by Yasha Levine
He began to prepare. In 2012, he relocated to another NSA assignment for Dell, this time in Hawaii. There, working for the NSA’s information-sharing office out of an underground bunker once used as a storage facility, Snowden began collecting the documents he would use to expose America’s surveillance apparatus. He even applied for a transfer to a different NSA division—this one under contractor Booz Allen Hamilton—because it would give him access to a set of documents on US cyberwar operations that he thought the American people should see.46 “My position with Booz Allen Hamilton granted me access to lists of machines all over the world the NSA hacked. That is why I accepted that position about three months ago,” he told the South China Morning Post from his hideout in Hong Kong.47
Snowden explained his motive in simple moral terms. It was something that many could relate to, and he soon emerged as a global cult icon who cut through left and right political divides. To Michael Moore, he was the “hero of the year.” To Glenn Beck, he was a patriotic leaker—courageous and not afraid to accept the consequences.48 Even fellow NSA whistle-blowers were impressed. “I’ve never run across anyone quite like Snowden. He is a uniquely postmodern breed of whistle-blower,” wrote James Bamford.49 But for all the praise he received, this modern-day Daniel Ellsberg cut a peculiar political profile.
Edward Snowden eventually escaped to Russia, the only country that could guarantee his safety from the long arm of the United States. There, while living under state protection at an undisclosed location in Moscow, he swept Silicon Valley’s role in Internet surveillance under the rug. Asked about it by Washington Post reporter Barton Gellman, who had first reported on the NSA’s PRISM program, Snowden shrugged off the danger posed by companies like Google and Facebook. The reason? Because private companies do not have the power to arrest, jail, or kill people. “Twitter doesn’t put warheads on foreheads,” he joked.50
For someone who spent years cycling through the CIA and NSA, enjoying access to the deepest secrets of America’s surveillance state, Snowden’s views were curiously simple and naive. He seemed ignorant of the deep historical ties between technology companies and the US military. Indeed, he seemed ignorant about key aspects of the very documents he had lifted from the NSA, which showed just how integral data produced by consumer technology companies were to deadly government operations abroad. That included the CIA’s global drone assassination program, which depended on the NSA tracking cellphones to Al-Qaeda operatives in Pakistan and Yemen, and then using that geolocation data to carry out missiles strikes.51 Even General Michael Hayden, former director of the CIA and NSA, admitted that data taken from commercial technologies are used for strikes and hits. “We kill people based on metadata,” he said during a debate at Johns Hopkins University.52 In other words, Snowden’s NSA documents proved the exact opposite of what Snowden was arguing. Wittingly or unwittingly, whether for good or ill, personal information generated by private companies—companies like Twitter, Google, and telecoms in Pakistan—did in fact help put warheads on foreheads.
Snowden’s views on private surveillance were simplistic, but they seemed to be in line with his politics. He was a libertarian and believed the utopian promise of computer networks. He believed that the Internet was an inherently liberating technology that, if left alone, would evolve into a force of good in the world. The problem wasn’t Silicon Valley; it was government power. To him, cynical intelligence agencies like the NSA had warped the utopian promise of the Internet, turning it into a dystopia where spies tracked our every move and recorded everything we said. He believed the government was the central problem and distrusted legislative or political solutions to curb surveillance, which would only involve the government even more. As it so happened, his line of thinking tracked perfectly with the antigovernment privacy initiatives that Internet companies like Google and Facebook had started pushing to deflect attention from their private surveillance practices.
“We need ways of engaging in private communications. We need mechanisms affording for private associations. And ultimately, we need ways to engage in private payment and shipping, which are the basis of trade,” Snowden explained to Micah Lee in a posh Moscow hotel near Red Square. Lee was a former technologist with the EFF who, from his home in Berkeley, California, had worked in secret to help Snowden securely communicate with journalists and carry out his leaks. He’d trekked to Moscow to talk to Snowden face to face about what people could do to “reclaim their privacy.”
