs and Border Protection about a group of square envelopes they had intercepted from Canada. The mail, the e-mail said, had all contained fake IDs, or at least what appeared to be fake.

  Agent Ramirez knew that most of the time customs officials at SFO simply destroyed packages with drugs or fake documents; it was just easier than passing them off to Homeland Security agents. But one of the envelopes had contained nine—nine!—fake IDs. This was a major red flag. Who needs nine fake IDs? One, sure. Two the agent could understand. But nine? The addressee on the particular envelope that was supposed to receive the IDs was an “Andrew Ford,” who apparently lived at 2260 Fifteenth Avenue in San Francisco.

  While the IDs were perfect copies of driver’s licenses from New York, California, Colorado, and the United Kingdom, they all appeared to have a variation of the same person’s face on them: a white man with hazel eyes who stood six feet two inches tall and was born on March 27, 1984. In some pictures the man had a thick beard that had been Photoshopped on, and in others he was clean shaven.

  This was very unusual, Agent Ramirez thought, and after inspecting the documents further, he decided he would go out to the Fifteenth Avenue address and try to find Andrew Ford to question him about the fake licenses.

  • • •

  While months earlier Ross had sworn off Julia, vowing never to speak to her again for telling Erica his secret, he was still undeniably attracted to her. So after they reconnected, he invited her out to visit—a weekend of romance and diversion that Ross needed to take the edge off things. It was at least a month before she’d fly out to San Francisco, so he had time to work out the details, but it was highly unlikely that he’d bring her to his sublet.