In 2011, a twenty-six-year-old libertarian programmer named Ross Ulbricht launched the ultimate free market: the Silk Road, a clandestine Web site hosted on the Dark Web where anyone could trade anything—drugs, hacking software, forged passports, counterfeit cash, poisons—free of the government’s watchful eye.
It wasn’t long before the media got wind of the new Web site where anyone—not just teenagers and weed dealers but terrorists and black hat hackers—could buy and sell contraband detection-free. Spurred by a public outcry, the federal government launched an epic two-year manhunt for the site’s elusive proprietor, with no leads, no witnesses, and no clear jurisdiction. All the investigators knew was that whoever was running the site called himself the Dread Pirate Roberts.
The Silk Road quickly ballooned into $1.2 billion enterprise, and Ross embraced his new role as kingpin. He enlisted a loyal crew of allies in high and low places, all as addicted to the danger and thrill of running an illegal marketplace as their customers were to the heroin they sold. Through his network he got wind of the target on his back and took drastic steps to protect himself—including ordering a hit on a former employee. As Ross made plans to disappear forever, the Feds raced against the clock to catch a man they weren’t sure even existed, searching for a needle in the haystack of the global Internet.
Drawing on exclusive access to key players and two billion digital words and images Ross left behind, Vanity Fair correspondent and New York Times bestselling author Nick Bilton offers a tale filled with twists and turns, lucky breaks and unbelievable close calls. It’s a story of the boy next door’s ambition gone criminal, spurred on by the clash between the new world of libertarian-leaning, anonymous, decentralized Web advocates and the old world of government control, order, and the rule of law. Filled with unforgettable characters and capped by an astonishing climax, American Kingpin might be dismissed as too outrageous for fiction. But it’s all too real.
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The Pink Pill
A tiny pink pill with an etching of a squirrel on either side. Jared Der-Yeghiayan couldn't take his eyes off it.
He stood in a windowless mail room, the Department of Homeland Security badge hanging from his neck illuminated by pulsing halogen lights above. Every thirty seconds, the sound of airplanes rumbled through the air outside. Jared looked like an adolescent with his oversize clothes, buzz cut, and guileless hazel eyes. "We've started to get a couple of them a week," his colleague Mike, a burly Customs and Border Protection officer, said as he handed Jared the envelope that the pill had arrived in.
The envelope was white and square, with a single perforated stamp affixed to the top right corner. heir offen, read the inside flap. Below those two words was the English translation, open here. The recipient's name, typed in black, read david. The package was on its way to a house on West Newport Avenue in Chicago.
It was exactly what Jared had been waiting for since June.
The plane carrying the envelope, KLM flight 611, had landed at Chicago O'Hare International Airport a few hours earlier after a four-thousand-mile journey from the Netherlands. As weary passengers stood up and stretched their arms and legs, baggage handlers twenty feet below them unloaded cargo from the belly of the Boeing 747. Suitcases of all shapes and sizes were ushered in one direction; forty or so blue buckets filled with international mail were sent in another.
Those blue tubs-nicknamed "scrubs" by airport employees-were driven across the tarmac to a prodigious mail storage and sorting facility fifteen minutes away. Their contents-letters to loved ones, business documents, and that white square envelope containing the peculiar pink pill-would pass through that building, past customs, and into the vast logistical arteries of the United States Postal Service. If everything went according to plan, as it did most of the time, that small envelope of drugs, and many like it, would just slip by unnoticed.
But not today. Not on October 5, 2011.
By late afternoon, Mike Weinthaler, a Customs and Border Protection officer, had begun his daily ritual of clocking in for work, pouring an atrocious cup of coffee, and popping open the blue scrubs to look for anything out of the ordinary: a package with a small bulge; return addresses that looked fake; the sound of plastic wrap inside a paper envelope; anything fishy at all. There was nothing scientific about it. There were no high-tech scanners or swabs testing for residue. After a decade in which email had largely outmoded physical mail, the postal service's budgets had been decimated. Fancy technology was a rare treat allocated to the investigation of large packages. And Chicago's mail-sniffing dogs-Shadow and Rogue-came through only a couple of times a month. Instead, whoever was hunting through the scrubs simply reached a hand inside and followed their instincts.