“I think reform comes with many faces,” Snowden told Lee. “That can be through technology, that can be through politics, that can be through voting, that can be through behavior. But technology is… perhaps the quickest and most promising means through which we can respond to the greatest violations of human rights in a manner that is not dependent on every single legislative body on the planet to reform itself at the same time, which is probably somewhat optimistic to hope for. We would be instead able to create systems… that enforce and guarantee the rights that are necessary to maintain a free and open society.”53
To Snowden, the Internet was broken, but all was not lost. Laws, regulations, rules—in the long run none of these would do any good. The only truly permanent solution was technology.
What kind of technology? The Tor Project.
End of Government
In 2011, a mysterious store appeared on the Internet. Called Silk Road, it was an online store like any other, complete with customer reviews and a merchant rating system. But there was also something unique about this marketplace: it sold illegal drugs and was only accessible through a network called Tor, a novel Internet system that supposedly made the store and its users impervious to the law by moving all transactions onto a parallel anonymous network that sat atop the real Internet. Tor is what’s now known as the “dark web.”
“Making small talk with your pot dealer sucks. Buying cocaine can get you shot. What if you could buy and sell drugs online like books or light bulbs? Now you can: Welcome to Silk Road,” wrote Adrian Chen, the reporter who broke the story for Gawker. “Through a combination of anonymity technology and a sophisticated user-feedback system, Silk Road makes buying and selling illegal drugs as easy as buying used electronics—and seemingly as safe. It’s Amazon—if Amazon sold mind-altering chemicals.”54
Built and operated by a mysterious figure who went by the name of Dread Pirate Roberts, Silk Road had two components that allowed it to operate in total anonymity. One, all purchases were processed using a new digital crypto-currency called Bitcoin, which was created by the mysterious pseudonymous cryptographer Satoshi Nakamoto. Two, to use Silk Road, both buyers and sellers first had to download a program called Tor and use a specialized browser to access a specialized store URL—http://silkroad6ownowfk.onion—that took them off the Internet and into the Tor cloud, a.k.a. the dark web.
Tor was a cutting-edge anonymity tool made by Tor Project, a nonprofit set up in 2004 by a plump and ponytailed cryptographer named Roger Dingledine, who at the time ran it out of a cluttered office above a YMCA in Cambridge, Massachusetts. It had about a $2 million annual budget, a half dozen full-time employees, and a small group of dedicated volunteer coders around the world who helped develop, test, and release its product: a free cloaking app that worked on the basis of a technique called “onion routing.” Users downloaded and launched a specialized Tor Internet browser that redirected their traffic onto a parallel volunteer peer-to-peer network, bouncing it around randomly before sending it off to its final destination. This trick disconnected the origin and destination of a person’s Internet browsing stream and theoretically made it impossible for cops, spies, hackers, or anyone else monitoring Internet traffic to observe where users were coming from and where they were going. In lay terms, onion routing is like a street hustler playing a shell game with network traffic: people can see it go under one of the shells, but they never know where it ends up. Tor powered the bulk of the dark web. Tor pretty much was the dark web.
Thanks to
Tor, Silk Road ran without a hitch. It developed a mass following and built a booming drug dealer community, like eBay did for amateur collectors. Former small-time drug dealers moved their operations online and expanded their client bases, which were no longer limited to personal connections and neighborhoods. Meanwhile, cops logged into Silk Road through Tor like anyone else and clicked through offerings of PCP, LSD, MDMA, cocaine, crystal meth, and ketamine and read customer reviews, but they didn’t have a clue about the real-world identity of the people selling and buying the drugs; nor could they know where to serve their arrest warrants or which datacenters to raid. Everyone was anonymous and was trading anonymous cash. And Silk Road itself ran as a Tor “hidden service,” which meant that it could be hosted in San Francisco or across the globe in Moscow. The only thing not anonymous was that the drugs had to be shipped, so drug sellers developed routines where they would drive for hours to neighboring cities to ship the goods; they never shipped from one location two times in a row. The FBI and Drug Enforcement Agency watched as kids bought and sold drugs in plain sight, while the Dread Pirate Roberts raked in an estimated $32 million a year in commissions, but they couldn’t do anything to stop it.55 Thanks to Tor, everyone was anonymous and safe. That’s how powerful the technology was supposed to be. It seemed like magic.
