Charged with narcotics trafficking, money laundering, computer hacking and attempted murder, Ulbricht faces life in prison. When the New York judge denied bail, his family, who had raised $1 million in bail money pledged from Ulbricht's many supporters, gasped. It was impossible to believe that Dread Pirate Roberts could be him. "In his entire life, with all these people who know him, something would have been indicated that he was capable of this," his mother, Lyn, tells me, "and it never has."
Growing up in Austin, Ulbricht was, his father, Kirk, recalls, "a healthy, happy, unflappable Buddha of a kid." His parents built and rented bamboo solar-powered houses on the Costa Rican coast, and Ulbricht spent his summers running barefoot among the monkeys and learning from his dad how to be a big-wave rider. "He would go out surfing, and I'd be on binoculars and say, 'Get in here now,'" his mother recalls. "Because he's so enthusiastic, sometimes he's a little too fearless."
But Ulbricht had a geeky side as well. He later recalled feeling like "a dorky kid." An Eagle Scout like his dad and a comic-book fanatic, he won the third-grade math olympics in school. Ulbricht spent hours doodling monsters in notebooks and was more interested in painting miniatures for the fantasy board game Warhammer than playing video games. "We didn't want our kids on the computer," says Kirk. "We wanted them outside playing." Taking a cue from his parents, Ulbricht was an entrepreneurial kid, selling ice pops and magazine subscriptions door to door.
By high school, "Rossman," as he was known to his friends, had become an easygoing and fun-loving Austin hipster, skateboarding with friends, one of whom shaved Ulbricht's hair into a mohawk on a whim. On some weekends, his crew would pile into trucks and drive out to a hill-country ranch to party. Classmate Sean Gaulager recalls Ulbricht leaping over a bonfire and dabbling in hallucinogens. "Ross, to me, was always a fucking awesome dude," Gaulager says. When another friend, René Pinnell, told Ulbricht how he had merely "dipped a toe" in drinking and drugs during high school, Ulbricht told him that "I did, like, a cannonball . . . in that department."
But Ulbricht was always able to balance partying with grades. Graduating with a 1460 SAT score, he earned a full scholarship to the University of Texas at Dallas, where he became, as one friend puts it, a "physics hippie." Making a name for himself at the college's NanoTech Institute, where he published papers on solarcell technology, Ulbricht strolled around campus shirtless and barefoot, ingested mind-spinning psychedelics and spouted Eastern philosophy. He loved staying up late watching trippy movies like Richard Linklater's Waking Life and talking about the nature of reality. "My whole philosophy at the time," he later recalled, was "of being super-open and loving and connected to everything."
He graduated in 2006 and won another full scholarship to Penn State to pursue a master's in materials science and engineering. While researching thin-film crystals as a research scientist, Ulbricht grew a scraggly beard, practiced yoga and took up conga drumming. He felt, as he posted on Facebook, "overwhelmed with the glory of being alive."
He was also evolving into a hardcore libertarian. In 2007, when Mitt Romney posed a question on YouTube, asking, "What do you believe is America's single greatest challenge?" Ulbricht sat in front of his webcam and said, "The most important thing is getting us out of the United Nations," which he saw as somehow impeding political freedom. He would eventually discover the work of Ludwig von Mises and the Austrian School of economics, which further crystallized his beliefs.
By the time he finished his master's in 2009, he had become disillusioned with being a scientist. "It wasn't for him," his mother says. "He wanted to be an entrepreneur." When family and friends questioned him about his change of course, Ulbricht remained adamant. "I remember him saying, 'I just don't want to do this,'" his lifelong friend Alden Schiller recalls. "He didn't like the idea of being an employee, or being in the lab setting." Moving back to Austin, he started his own used-book company, Good Wagon, donating a portion of the proceeds to an inner-city-youth program and leftover books to a prison-literacy project. "We raised him to be empathetic," his mother says, proudly, "and to put yourself in others' shoes." One day, however, Ulbricht walked into his company warehouse to find that the shelves had collapsed. Thousands of books he'd spent weeks organizing were a mess, and it would take an ungodly amount of hours to put them back into place. Ulbricht seemed to see it as a sign and closed the business. As his mother says, "He thought, 'I've got to do something else.'"