Thirty minutes into his rummaging routine, the white square envelope caught Mike's eye.
He held it up to the lights overhead. The address on the front had been typed, not written by hand. That was generally a telltale sign for customs agents that something was amiss. As Mike knew, addresses are usually typed only for business mail, not personal. The package also had a slight bump, which was suspicious, considering it came from the Netherlands. Mike grabbed an evidence folder and a 6051S seizure form that would allow him to legally open the envelope. Placing a knife in its belly, he gutted it like a fish, dumping out a plastic baggie with a tiny pink pill of ecstasy inside.
Mike had been working in the customs unit for two years and was fully aware that under normal circumstances no one in the federal government would give a flying fuck about one lousy pill. There was, as every government employee in Chicago knew, an unspoken rule that drug agents didn't take on cases that involved fewer than a thousand pills. The U.S. Attorney's Office would scoff at such an investigation. There were bigger busts to pursue.
But Mike had been given clear instructions by someone who was waiting for a pill just like this: Homeland Security agent Jared Der-Yeghiayan.
A few months prior, Mike had come across a similar piece of illicit mail on its way to Minneapolis. He had picked up the phone and called the U.S. Immigration and Customs Enforcement's Homeland Security Investigations office at the airport, half expecting that he would be laughed at or hung up on, as usual. But the HSI agent who answered was surprisingly receptive. At the time, Jared had been on the job for only two months and frankly didn't know any better. "I can't fly to Minneapolis to talk to a guy about one single pill," Jared said. "So call me if you get something in my area, in Chicago. Then I can go over there and do a knock-and-talk."
Four months later, when Mike found a pill destined for Chicago, Jared rushed over to see it. "Why do you want this?" Mike asked Jared. "All the other agents say no; people have been saying no to meth and heroin for years. And yet you want this one little pill?"
Jared knew very well that this could be nothing. Maybe an idiot kid in the Netherlands was sending a few friends some MDMA. But he also wondered why one single pill had been sent on such a long journey and how the people who mailed such small packages of drugs knew the recipients they were sending them to. Something about it felt peculiar. "There may be something else to this," Jared told Mike as he took the envelope. He would need it to show his "babysitter."
Every newbie agent in HSI was assigned one-a training officer-during their first year. A more seasoned officer who knew the drill, made sure you didn't get into too much trouble, and often made you feel like a total piece of shit. Every morning Jared had to call his chaperone and tell him what he was working on that day. The only thing that made it different from preschool was that you got to carry a gun.
Unsurprisingly, Jared's training officer saw no urgency to a single pill, and it was a week before he even consented to accompany his younger colleague on the "knock-and-talk"-to knock on the door of the person who was supposed to receive the pill and, hopefully, talk with them.
That day, as Jared's government-issued Crown Victoria zigzagged through the North Side of Chicago, the small Rubik's Cube that hung from his key chain swung back and forth in the opposite direction. His car radio was dialed into sports: the Cubs and White Sox had been eliminated from contention, but the Bears were preparing for an in-division contest against the Lions. Amid the crackle of the radio, he turned onto West Newport Avenue, a long row of two-story limestone buildings split into a dyad of top- and bottom-floor apartments. Jared knew this working-class neighborhood well. He'd followed the baseball games at nearby Wrigley Field when he was a kid. But now this was Hipsterville, full of fancy coffee shops, chic restaurants, and, as Jared was now learning, people who had drugs mailed to their houses from the Netherlands.
He was fully aware how ridiculous he might look in the eyes of his grizzled training officer. They were in one of the city's safest precincts to question someone about a single pill of ecstasy. But Jared didn't care what his supervisor thought; he had a hunch that this was bigger than one little pill. He just didn't know how big-yet.
He found the address and pulled over, his chaperone close behind. They wandered up the steps and Jared tapped on the glass door of apartment number 1. This was the easy part, knocking. Getting someone to talk would be a whole different challenge. The recipient of the envelope could easily deny that the package was his. Then it was game over.
