American Kingpin

  “Wow, this place is amazing,” he said as Julia waltzed around in front of him.

  “I know. Aren’t you proud of me?” she replied ebulliently. “I’m dating a new guy now. He takes me on all of these trips and takes me to all these great dinners.”

  “Way to make me feel awesome,” Ross said, joking with her, and then quipped, “Well, I’m dating a girl too.”

  After some small talk, Ross asked if they could go for a walk to discuss something. “Of course.” Julia beamed as she grabbed his hand and they strolled out of the building, down the concrete steps, and across the street toward a dirt path that led to Lady Bird Lake.

  The sun was beginning to set as they meandered along the trail, hand in hand, telling stories about the past few months of their lives. Julia was still in love with Ross, and part of her hoped he had come to take her back. They eventually came across a tree that was wider than Ross stood tall. At its base there was a huge rock that rested on the water’s edge. They sat down together.

  “So,” Ross said as he took a deep breath, preparing to tell Julia something important. “I just want you to know that I quit the site—I quit the Silk Road.”

  “Thank God! That’s so wonderful.” She leaned over and gave Ross a huge hug, holding on to him for as long as she could.

  The leaves above them sighed in the breeze as Ross looked out at the sun that reflected pink and yellow and orange off the water. He took another deep breath and began an explanation of why he had given up the site. It had grown too big; it was too stressful; it just felt right to pass it along to someone else. “I’m so sorry for telling you about it in the first place,” he lamented, “and I take full responsibility—”

  “Thank you,” Julia said as he continued to talk, and tears began welling up in her eyes.

  “I just felt so powerful running the site,” he said, then paused, as if he were reciting lines in a play. “I’m sorry.”

  Julia thanked him again, both for the apology and for quitting the Silk Road. She leaned over and they started to kiss. After a few moments Ross pulled back and looked her in the eyes. “I just need to know one more thing,” he said. “Did you tell anyone else about the site? Anyone other than Erica?”

  “No,” she responded quickly.

  “No one?”

  “No. I didn’t tell anyone else. Just Erica.” A pang of guilt came over her for having betrayed the secret at all. “I love you, Ross.”

  “I love you too,” he said as they continued kissing, the sun lowering into the horizon behind them. “I just couldn’t move on without knowing that no one else knew.”

  They spoke more about the past, and Ross told her about his travels—about Thailand and the beaches and jungles and a mountainous sculpture he’d seen that was made entirely of extra-large dildos; about Australia, picnicking with his sister, and that his travels had made him reflect upon his life and how thankful he was that he no longer had anything to do with the Silk Road.

  The cold air was beginning to blow off the water and Ross suggested they walk back.

  “So what are you going to do now?” Julia asked as they crossed Rainey Street back toward her apartment building.

  Ross told her he was leaving Texas in a few days to move to San Francisco. He planned to build an app with an old friend from Austin, René Pinnell. “I probably won’t see you again for a while,” he told her solemnly.

  She would be sad to see him go, she explained, but happy for him that he was free from the clutches of that awful Web site.

  “Yeah,” he agreed, “I’m glad to be rid of it too; it was too stressful.”

  As they approached the door to the studio, Ross leaned in and kissed Julia one last time. “I love you,” she said. He didn’t reply. He just held her there for a second and then turned around and walked away. Heading into the darkness, alone.

  PART III

  Chapter 32

  CHRIS TARBELL, FBI

  A question had been plaguing Chris Tarbell all day—in the office, at lunch, and now as he walked through downtown Manhattan with his coworkers. As the group crossed Broadway and turned right onto Center Street, he just couldn’t stop himself; he had to ask. “Okay,” he said to the men around him, “if you had to . . .” But before he could finish, they all began wincing, knowing full well what was coming. A “would you rather” joke from Tarbell was usually a distasteful, often comical query that always landed at a moment his colleagues least expected, intentionally catching them completely off guard. These often-crass jokes could range from the truly unpalatable to the truly bizarre. “Would you rather: sleep with your mother, or sleep with your father?” “Would you rather: be half your height, or double your weight?” “Would you rather have an erection for a year or hiccups for the rest of your life?”