Silk Road was rooted in its founder's frustration over, as he wrote, "what seemed to be insurmountable barriers between the world today and the world I wanted." He'd begun working on the idea in 2010, inspired by his libertarian beliefs. "All of the sudden, it was so clear," he went on. "Every action you take outside the scope of government control strengthens the market and weakens the state." And the action he decided to take was in creating a marketplace for personal liberties online.
According to prosecutors, a journal found by the FBI on Ulbricht's computer stated that he wanted "to create a website where people could buy anything anonymously, with no trail whatsoever that could lead back to them." At first, he thought to call it Underground Brokers, but then divined a better name, something that sounded more eternal. "Silk Road is going to become a phenomenon," he wrote, "and at least one person will tell me about it, unknowing that I was its creator."
In January 2011, an announcement appeared online for the launch of Silk Road, explaining how to use the Tor browser to connect to it. "Every precaution is made to ensure your anonymity and security," it read. The same month, a user named Altoid (prosecutors believe this to be an alias for Ulbricht himself) spread the word on online forums, comparing Silk Road to "an anonymous Amazon.com."
Silk Road wasn't just a place to buy dope; it was a well-designed and well-organized shop. There were rules. Child porn was not permitted, nor were stolen items. Drugs were broken down into discrete sections: cannabis, dissociatives, Ecstasy, psychedelics, opioids, stimulants.
Like eBay, Silk Road implemented seller ratings for quality control. For more assurance, industrious dealers offered samples of their products to prospective reviewers, who could then post accounts of their highs (or lows). Products would arrive by post, often with bogus return addresses. Drugs would be slipped inside DVD cases, lip-balm dispensers and other decoys.
It wasn't just the efficient shopping experience that customers liked, it was their fearless leader, too. The site's as-yet-unnamed founder was an active presence, attentively addressing his customers' concerns and rallying them around the brave new world they were creating. "There are heroes among us here at Silk Road," he wrote in one post. "Every day they risk their lives, fortunes and precious liberty for us."
At times, the founder sounded like he was giving a stump speech. "Silk Road is about something much bigger than thumbing your nose at the man and getting your drugs anyway," he wrote. "It's about taking back our liberty and our dignity and demanding justice." He seemed to have a politician's talent for creating a good-natured sense of false intimacy. When a customer asked for a virtual embrace, the benevolent leader replied, "Hugs not drugs. . . . No wait, hugs AND drugs!"
As traffic flooded the site, it wasn't only drug dealers and buyers who took notice. After a Gawker story ran about Silk Road in June 2011, New York Sen. Chuck Schumer demanded the site be shut down. "[It] represents the most brazen attempt to peddle drugs online that we have ever seen," he told the press.
The feds soon began to quietly monitor the site's activities. In January 2012, 32-year-old Jacob Theodore George IV, a Maryland-based Silk Road dealer, was busted by federal agents. As part of his plea, which was only recently made public, he turned over his e-mails, financial records and shipping details – a bounty of insight into Silk Road's underworld.
But the feds kept the bust quiet, building their case, and Silk Road's business continued unabated. As revenues increased, the site announced a change in the commission structure, shifting from a flat rate to a sliding scale based on the price of sales items (10 percent of the first $50 to 1.5 percent for sales more than $1,000). When the community balked, their leader didn't hesitate to remind them who was boss. "Whether you like it or not, I am the captain of this ship," he wrote. "If you don't like the rules of the game, or you don't trust the captain, you can get off the boat."
Soon, the site had taken on a life of its own, so much so that its elusive creator told his followers that it was time for a symbolic change. "Silk Road has matured, and I need an identity separate from the site," the administrator wrote. "I am Silk Road, the market, the person, the enterprise, everything. But I need a name."
He took one from a character in The Princess Bride: Dread Pirate Roberts, a fearsome pirate whose name was not just his own but one to be passed on to others who might succeed him. "Drumroll please . . . ," he wrote. "My new name is: Dread Pirate Roberts."
