by Yasha Levine
With those words, Appelbaum and the Tor Project became central heroes in the WikiLeaks saga, right behind Assange. Appelbaum leveraged his new rebel status for all it was worth. He regaled reporters with wild stories of how his association with WikiLeaks made him a wanted man. He talked about being pursued, interrogated, and threatened by shadowy government forces. He described in chilling detail how he and everyone he knew were thrown into a nightmare world of Big Brother harassment and surveillance. He claimed his mother was targeted. His girlfriend received nightly visits by men clad in black. “I was in Iceland working with a friend about their constitution’s reform. And she saw two men outside of her house on the ground floor in her backyard, meaning that they were on her property inside of a fence. And they—one of them was wearing night vision goggles and watching her sleep,” he recounted in a radio interview. “So she just laid in bed in pure terror for the period of time in which they stood there and watched her. And presumably, this is because there was a third person in the house placing a bug or doing something else, and they were keeping watch on her to make sure that if she were to hear something or to get up, they would be able to alert this other person.”84
He was a great performer and had a knack for giving journalists what they wanted. He spun fantastic stories, and Tor was at the center of them all. Reporters lapped it up. The more exaggerated and heroic his performance, the more attention flowed his way. News articles, radio shows, television appearances, and magazine spreads. The media couldn’t get enough.
In December 2010, Rolling Stone published a profile of Appelbaum as “the Most Dangerous Man in Cyberspace.” The article portrayed him as a fearless techno-anarchist warrior who had dedicated his life to taking down America’s evil military-surveillance apparatus, no matter the cost to his own life. It was full of high drama, chronicling Appelbaum’s life on the post-WikiLeaks run. Descriptions of barren hideout apartments, Ziploc bags filled with cash from exotic locations, and photos of scantily clad punk girls—presumably Appelbaum’s many love interests. “Appelbaum has been off the grid ever since—avoiding airports, friends, strangers and unsecure locations, traveling through the country by car. He’s spent the past five years of his life working to protect activists around the world from repressive governments. Now he is on the run from his own,” wrote Rolling Stone reporter Nathaniel Rich.85
His association with WikiLeaks and Assange boosted the Tor Project’s public profile and radical credentials. Support and accolades poured in from journalists, privacy organizations, and government watchdogs. The American Civil Liberties Union partnered with Appelbaum on an Internet privacy project, and New York’s Whitney Museum—one of the leading modern art museums in the world—invited him for a “Surveillance Teach-In.”86 The Electronic Frontier Foundation gave Tor its Pioneer Award, and Roger Dingledine made it on Foreign Policy magazine’s list of Top 100 Global Thinkers for protecting “anyone and everyone from the dangers of Big Brother.”87
As for Tor’s deep, ongoing ties to the US government? Well, what of them? To any doubters, Jacob Appelbaum was held up as living, breathing proof of the radical independence of the Tor Project. “If the users or developers he meets worry that Tor’s government funding compromises its ideals, there’s no one better than Appelbaum to show the group doesn’t take orders from the feds,” wrote journalist Andy Greenberg in This Machine Kills Secrets, a book about WikiLeaks. “Appelbaum’s best evidence of Tor’s purity from Big Brother’s interference, perhaps, is his very public association with WikiLeaks, the American government’s least favorite website.”
With Julian Assange endorsing Tor, reporters assumed that the US government saw the anonymity nonprofit as a threat. But internal documents obtained through FOIA from the Broadcasting Board of Governors, as well as an analysis of Tor’s government contracts, paint a different picture. They reveal that Appelbaum and Dingledine worked with Assange on securing WikiLeaks with Tor since late 2008 and that they kept their handlers at the BBG informed about their relationship and even provided information about the inner workings of WikiLeaks’s secure submissions system.