  “Where do you come up with this shit, Tarbell?” one of his coworkers asked.

  “Come on. If you had to—like, you had no choice,” Tarbell continued, as they kept walking, his colleagues grimacing as Tarbell harangued them with questions like an older brother tormenting his younger siblings.

  The badgering briefly stopped when the group came upon the Whiskey Tavern, a local dive bar on Baxter Street, sandwiched between two bail-bond storefronts that looked out on the New York Police Department.

  All the cops and government employees in New York had local watering holes they burrowed into after work. The FDNY went to Social Bar on Eighth Avenue, the NYPD had Plug Uglies on Third, and the Cyber Division of the FBI’s New York office lived at the Whiskey Tavern. Special Agent Chris Tarbell of the FBI and his team of agents frequented the shit-hole dive bar at least five nights a week.

  When they arrived, Meg, the freckled bartender, would greet them with a “Hello, boys,” then let them know, “The back room is all yours.” The area of the bar she was referring to was always reserved for the FBI cybercrime crew, and if they arrived unannounced, Meg would evict whoever was there.

  Given that tonight was a special evening, Tarbell asked for a few bottles of champagne, pronounced “cham-pag-nay.” (By “champagne” he meant Miller High Life—the so-called champagne of beers, which cost $4 a pint at the tavern.)

  Most of the FBI agents at the bar dressed the same, wearing oversize dark suits and white button-down shirts, and could have easily passed for bankers or lawyers. That was not true of Chris Tarbell, who looked like a cop from ten city blocks away with his short buzz cut, young face that didn’t seem to fit his stocky 250-pound body, and swagger that exuded confidence.

  As they settled in for a night of revelry, it was Tarbell who was the star of the show. After all, he was the one responsible for recently taking down an infamous hacker group, called LulzSec, that the media and security experts had asserted could never be stopped. What made LulzSec so special was that, unlike hackers of the past who would break into an institution for financial gain, this nefarious crew had spent the past year ransacking the Internet for the “lulz,” a neologism that essentially meant “a good laugh.” Part of their comedic hacking had included knocking the CIA Web site off-line, breaking into Sony Pictures servers, and defacing the Web sites of the British newspapers the Times and the Sun by posting a fake news story that Rupert Murdoch had died. All just for fun.

  But after months of undercover work, Chris Tarbell and his FBI team had systematically arrested the people behind LulzSec all across the world—in Chicago, Ireland, and New York City. Which is why the gang was celebrating at the Whiskey Tavern.

  In the back of the bar, Meg reappeared with a dirty black tray crowded with twenty shot glasses, half of them filled with cheap whiskey, the other half with green pickle juice. She dropped the concoction, known as the Pickle Back, a bar specialty, on the table.

  “Whose turn is it to drink the tray?” Tarbell bellowed to the group of men around him, all of whom responded with another wince.

  Years earlier Tarbell had inv
ented this ritual—known as the “drinking of the tray”—wherein someone was expected to drink the slushy potion of pickle juice, whiskey, and any other liquid that had been sloshing on the tray before the drinks were served. If no one else had the guts to do it, Tarbell was always up for the sickening challenge.

  At thirty-one years old, Tarbell had already made a big name for himself as one of the top cybercrime agents in the FBI, if not the world. Sure, he’d landed the LulzSec case by chance when a tip came in through a hotline and Tarbell was the lucky one to pick up the phone. But it was what he did with that information that separated him from the other agents—turning the top hacker of LulzSec, a man who was known as Sabu, and then using him to bring down the entire organization. Because of Tarbell’s ability to find people online, the media would soon bestow on him the nickname “the Eliot Ness of cyberspace,” after the renowned American Prohibition agent.