Throughout this time, Ulbricht seemed like the same old Ross, though his hippie persona had taken on an edge of grandiosity. "Who is the smartest, most talented programmer you know?" he posted on Facebook in October 2011. "Tell them your awesome Facebook friend Ross is recruiting for a seed-funded Bitcoin startup company. Thanks." When his friend Noah replied by asking what Ulbricht was doing, Ulbricht brushed it off. "Don't worry, Mr. Noah," he wrote. "Just find me some programmers! You can Google 'Bitcoin.'"
A posting on his LinkedIn page was similarly mysterious. "I want to use economic theory as a means to abolish the use of coercion and aggression amongst mankind," he wrote. "The most widespread and systemic use of force is amongst institutions and governments. The best way to change a government is to change the minds of the governed. To that end, I am creating an economic simulation to give people a firsthand experience of what it would be like to live in a world without the systemic use of force." Ulbricht spent hours alone, standing barefoot on a hard floor at a stand-up desk. In one apartment, he had his keyboard, monitor and mouse stacked on wobbly piles of books; to his right was a thrift-store painting of a blue peacock. He worked for so long that he nibbled away his fingernails and his feet throbbed – until a friend suggested he wear sandals. When he wasn't working, he could be found playing poker on rooftops, or frequenting local music haunts. He went to the Austin City Limits festival, lounging with buddies in the grass in an undershirt and gray fedora. He was dating an attractive photographer, Sarah Allen, whom he'd met at an African drumming club.
"He was so sweet and loving and so good-looking and intelligent," Allen tells me. They went swimming in Barton Springs, did yoga outside and spent long nights partying with Allen's models at her studio. "I would start singing and dancing," model Samantha Schreibvogel recalls. "It wouldn't take him long before he'd be dancing with me."
Following a rocky patch with Allen, Ulbricht sold his black Ford F150 and, in November 2011, he moved to Australia, where his older sister, Cally, was living. The two had always been close and had even applied to go on the Amazing Race TV show together. "We were always a team," she tells me. Ulbricht still lived like a student. "He didn't buy much," Cally says with a laugh. "He's been wearing the same clothes for 20 years." Ulbricht spent months surfing the local beaches. "Forecast: warmth and smiles," he posted on Facebook. "It's sunny again!!!" But he was less forthcoming about how he was paying the bills. "I thought he was working with foreign currencies, but I don't really know what that means," Cally says. Their mother just knew that he was doing some kind of financial work on the computer. "When he would explain things, I was like, 'Oh, OK, whatever,'" Lyn says. "He doesn't tell his mother everything."
One of the few people whom Dread Pirate Roberts, or DPR, trusted was Curtis Clark Green, who lived with his wife in a comfortable house in Spanish Fork, Utah. Green claimed to be a former paramedic and started posting on Silk Road forums in June 2011 as the site's drug sage. Using the handles Chronicpain and Flush, he often alluded to his enjoyment of self-medicating with opioids and to having suffered an undisclosed "accident" that sidelined his plans to complete a nursing degree. Green doled out advice on how to get maximum highs with minimum overdose risk and the best places on the body to shoot up ("Don't use your feet. Blood clots can form very easily if it's done this way"). When he put pharmaceutical fentanyl up on Silk Road, he promised to "personally test each batch to make sure it's up to par."
In the summer of 2012, after news surfaced of the first public arrest of a Silk Road user – 32-year-old Paul Leslie Howard, charged with trafficking coke and Ecstasy through the site – DPR appeared to realize that Silk Road was now on the feds' radar and that he needed someone to help run his operation. By the end of 2012, Green was on payroll. According to prosecutors, when DPR got a message that December from a new seller looking to unload large quantities of cocaine, he put Green on the job of brokering the deal. "We have a buyer for you," DPR wrote the seller. "One of my staff is sending the details."
Though DPR was careful to keep a distance from his customers, he occasionally lifted the veil slightly – after Green helped the seller unload a kilo of coke to a buyer for $27,000 worth of Bitcoins, DPR reached out to him. "Congrats on the sale," DPR wrote, initiating an exchange in which he later referenced his girlfriend. Curious about how DPR managed his double life, the seller asked, "Does she know who you are? . . . Dread, I mean."
"No way," DPR replied. "Maybe never."
"How can you hide that from her? I have to guess that [you are] spending at least 10 to 12 hours a day on SR."
"I've become good at hiding," DPR replied.