“Talked to the WikiLeaks people (Daniel and Julian) about their use of Tor hidden services, and how we can make things better for them,” Dingledine wrote in a progress report he sent to the BBG in January 2008. “It turns out they use the hidden service entirely as a way to keep users from screwing up—either it works and they know they’re safe or it fails, but either way they don’t reveal what they’re trying to leak locally. So I’d like to add a new ‘secure service’ feature that’s just like a hidden service but it only makes one hop from the server side rather than three. A more radical design would be for the ‘intro point’ to be the service itself, so it really would be like an exit enclave.”88 In another progress report sent to the BBG two years later, in February 2010, Dingledine wrote, “Jacob and WikiLeaks people met with policymakers in Iceland to discuss freedom of speech, freedom of press, and that online privacy should be a fundamental right.”
No one at the BBG raised any objections. To the contrary, they appeared to be supportive. We do not know if anyone at the BBG forwarded this information to some other government body, but it would not be hard to imagine that information about WikiLeaks’ security infrastructure and submission system was of great interest to US intelligence agencies.
Perhaps most telling was that support from the BBG continued even after WikiLeaks began publishing classified government information and Appelbaum became the target of a larger Department of Justice investigation into WikiLeaks. For example, on July 31, 2010, CNET reported that Appelbaum had been detained at the Las Vegas airport and questioned about his relationship with WikiLeaks.89 News of the detention made headlines around the world, once again highlighting Appelbaum’s close ties to Julian Assange. And a week later, Tor’s executive director Andrew Lewman, clearly worried that this might affect Tor’s funding, emailed Ken Berman at the BBG in the hopes of smoothing things over and answering “any questions you may have about the recent press regarding Jake and WikiLeaks.” But Lewman was in for a pleasant surprise: Roger Dingledine had been keeping the folks at the BBG in the loop, and everything seemed to be okay. “Great stuff, thx. Roger answered a number of questions when he met us this week in DC,” Berman replied.90
Unfortunately, Berman didn’t explain in the email what he and Dingledine discussed about Appelbaum and WikiLeaks during their meeting. What we do know is that Tor’s association with WikiLeaks produced no real negative impact on Tor’s government contracts.91
Its 2011 contracts came in without a hitch—$150,000 from the Broadcasting Board of Governors and $227,118 from the State Department.92 Tor was even able to snag a big chunk of money from the Pentagon: a new $503,706 annual contract from the Space and Naval Warfare Systems Command, an elite information and intelligence unit that houses a top-secret cyber-warfare division.93 The navy contract was passed through SRI, the old Stanford military contractor that had done counterinsurgency, networking, and chemical weapons work for ARPA back in the 1960s and 1970s. The funds were part of a larger navy “Command, Control, Communications, Computers, Intelligence, Surveillance, and Reconnaissance” program to improve military operations. A year later, Tor would see its government contracts more than double to $2.2 million: $353,000 from the State Department, $876,099 from the US Navy, and $937,800 from the Broadcasting Board of Governors.94
When I crunched the numbers, I couldn’t help but do a double take. It was incredible. WikiLeaks had scored a direct hit on Tor’s government backers, including the Pentagon and State Department. Yet Appelbaum’s close partnership with Assange produced no discernable downside.
I guess it makes sense, in a way. WikiLeaks might have embarrassed some parts of the US government, but it also gave America’s premier Internet Freedom weapon a major injection of credibility, enhancing its effectiveness and usefulness. It was an opportunity.
Social Media as a Weapon
In 2011, less than a ye
ar after WikiLeaks broke onto the world stage, the Middle East and North Africa exploded like a powder keg. Seemingly out of nowhere, huge demonstrations and protests swept through the region. It started in Tunisia, where a poor fruit seller lit himself on fire to protest humiliating harassment and extortion at the hands of the local police. He died from his burns on January 4, triggering a national protest movement against Tunisia’s dictatorial president, Zine El Abidine Ben Ali, who had ruled the country for twenty-three years. Within weeks, massive antigovernment protests spread to Egypt, Algeria, Oman, Jordan, Libya, and Syria.
The Arab Spring had arrived.