  It was no accident that Tarbell had ended up where he was, rising through the ranks of the FBI. He had planned it this way, just as he planned everything. Tarbell had worked hard to earn his master’s degree in computer science, then became a cop. After more than a decade of eighteen-hour days, he had made his way up through the FBI to become a special agent. And he didn’t stop there. When he wasn’t with his wife and kids, he continued to study computer forensics for any technology platform imaginable.

  He endured this because, more than anything, he desired to be the absolute best at anything he put his mind to. If his gym buddy was able to bench-press 400 pounds, Tarbell would spend months of his life lifting weights until he could bench-press 450 pounds (which he could actually do).

  Over time he learned that the way to have a leg up on everyone else was to anticipate something before it happened and then have the answer to it. He prepped for everything. The night before he took his SATs in high school he did a practice drive to the test site to ensure he arrived on time. He did this the day before his physical test for the FBI. During his first few weeks at the Bureau he created a meticulous map of the entire office, labeling who everyone was and what he needed to know about them.

  This obsessive planning came home with him. He told his wife, Sabrina, that the couple needed a code word they could use in case anything ever went wrong. “‘Quicksand,’” he told her. “That’s the word we use with each other if we’re ever in trouble: ‘quicksand.’” And when the cybercrime boys went out drinking, Tarbell texted ahead to let freckled Meg know how many people to expect. Nothing like planning a party at a dive bar.

  On this particular night as many as fifty government employees were at the Whiskey Tavern to celebrate the capture of the LulzSec crew. As Tarbell sat there licking the taste of pickles and whiskey off his lips, Tom Brown, the assistant U.S. attorney for the Southern District of New York. who would end up prosecuting the LulzSec hackers, wandered over.

  “So, Tarbell,” Tom said, preparing to ask a question that had been plaguing him all day. “What’s next? Who are we going after next?”

  Tarbell looked back, annoyed. He had just spent the past few months of his life working twenty-hour days trying to take down LulzSec, and Tom was already badgering him about the next target. “Come on,” Tarbell said. “We just fucking finished a case. Can’t we just celebrate first?”

  “Of course you can,” Tom replied glacially, taking a short sip from his drink, “but I just wanted to see what we were going to do after that.”

  Tom was clearly baiting Tarbell and already knew the answer. “There is a target no one has been able to crack,” Tom said, explaining that “no one” included the DEA, HSI, and a handful of government agencies from around the globe. The cybercrime FBI agents sipped from their cham-pag-nay as they listened to what Tom was saying. “I think,” he said, “we should start looking at the Silk Road next.”

  Chapter 33

  ROSS ARRIVES IN SAN FRANCISCO

  The Alamo Square neighborhood of San Francisco has long been considered one of the city’s most beautiful. The few blocks that make up the modest district sit snugly near the center of the city, framed by the past and with views of the future. The square is lined with bright “painted lady” Victorian homes built in the late 1800s, thanks in part to money from the Gold Rush years earlier. To the east, across gritty Market Street, modern glass skyscrapers are erected almost daily to house the fortunes being minted by the new gold rush—a wave of handsomely funded private companies, many of them valued at more than $1 billion, so-called unicorns. After the bubble had popped years earlier, there had been a resurrection of start-ups returning to the city, and billions of dollars ready to fund them.

  On a bright and chilly afternoon in the summer of 2012, in the park in the middle of Alamo Square, a group of children giggled as they bounced through the playground, and unleashed dogs barked as they chased one another on the hilltop. And there, amid this happiness, Ross Ulbricht lay on the grass, inhaling his new city.

  Ross fell in love with the Bay Area from almost the moment his feet touched the ground in San Francisco. Everything looked so magical and new. The flat, prairielike avenues of Texas were replaced by streets that seemed to undulate like a never-ending roller coaster. The billboards along the freeway didn’t talk about NASCAR, Jesus, or the best rib-eye steak in town but rather advertised mystical search engines, social networks, and even new digital currencies.

  He had arrived in this wonderful universe a few weeks earlier, wide-eyed and full of vigor. All he owned now was a small bag of clothes and his laptop. He felt as free as he ever had: the homeless kingpin of one of the fastest-growing drug empires in the world.