On January 17th, 2013, a postal worker delivered Green his package, which he opened to find 1,092 grams of coke inside. But he never had the chance to pass it along to his buyer. The postal worker was, in fact, an undercover agent, and Green was immediately arrested. Though it's unclear how much DPR knew about the bust, he trusted the seller enough to confide in him about the arrest. He also claimed that Green had stolen $350,000 in Bitcoins from Silk Road vendors, whom DPR now had to pay back.
"I'd like him beat up, then forced to send the Bitcoins he stole back," DPR wrote. The seller agreed to send thugs to take care of this for DPR. As he explained to the seller the next day, DPR feared that Green "was on the inside for a while, and now that he's been arrested, I'm afraid he'll give up info." This called for heavier means. "Can you change the order to execute rather than torture?" DPR wrote. He had "never killed a man or had one killed before," he added, "but it is the right move in this case."
DPR agreed to pay the seller $80,000, promising half up front and half when the job was done. According to prosecutors, DPR arranged for $40,000 to be wired from Australia in early February, saying that before sending the rest, he needed "proof of death," as he put it. "Ask for a video, if they can't do that, then pictures. . . . I'm more concerned about silencing him than getting the money back. . . . I have to assume he will sing."
On February 12th, DPR logged online and got the word. The plan was in action. Green "is still alive but being tortured," the seller wrote. The killers "are good; they should break him."
"Shouldn't be hard," DPR typed back.
But DPR's bluster seemed to waver when the seller sent him pictures of Green being tortured. He was "a little disturbed, but I'm OK," he wrote. "I'm new to this. . . . I don't think I've done the wrong thing. . . . I'm sure I will call on you again at some point, though I hope I won't have to." When the next photo came, on February 21st, it showed Green, dead from asphyxiation, his pale, heavy body lifeless and inert. "I'm pissed I had to kill him, but what's done is done," the seller wrote. DPR replied, "I just can't believe he was so stupid. . . . I just wish more people had some integrity."
After spending several months in Australia and a short stint back in Austin, Ulbricht had moved to San Francisco on the suggestion of his childhood friend René Pinnell, who offered him a job and a place to stay. Ulbricht, still a seeker at heart, agreed. "It seemed cosmic," he later recalled, "and the thing to do."
Ulbricht quickly fell for the town. "The crazy thing about San Francisco," he told Pinnell in an interview the two recorded for StoryCorps, "is it feels like home already." In public, Ulbricht seemed like his old carefree self. He hit up the local parties, went camping in the mountains and played Frisbee. "Paradise is here or nowhere," he posted on Facebook.
But around this time, Dread Pirate Roberts was posting on Silk Road that he felt lonely and isolated. "I have no one to share my thoughts with in physical space," he lamented. "Security does not permit it, so thanks for listening." The challenges to Ulbricht's alleged alter ego, DPR, were mounting, and the business was growing rougher. New black-market sites – such as Atlantis, Sheep Marketplace and Black Market Reloaded – were moving in on his turf. When Silk Road went offline for nearly a week after a hacking attack in April 2013, concern rose that it had been the work of its competitors.
DPR had even more problems. According to messages seized by the FBI, a Silk Road user nicknamed FriendlyChemist was demanding $500,000, which he needed to pay off his drug suppliers, or he would divulge a trove of personal data hacked from the site's online community. To prove he wasn't bluffing, FriendlyChemist sent DPR some samples of the personal data he was prepared to leak.
"Have your suppliers contact me here, so I can work something out with them," DPR replied. A few days later, DPR heard from another Silk Road user, Redandwhite – the well-known alias for the Hells Angels. "We are the people FriendlyChemist owes money to . . . ," Redandwhite messaged. "What do you want to talk to us about?" Apparently recognizing the value of Redandwhite's connections, DPR made a pitch. "FriendlyChemist aside," DPR wrote, "we have access to illicit substances in quantity and are having issues with bad distributors. If you don't already sell here on Silk Road, I'd like you to consider becoming a vendor."
"If you can get FriendlyChemist to meet up with us, or pay us his debt, then I'm sure I would be able to get people in our group to give this online side of the business a try," Redandwhite replied. DPR proposed a deal. FriendlyChemist, he wrote, "is a liability and I wouldn't mind if he was executed. . . . I have the following info and am waiting on getting his address."