Tor was the realization of a dream decades in the making.
Since the early 1990s, an influential group of programmers and hackers calling themselves “cypherpunks” had pursued a radical political idea. They believed that powerful encryption and anonymity technology, combined with untraceable digital currencies, would bring a revolution that swept away government power and established a decentralized global world order based on free markets and voluntary association.56 “The State will of course try to slow or halt the spread of this technology, citing national security concerns, use of the technology by drug dealers and tax evaders, and fears of societal disintegration. Many of these concerns will be valid; crypto anarchy will allow national secrets to be traded freely and will allow illicit and stolen materials to be traded. An anonymous computerized market will even make possible abhorrent markets for assassinations and extortion,” predicted Timothy May, a bearded, pioneering engineer at Intel and one of the key founders of the cypherpunk movement, back in 1992. May proselytized his ideas with a messianic zeal. By 1994, he was predicting that a global cryptorevolution was just around the corner and that it would create a new world free of governments and centralized control. “A phase change is coming,” he wrote, echoing the prediction that Louis Rossetto was making at the same time in the pages of Wired magazine, which itself was a promoter of the cypherpunk movement and his ideas.57
The cypherpunk vision of the future was an inverted version of the military’s cybernetic dream pursued by the Pentagon and Silicon Valley: instead of leveraging global computer systems to make the world transparent and predictable, cypherpunks wanted to use computers and cryptography to make the world opaque and untrackable. It was a counterforce, a cybernetic weapon of individual privacy and freedom against a cybernetic weapon of government surveillance and control.
Tor offered a realization of this cypher-cybernetic dream: total anonymity on the Internet. Starting in the mid-2000s, Tor developed a cult following among a small but influential group of techno-libertarians, hackers, and cypherpunks who saw it as a magic cloak that could render the government—cops, militaries, tax collectors, regulators, and spies—powerless.
The mysterious creator of the Silk Road, the Dread Pirate Roberts, adhered to the cypherpunk ideology. He believed in the liberatory promise of Tor and cryptography. In his public statements, Dread Pirate Roberts came off as a typical libertarian, not much different from Edward Snowden. He followed Austrian Economics, argued against environmental regulations and child labor laws, praised sweatshops, and mocked the need for minimum wage: “How about someone whose labor is worth less than minimum wage?” As for Silk Road, it was much more than a business. From his hideout somewhere in the dark web, Dread Pirate Roberts saw it as a revolutionary act straight out of an Ayn Rand novel. Government was the ultimate political evil—a parasite, a form of slavery. Tor was the weapon that let a little guy like him fight back. Silk Road was just the beginning. He wanted to use Tor and other crypto tools to scale up the experiment to encompass all parts of life, not just drug purchases.
“What if one day we had enough power to maintain a physical presence on the globe, where we shunned the parasites and upheld the rule of law, where the right to privacy and property was unquestioned and enshrined in the very structure of society. Where police are our servants and protectors beholden to their customers, the people. Where our leaders earn their power and responsibility in the harsh and unforgiving furnace of the free market and not from behind a gun, where the opportunities to create and enjoy wealth are as boundless as one’s imagination,” he wrote to users of Silk Road on the site’s messaging board. “Once you’ve seen what’s possible, how can you do otherwise? How can you plug yourself into the tax eating, life sucking, violent, sadistic, war mongering, oppressive machine ever again? How can you kneel when you’ve felt the power of your own legs? Felt them stretch and flex as you learn to walk and think as a free person? I would rather live my life in rags now than in golden chains. And now we can have both! Now it is profitable to throw off one’s chains, with amazing crypto technology reducing the risk of doing so dramatically. How many niches have yet to be filled in the world of anonymous online markets? The opportunity to prosper and take part in a revolution of epic proportions is at our fingertips!”58
And why not? If Silk Road could withstand the power of the American government, anything seemed possible.