In Tunisia and Egypt, these protest movements toppled longstanding dictatorships from within. In Libya, opposition forces deposed and savagely killed Muammar Gaddafi, knifing him in the anus, after an extensive bombing campaign from NATO forces. In Syria, protests were met with a brutal crackdown from Bashar Assad’s government, and led to a protracted war that would claim hundreds of thousands of lives and trigger the worst refugee crisis in recent history, pulling in Saudi Arabia, Turkey, Israel, the CIA, the Russian Air Force and special operations teams, Al-Qaeda, and ISIL. Arab Spring turned into a long, bloody winter.
The underlying causes of these opposition movements were deep, complex, and varied from country to country. Youth unemployment, corruption, drought and related high food prices, political repression, economic stagnation, and longstanding geopolitical aspirations were just a few of the factors. To a young and digitally savvy crop of State Department officials and foreign policy planners, these political movements had one thing in common: they arose because of the democratizing power of the Internet. They saw social media sites like Facebook, Twitter, and YouTube as democratic multipliers that allowed people to get around official state-controlled information sources and organize political movements quickly and efficiently.
“The Che Guevara of the 21st Century is the network,” Alec Ross, a State Department official in charge of digital policy under Secretary of State Hillary Clinton, gushed in the NATO Review, the official magazine of the North Atlantic Treaty Organization.95 His Che reference smacks of hypocrisy or perhaps ignorance; Che, after all, was executed by Bolivian forces backed by the United States, in particular, by the CIA.
The idea that social media could be weaponized against countries and governments deemed hostile to US interests wasn’t a surprise. For years the State Department, in partnership with the Broadcasting Board of Governors and companies like Facebook and Google, had worked to train activists from around the world on how to use Internet tools and social media to organize opposition political movements. Countries in Asia, the Middle East, and Latin America as well as former Soviet states like the Ukraine and Belarus were all on the list. Indeed, the New York Times reported that many of the activists who played leading roles in the Arab Spring—from Egypt to Syria to Yemen—had taken part in these training sessions.96
“The money spent on these programs was minute compared with efforts led by the Pentagon,” reported the New York Times in April 2011. “But as American officials and others look back at the uprisings of the Arab Spring, they are seeing that the United States’ democracy-building campaigns played a bigger role in fomenting protests than was previously known, with key leaders of the movements having been trained by the Americans in campaigning, organizing through new media tools and monitoring elections.” The trainings were politically charged and were seen as a threat by Egypt, Yemen, and Bahrain—all of which lodged complaints with the State Department to stop meddling in their domestic affairs, and even barred US officials from entering their countries.97
An Egyptian youth political leader who attended State Department training sessions and then went on to lead protests in Cairo told the New York Times, “We learned how to organize and build coalitions. This certainly helped during the revolution.” A different youth activist, who had participated in Yemen’s uprising, was equally enthusiastic about the State Department social media training: “It helped me very much because I used to think that change only takes place by force and by weapons.”
Staff from the Tor Project played a role in some of these trainings, taking part in a series of Arab Blogger sessions in Yemen, Tunisia, Jordan, Lebanon, and Bahrain, where Jacob Appelbaum taught opposition activists how to use Tor to get around government censorship.98 “Today was fantastic… really a fantastic meeting of minds in the Arab world! It’s enlightening and humbling to have been invited. I really have to recommend visiting Beirut. Lebanon is an amazing place. Friendly people, good food, intense music, insane taxis,” Appelbaum tweeted after an Arab Bloggers training event in 2009, adding: “If you’d like to help Tor please sign up and help translate Tor software into Arabic.”99
Activists later put the skills taught at these training sessions to use during the Arab Spring, routing around Internet blocks that their governments threw up to prevent them from using social media to organize protests. “There would be no access to Twitter or Facebook in some of these places if you didn’t have Tor. All of the sudden, you had all these dissidents exploding under their noses, and then down the road you had a revolution,” Nasser Weddady, a prominent Arab Spring activist from Mauritania, later told Rolling Stone. Weddady, who had taken part in the Tor Project’s training sessions and who had translated a widely circulated guide on how to use the tool into Arabic, credited it with helping keep the Arab Spring uprisings alive. “Tor rendered the government’s efforts completely futile. They simply didn’t have the know-how to counter that move.”100
From a higher vantage point, the Tor Project was a wild success. It had matured into a powerful foreign policy tool—a soft-power cyber weapon with multiple uses and benefits. It hid spies and military agents on the Internet, enabling them to carry out their missions without leaving a trace. It was used by the US government as a persuasive regime-change weapon, a digital crowbar that prevented countries from exercising sovereign control over their own Internet infrastructure. Counterintuitively, Tor also emerged as a focal point for antigovernment privacy activists and organizations, a huge cultural success that made Tor that much more effective for its government backers by drawing fans and helping shield the project from scrutiny.