After FriendlyChemist ramped up his threat two days later, demanding the $500,000 within 72 hours, DPR messaged Redandwhite, saying FriendlyChemist was "causing me problems. . . . I would like to put a bounty on his head, if it's not too much trouble for you." The next day, he wrote him again: "This kind of behavior is unforgivable to me. Especially here on Silk Road, anonymity is sacrosanct." The murder, he added, "doesn't have to be clean."
Redandwhite told him the killing would cost between $150,000 and $300,000, "depending on how you want it done." DPR balked. "Don't want to be a pain here, but the price seems high," he replied. "Not long ago, I had a clean hit done for $80K. Are the prices you quoted the best you can do?" They finally settled on 1,670 Bitcoins – roughly $150,000 – which DPR promptly sent. "I received the payment," Redandwhite replied. DPR handed over the real name of FriendlyChemist and said he lived in White Rock, British Columbia, with his wife and three kids. "We know where he is," Redandwhite said. "He'll be grabbed tonight. I'll update you."
Twenty-four hours later, the job was done. "Your problem has been taken care of . . . ," Redandwhite messaged DPR. "Rest easy though, because he won't be blackmailing anyone again. Ever." He included a picture that showed the corpse, which had a piece of paper near it with a series of numbers that DPR had instructed him to write for added veracity. "I've received the picture and deleted it," DPR replied. "Thank you again for your swift action."
At this point, Redandwhite said that before killing FriendlyChemist, the hitmen made sure "he spilled everything," including the location of another Silk Road user, Tony76, who lived in Surrey, British Columbia, and had been conspiring with him "on this scheme to blackmail you." Tony76 was a drug dealer who lived and worked with three others, Redandwhite had learned. After some more back-and-forth, DPR agreed to pay Redandwhite $500,000 to kill Tony76 and his three roommates. Then he transferred the Bitcoins to Redandwhite.
The next week, on April 15th, 2013, Redandwhite sent DPR a message telling him "that problem was dealt with. I'll try to catch you online to give you details. Just wanted to let you know right away so you have one less thing to worry about."
"Thanks," DPR replied.
By summer 2013, the feds seemed to be closing in on Silk Road. In May, a 14-year-old boy was busted in Fishers, Indiana, for buying Ecstasy on the site. In June, news broke that the U.S. Drug Enforcement Administration had seized $814 in Bitcoins – the first such seizure of digital currency – from a 31-year-old Charleston man for allegedly dealing on Silk Road under the name Casey Jones.
In late July, the FBI's cybercrime team had enough to access one of Silk Road's secret servers in an undisclosed country. They obtained data going back to 2011, including more than 1.2 million financial transactions. In the course of their investigation, they would also uncover an archive of DPR's e-mails, including his correspondence with Redandwhite and requests by DPR to buy fake IDs, which he said he needed to rent more servers under assumed names.
On July 26th, there was a knock at Ulbricht's door. Ulbricht had recently moved to an apartment on 15th Avenue in San Francisco. For $1,200 a month, the sublet, which he shared with two roommates, was a modest place on a picturesque street. If Ulbricht's roommates heard the men at the door ask for Ulbricht by name, however, they would have been surprised. They only knew him as Joshua Terrey. "Josh" had answered their Craigslist ad in June, describing himself in his e-mail as a "29 yo Texan man, good natured and clean/tidy." He said he was a currency trader who did freelance IT work and that he was new to the area and didn't have a cellphone yet. "Would you mind if I paid in cash?" he'd asked.
But it seemed that Josh wasn't Ulbricht's only alias. The men at the door were federal agents, and they had come to investigate a package of nine phony driver's licenses that had been intercepted at the Canadian border and sent to this address. One of the agents handed Ulbricht a California driver's license that bore his picture but a different name: Sean David Lake. Ulbricht showed them his Texas license but refused to entertain their questions, other than saying that "hypothetically," anyone could buy fake IDs on a site called Silk Road.
Though it's unclear why Ulbricht namechecked the site, the agents left without incident. But in an August 2013 interview with Forbes over an encrypted chat, DPR said he was feeling the heat. "The highest levels of government are hunting me," he typed from an undisclosed location. "I can't take any chances."