More practically, the Dread Pirate Roberts proved that you could use Tor to run a massively illegal business on the Internet and keep law enforcement at bay, while raking in millions. His success spawned a mass of copycats—dark web entrepreneurs who set up online stores in Silk Road’s image, allowing people to anonymously buy whatever they wanted: weed, marijuana, ecstasy, cocaine, meth, guns, grenades, and even assassinations.59 Some of the sites were possibly a racket, meant to bilk people of their Bitcoins, but others appeared dead serious. Tor’s dark web became a haven for child abuse pornography, allowing forums and markets where such material was swapped and sold to exist beyond the reach of law enforcement. It also housed websites operated by terrorist cells, including recruitment platforms run by the Islamic State of Iraq and the Levant.60
Tor’s ease of use and bullet-proof anonymity didn’t just empower the seedy side of the Internet. Journalists and political activists used it to avoid government surveillance and repression in countries like China and Iran. Leakers and whistle-blowers used the network, too. That’s where Edward Snowden came into the story: Tor’s ability to hide people from the prying eyes of the NSA was a key factor in his leaks; he couldn’t have carried them out successfully without it.
Snowden Tor
Edward Snowden was a huge fan of the Tor Project. He, like the Dread Pirate Roberts, believed in the power of cryptography to liberate the Internet from government control. In Hawaii, when he had worked as an NSA contractor at Dell and the Silk Road was booming, he controlled one of the most powerful nodes on the Tor network, running a physical server that helped mix and anonymize traffic. He also took it upon himself to educate people in Hawaii about how to use the Tor network to hide from the government.
In November 2012, while in the middle of exfiltrating documents, Snowden reached out to Runa Sandvik, a Tor employee, and asked for some Tor stickers to hand out to his buddies at work.61 He did not tell her that his “work” was for the NSA. But in the course of their back-and-forth, he found out that Sandvik was planning to visit Hawaii for vacation, and she suggested they meet up there. In her capacity as a Tor ambassador, Sandvik offered to give a talk for locals about communication security and encryption. Snowden was enthusiastic about the idea, and they agreed to cohost a “crypto party,” a kin
d of public teach-in about encryption tools. The event went down in early December 2012 at an art space in Honolulu, where Snowden and Sandvik taught about twenty people how to use Tor and encrypt their hard drives. Snowden personally hosted a session about how to set up and run a Tor server.62
Snowden hooking up with Tor employees, running Tor servers, and hosting Tor training sessions—all while planning the biggest heist of NSA documents in history? It seemed to be a reckless step for someone as meticulous as he was. Why would he risk outing himself? To those in the privacy world, Snowden’s desire to educate people about privacy, even in the face of personal danger, was a testament to his belief in the power of Tor and cryptography and his dedication to the cause. “That Snowden organized such an event himself while still an NSA contract worker speaks volumes about his motives,” wrote Wired reporter Kevin Poulsen, who broke the story about Snowden’s Tor server and crypto party.
But Snowden wasn’t just a true believer. He was also an active user.
After fleeing to Moscow, he explained that the Tor Project was vital to carrying out his mission. He had relied on Tor to cover his tracks and avoid detection while communicating with journalists, transferring documents, and planning his escape from Hawaii. He was such a fan that the first photographs of him in Hong Kong showed him sitting on his hotel bed, a black laptop with a giant green oval “Tor Project” sticker plastered on its cover perched on his lap. “I think Tor is the most important privacy-enhancing technology project being used today. I use Tor personally all the time,” he said in an interview from Moscow.