And Tor was just the beginning.
The Arab Spring provided the US government with the confirmation it was looking for. Social media, combined with technologies like Tor, could be tapped to bring huge masses of people onto the streets and could even trigger revolutions. Diplomats in Washington called it “democracy promotion.” Critics called it regime change.101 But it didn’t matter what you called it. The US government saw that it could leverage the Internet to sow discord and inflame political instability in countries it considered hostile to US interests. Good or bad, it could weaponize social media and use it for insurgency. And it wanted more.102
In the wake of the Arab Spring, the US government directed even more resources to Internet Freedom technologies. The plan was to go beyond the Tor Project and launch all sorts of crypto tools to leverage the power of social media to help foreign activists build political movements and organize protests: encrypted chat apps and ultrasecure operating systems designed to prevent governments from spying on activists, anonymous whistle-blowing platforms that could help expose government corruption, and wireless networks that could be deployed instantaneously anywhere in the world to keep activists connected even if their government turned off the Internet.103
Strangely enough, these efforts were about to get a major credibility boost from an unlikely source: an NSA contractor by the name of Edward Snowden.
Strange Alliances
The post-WikiLeaks years were good for the Tor Project. With the government contracts flowing, Roger Dingledine expanded the payroll, adding a dedicated crew of developers and managers who saw their job in messianic terms: to free the Internet of government surveillance.104
Jacob Appelbaum, too, was doing well. Claiming that harassment from the US government was too much to bea
r, he spent most of his time in Berlin in a sort of self-imposed exile. There, he continued to do the job Dingledine had hired him to do. He traveled the world training political activists and persuading techies and hackers to join up as Tor volunteers. He also did various side projects, some of which blurred the line between activism and intelligence gathering. In 2012, he made a trip to Burma, a longtime target of US government regime-change efforts.105 The purpose of the trip was to probe the country’s Internet system from within and collect information on its telecommunications infrastructure, information that was then used to compile a government report for policymakers and “international investors” interested in penetrating Burma’s recently deregulated telecom market.106
Appelbaum continued to draw a high five-figure salary from Tor, a government contractor funded almost exclusively by military and intelligence grants. But, to the public, he was a real-life superhero on the run from the US surveillance state—now hiding out in Berlin, the nerve center of the global hacker scene known for its nerdy mix of machismo, all-night hackathons, drug use, and partner swapping. He was a member of the Internet Freedom elite, championed by the American Civil Liberties Union and the Electronic Frontier Foundation, given a board seat on eBay founder Pierre Omidyar’s Freedom of the Press Foundation, and occupied an advisory role for London’s Centre for Investigative Journalism. His fame and rebel status only made his job as Tor’s pitchman more effective.
In Berlin, Appelbaum caught another lucky break for the Tor Project. In 2013, his good friend and sometimes-lover Laura Poitras, an American documentary filmmaker who also lived in the German capital in self-imposed exile, was contacted by a mysterious source who told her he had access to the crown jewels of the National Security Agency: documents that would blow America’s surveillance apparatus wide open.107 Poitras tapped Appelbaum’s knowledge of Internet systems to come up with a list of questions to vet the possible leaker and to make sure he really was the NSA technician he claimed to be. This source turned out to be Edward Snowden.108