After twenty seconds the door lock clicked open and a young, skinny man dressed in jeans and a T-shirt peered outside. Jared flashed his badge, introduced himself as an HSI agent, and asked if David, the man whose name was typed on the white envelope, was home.
"He's at work right now," the young man replied, opening the door further. "But I'm his roommate."
"Can we come inside?" Jared asked. "We'd just like to ask you a few questions." The roommate obliged, stepping to the side as they walked toward the kitchen. As Jared took a seat he pulled out a pen and notepad and asked, "Does your roommate get a lot of packages in the mail?"
"Yeah, from time to time."
"Well," Jared said as he glanced at his training officer, who sat silently in the corner with his arms crossed, "we found this package that was addressed to him and it had some drugs inside."
"Yeah, I know about that," the roommate replied nonchalantly. Jared was taken aback by how casually the young man admitted to receiving drugs in the mail, but he continued with the questions, asking where they got these drugs from.
"From a Web site."
"What's the Web site?"
"The Silk Road," the roommate said.
Jared stared back, confused. The Silk Road? He had never heard of it before. In fact, Jared had never heard of any Web site where you could buy drugs online, and he wondered if he was just being a clueless newbie, or if this was how you bought drugs in Hipsterville these days.
"What's the Silk Road?" Jared asked, trying not to sound too oblivious but sounding completely oblivious.
And with the velocity of those descending airliners at O'Hare, the skinny roommate began a fast-paced explanation of the Silk Road Web site. "You can buy any drug imaginable on the site," he said, some of which he had tried with his roommate-including marijuana, meth, and the little pink ecstasy pills that had been arriving, week after week, on KLM flight 611. As Jared scribbled in his notepad, the roommate continued to talk at a swift clip. You paid for the drugs with this online digital currency called Bitcoin, and you shopped using an anonymous Web browser called Tor. Anyone could go onto the Silk Road Web site, select from the hundreds of different kinds of drugs they offered and pay for them, and a few days later the United States Postal Service would drop them into your mailbox. Then you sniffed, inhaled, swallowed, drank, or injected whatever came your way. "It's like Amazon.com," the roommate said, "but for drugs."
Jared was amazed and slightly skeptical that this virtual marketplace existed in the darkest recesses of the Web. It will be shut down within a week, he thought. After a few more questions, he thanked the roommate for his time and left with his colleague, who hadn't said a word.
"Have you ever heard of this Silk Road?" Jared asked his training officer as they walked back to their respective cruisers.
"Oh yeah," he replied dispassionately. "Everyone's heard of Silk Road. There must be hundreds of open cases on it."
Jared, somewhat embarrassed at having admitted he knew nothing about it, wasn't deterred. "I'm going to look into it anyway and see what I can find out," he said. The older man shrugged and drove off.
An hour later Jared bounded into his windowless office, where he waited for what seemed an eternity for his archaic Dell government computer to load up. He began searching the Department of Homeland Security database for open investigations on the Silk Road. But to his surprise, there were no results. He tried other key words and variations on the spelling of the site. Nothing. What about a different input box? Still nothing. He was confused. There were not "hundreds of open cases" on the Silk Road, as his training officer had claimed. There were none.
Jared thought for a moment and then decided to go to the next-best technology that any seasoned government official uses to search for something important: Google. The first few results were historical Web sites referencing the ancient trade route between China and the Mediterranean. But halfway down the page he saw a link to an article from early June of that year on Gawker, a news and gossip blog, proclaiming that the Silk Road was "the underground website where you can buy any drug imaginable." The blog post showed screenshots of a Web page with a green camel logo in the corner. It also displayed pictures of a cornucopia of drugs, 340 "items" in all, including Afghan hash, Sour 13 weed, LSD, ecstasy, eight-balls of cocaine, and black tar heroin. Sellers were located all over the world; buyers too. You've got to be fucking kidding me, Jared thought. It's this easy to buy drugs online? He then spent the entire rest of the day, and most of the evening, reading anything he could about the Silk Road.