In early September, Ulbricht was with his family at a home they had rented in San Francisco's Noe Valley. His sister was in town for a wedding, so they had decided to make it a family get-together. Ulbricht's parents drove up from Austin. Ulbricht seemed in good spirits and made no mention of the visit by the federal agents. "It was just fun," his dad, Kirk, recalls, "and great to be all together again." His sister, Cally, says, "Ross seemed really relaxed and really comfortable."
Two weeks later, Lyn and Kirk were back in Austin when their phone rang. Lyn watched Kirk's face drop. "Oh, my God," he said. He turned to his wife and told her, "Ross has been arrested."
When Ulbricht was apprehended at the Glen Park library, the feds claimed to have caught him red-handed. Prosecutors say his laptop showed he was logged on to a Silk Road administration panel listing messages from customers needing his attention. He was also allegedly logged on to a Silk Road page titled "Mastermind."
The feds say that despite his tech savvy, Ulbricht had left loose ends, exposing, via an alias, his e-mail address when soliciting a developer to join a Bitcoin startup. Files allegedly found on Ulbricht's laptop were even more damning. There was the private log detailing DPR's murder-for-hire plots involving Redandwhite, who has not yet been publicly identified or charged. The Redandwhite hits remain a mystery; Canadian authorities found no reports of homicides in the area that matched the supposed victims, and the whole thing may well have been an elaborate con. As for the hit DPR ordered on Green, it was actually a sting operation involving an undercover agent, and the murder was staged with Green's cooperation. But whatever the outcomes, prosecutors say that "Ulbricht clearly intended for these killings to happen."
The feds also say they discovered research Ulbricht had conducted to flee the country and to obtain citizenship in the Caribbean. A file labeled "emergency" detailed his escape plan if caught: "Encrypt and backup important files on laptop to memory stick. Destroy laptop, destroy phone, hide memory stick, get new laptop, go to end of train, find place to live on Craigslist for cash, create new identity (name, backstory)." As the prosecutors put it, "He had contemplated and prepared for a life on the run." They also seized money from Ulbricht's computer – roughly $30 million in Bitcoins – with more, perhaps, out there to be found.
Since his arrest, Ulbricht's loved ones have struggled to make sense of the allegations. "It's like hearing that your grandmother was accused of this stuff," says his friend Schiller. "It just doesn't add up." None are more flummoxed than Ulbricht's family. "I would stake my life that he's not a murderer," Lyn says. "This is way beyond something he could ever be capable of," says Kirk. "I believe they got the wrong guy."
Raising legal-defense money through their site, Freeross.org, the family has hired a high-powered lawyer to handle the case: Joshua Dratel, who, having defended Al Qaeda operatives and a Guantánamo Bay inmate, has experience with controversial clients. Though Ulbricht filed a claim requesting the return of the Bitcoins seized by the government from his computer, stating that he "has an interest as owner," Dratel has said that "the evidence will establish that he's not the person who the government says he is." As for the tens of millions on Silk Road's servers, a federal judge ordered it all to be forfeited in January.
As the federal case against him unfolds, Ulbricht is biding his time playing ping-pong, teaching yoga and reading at the Metropolitan Detention Center in Brooklyn, where he is denied Internet access. But the Silk Road fallout continues. Dealers and buyers have been arrested around the world for using the site, and federal scrutiny into the online illegal-drug market has never been higher.
Still, other black-market sites have attempted to capitalize on Silk Road's abandoned community, among them a revamped version of Silk Road, whose administrator has adopted the moniker Dread Pirate Roberts and sounds a lot like his martyred predecessor. "You don't need drugs to care about privacy," he recently tweeted. "We are freedom fighters."
Ulbricht has been thinking about his own legacy. In the StoryCorps interview, Pinnell asked him where he saw himself in 20 years. "I want to have had a substantial positive impact on the future of humanity by that time," Ulbricht said. But it didn't end there. When Pinnell asked, "Do you think you're going to live forever?" a smile spread across Ulbricht's face. "I think there's a possibility," he replied.
This story is from the February 13th, 2014 issue of Rolling Stone.
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