  The decision about where to stay was simple. His pal from Austin, René Pinnell, who now lived in San Francisco, and his girlfriend, Selena, offered up a spare room in their small but welcoming apartment. Soon after Ross unpacked his few belongings, the three friends settled into a new routine, spending evenings exploring the city, cooking dinner, and talking about the meaning of life. (There was, however, one thing Ross didn’t talk about: the Silk Road. He was never going to make that mistake again.) They played card games together, Twister, Scrabble (Ross often won), and hugged each other good night.

  After breakfast each morning, while René and Selena sauntered off to work, their new roommate, Ross, would wave good-bye and wander down the street to a nearby coffee shop to oversee his drug empire.

  The safest place he had found to work was a small café on Laguna Street called Momi Toby’s, which was conveniently located a block from René’s apartment on Hickory Street. Momi Toby’s (pronounced “mow-mee toe-bees”) resembled a French bistro with small tables and chairs outside. Inside, the Wi-Fi was free, and lots of seating allowed Ross to have his back against the wall so no one could see his computer screen, and subsequently the Silk Road.

  As the weeks went on, Ross made new friends in the city, which carried some stress. While he couldn’t talk to them about what he did for work, he could discuss what inspired him to do it. After all, in San Francisco the mentality of using technology to try to disrupt a broken system wasn’t a strange way of thinking but rather the norm. In so many ways, the programmers and entrepreneurs Ross met were just like him.

  They looked at the world around them and saw that the government was a ball of wasteful red tape; that the taxi industry treated customers like shit; hotels overcharged and overtaxed; health care was a sham, driven by the needs of the insurance agencies, not the sick; oil-dependent cars had helped to justify an eternal war in the Middle East; and illegal drugs were only illegal because the government wanted to control the people. And all of these issues were a result of the previous generations’ mistakes. Their parents had inextricably fucked up the world we lived in, and it was the people in San Francisco—those just like Ross—who were going to use technology to fix it all.

  You’re fucking welcome!

  He was also invigorated by the manifestation of the libertarian ideals around him t
hat the start-ups were employing. And here was Ross, doing the exact same thing, but instead of taxis or hotels, health care or gas-guzzling cars, he was trying to defeat the U.S. government and its pathetic, destructive war on drugs.

  The CEOs of these other start-ups were no different from Ross, either. They had all read the same Ayn Rand books. These chief executives shared the same quotes on Facebook as he did: “The question isn’t who is going to let me; it’s who is going to stop me.” The leaders of these companies all preached the same verbiage as the Dread Pirate Roberts too, on their blogs and in their press releases: “Let the market decide; not the government.” “Let the people determine who should win; not the politicians.” “We’re changing the world and making it a better place.”

  Most of all, the new friendships he was making were the perfect antidote to the problems he was now experiencing on the Silk Road. Sadly, his closest confidant was starting to rub him the wrong way. Not only was Variety Jones not okay with selling H, which went against Ross’s entire libertarian philosophy behind the Silk Road, but VJ also proclaimed that sure, while he was there to help Dread free people from the clutches of government, they were still, at the end of the day, drug dealers.

  Ross vehemently disagreed. “As long as we don’t cross [a] line in our pursuit,” DPR wrote to Variety Jones, “then we are only doing good.”

  “Ha, dude, we’re criminal drug dealers,” VJ responded. “What line shouldn’t we cross?”

  “Murder, theft, cheating, lying; hurting people,” DPR replied, resentful of the question. “That line. We are drawing a new line I guess you could say. According to that line, we aren’t criminals.”

  This discussion echoed another suggestion from VJ, that Ross should put a powerful lawyer on the payroll. “You need to pick a top man, a top man in his field, with top man contacts,” Jones wrote. “That field is interstate drug smuggling, money laundering, RICO and drug kingpin legislation.” But in Ross’s mind, he wasn’t going to get caught, so why would he need a “top man” lawyer? That was already admitting defeat.