Over the weekend, as he drove between antique fairs (his weekly ritual) near Chicago with his wife and young son, he was almost catatonically consumed with the drug Web site. Jared realized that if anyone could buy drugs on the Silk Road, anyone would: from middle-aged yuppies who lived on the North Side of Chicago to young kids growing up in the heartland. And if drugs were being sold on the site now, why not other contraband next? Maybe it would be guns, bombs, or poisons. Maybe, he imagined, terrorists could use it to create another 9/11. As he looked at his sleeping son in the rearview mirror, these thoughts petrified him.
But where do you even start on the Internet, in a world of complete anonymity?
Finally, as the weekend came to a close, Jared started to formulate an idea for how he could approach the case. He knew it would be laborious and tedious, but there was a chance that it could also eventually lead him to the creator of the Silk Road Web site.
But finding the drugs and the drug dealers, and even the founder of the Silk Road, would be easy compared with the challenge of persuading his supervisor to let him work this case based on a single tiny pink pill. Even if he could convince his boss, Jared would also have to cajole the U.S. Attorney's Office into supporting him in this pursuit. And there wasn't a U.S. attorney in all of America who would take on a case that involved one measly pill of anything. Exacerbating all of this was the fact that thirty-year-old Jared was as green as they came. And no one ever-ever!-took a newbie seriously.
He would need a way to convince them all that this was bigger than a single pink pill.
By Monday morning he had come up with a scheme that he hoped his boss would not be able to ignore. He took a deep breath, walked into his supervisor's office, and sat down. "You got a minute?" he said as he threw the white envelope on the desk. "I have something important I need to show you."
Table of Contents
Author's Note xiii
Cast of Characters xv
1 The Pink Pill 3
2 Ross Ulbricht 13
3 Julia Vie 17
4 The Debate 21
5 Jared's Khat 24
6 The Bonfire 28
7 The Silk Road 33
8 Ross the Farmer 37
9 Opening Day of the Silk Road 42
10 What Goes Up Must Come Down 47
11 The Gawker Article 50
12 A Bull's-eye on My Back 54
13 Julia Tells Erica 58
14 What Have You Done?! 62
15 Jared and the Fifty-Ton Flamingo 65
16 From Austin to Australia 69
17 Carl Force's Tomorrow 75
18 Variety Jones and the Serpent 78
19 Jared Goes Shopping 83
20 The Dread Pirate Roberts 86
21 Carl Force Is Born Again 90
22 "O Captain, My Captain" 92
23 Ross, Hanged or Home 95
24 Carl, Eladio, and Nob 100
25 Jared's Chicago Versus Carl's Baltimore 103
26 The Mutiny 107
27 A Billion Dollars?! 112
28 The Aspiring Billionaire in Costa Rica 115
29 Variety Jones Goes to Scotland 119
30 The Armory Opens 123
31 Ross Silences Julia 127
32 Chris Tarhell, FBI 133
33 Ross Arrives in San Francisco 137
34 Chris in the Pit 142
35 Batten Down the Hatches! 145
36 Jared's Dead Ends 150
37 A Pirate in Dominica 153
38 Carl Likes DPR 159
39 Kidney for Sale! 165
40 The White House in Utah 171
41 Curtis Is Tortured 176
42 The First Murder 180
43 The FBI Joins the Hunt 184
44 Camping and the Ball 187
45 Gary Alford, IRS 195
46 Life and Death on the Road 199
47 Gary's Big Change 203
48 Ross Goes Underground 207
49 Carl Switches Teams 213
50 A Parking Ticket on the Internet 217
51 Tarbell Finds a Mistake 221
52 The Fake IDs, Part One 225
53 The Deconfliction Meeting 231
54 Jared Becomes Cirrus 237
55 Julia Is Saved! Hallelujah! 242
56 The Fake IDs, Part Two 245
57 Onward to Federal Plaza 249
58 Julia Comes to San Francisco 254
59 I Am God 258
60 The Phone Call 262
61 The Good-bye Party 269
62 The Pink Sunset 275
63 Carla Sophia 279
64 FeLiNa 282
65 Arrested 290
66 The Laptop 293
67 Ross Locked Up 296
68 United States of America v. Ross William Ulbricht 300
69 To Catch a Pirate 304
70 Sentencing 307
71 The Plural of Mongoose 310
72 The Museum 313
73 The Others 316
Notes on Reporting 323