American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road

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.”

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