Early one morning last December, Glenn Greenwald opened his laptop, scanned through his e-mail, and made a decision that almost cost him the story of his life. A columnist and blogger with a large and devoted following, Greenwald receives hundreds of e-mails every day, many from readers who claim to have “great stuff.” Occasionally these claims turn out to be credible; most of the time they’re cranks. There are some that seem promising but also require serious vetting. This takes time, and Greenwald, who starts each morning deluged with messages, has almost none. “My inbox is the enemy,” he told me recently.
And so it was that on December 1st, 2012, Greenwald received a note from a person asking for his public encryption, or PGP, key so he could send him an e-mail securely. Greenwald didn’t have one, which he now acknowledges was fairly inexcusable given that he wrote almost daily about national-security issues, and had likely been on the government’s radar for some time over his vocal support of Bradley Manning and WikiLeaks. “I didn’t really know what PGP was,” he admits. “I had no idea how to install it or how to use it.” It seemed time-consuming and complicated, and Greenwald, who was working on a book about how the media control political discourse, while also writing his column for The Guardian, had more pressing things to do.
“It felt Anonymous-ish to me,” Greenwald says. “It was this cryptic ‘I and others have things you would be interested in. . . .’ He never sent me neon lights – it was much more ambiguous than that.”
So he ignored the note. Soon after, the source sent Greenwald a step-by-step tutorial on encryption. Then he sent him a video Greenwald describes as “Encryption for Journalists,” which “walked me through the process like I was a complete idiot.”
And yet, Greenwald still didn’t bother learning security protocols. “The more he sent me, the more difficult it seemed,” he says. “I mean, now I had to watch a fucking video . . . ?” Greenwald still had no idea who the source was, nor what he wanted to say. “It was this Catch-22: Unless he tells me something motivating, I’m not going to drop what I’m doing, and from his side, unless I drop what I’m doing and get PGP, he can’t tell me anything.”
The dance went on for a month. Finally, after trying and failing to get Greenwald’s attention, the source gave up.
Greenwald went back to his book and his column, publishing, among other things, scathing attacks on the Obama administration’s Guantánamo and drone policies. It would take until May, six months after the anonymous stranger reached out, before Greenwald would hear from him again, through a friend, the documentarian Laura Poitras, whom the source had contacted, suggesting she and Greenwald form a partnership. In June, the three would meet face to face, in a Hong Kong hotel room, where Edward Snowden, the mysterious source, would hand over many thousands of top-secret documents: a mother lode laying bare the architecture of the national-security state. It was the “most serious compromise of classified information in the history of the U.S. intelligence community,” as former CIA deputy director Michael Morell said, exposing the seemingly limitless reach of the National Security Agency, and sparking a global debate on the use of surveillance – ostensibly to fight terrorism – versus the individual right to privacy. And its disclosure was also a triumph for Greenwald’s unique brand of journalism.
Greenwald is a former litigator whose messianic defense of civil liberties has made him a hero of left-libertarian circles, though he has alienated elites across the political spectrum. Famously combative, he “lives to piss people off,” as one colleague says. And in the past eight years he has done an excellent job: taking on Presidents Bush and Obama, Congress, the Democratic Party, the Tea Party, the Republicans, the “liberal establishment” and, notably, the mainstream media, which he accuses – often while being interviewed by those same mainstream, liberal-establishment journalists – of cozying up to power. “I crave the hatred of those people,” Greenwald says about the small, somewhat incestuous community of Beltway pundits, government officials, think-tank experts and other opinion-makers he targets routinely. “If you’re not provoking that reaction in people, you’re not provoking or challenging anyone, which means you’re pointless.”
This perspective has earned Greenwald tremendous support, especially among young, idealistic readers hungry for an uncompromised voice. “There are few writers out there who are as passionate about communicating uncomfortable truths,” Snowden, who was one of Greenwald’s longtime readers, tells me in an e-mail. “Glenn tells the truth no matter the cost, and that matters.”
The same, of course, could be said of Snowden, who, from the moment he revealed himself as the source of the leaks, has baffled the mainstream critics who’ve tried to make sense of him. “The founders did not create the United States so that some solitary 29-year-old could make unilateral decisions about what should be exposed,” wrote New York Times columnist David Brooks, who held up Snowden as one of “an apparently growing share of young men in their 20s who are living technological existences in the fuzzy land between their childhood institutions and adult family commitments.”
To the likes of Brooks, Snowden was a disconcerting mystery; Glenn Greenwald, though, got him right away. “He had no power, no prestige, he grew up in a lower-middle-class family, totally obscure, totally ordinary,” Greenwald says. “He didn’t even have a high school diploma. But he was going to change the world – and I knew that.” And, Greenwald also believed, so would he. “In all kinds of ways, my whole life has been in preparation for this moment,” he says.
For a man living in the middle of a John le Carré novel, Greenwald has a pretty good life. Based in Brazil since 2005, he lives about 10 minutes from the beach in the hills above Rio de Janeiro, in an airy, four-bedroom wood-and-glass house that backs directly into the jungle. There are monkeys, birds and a small waterfall, and with its sparse furnishing, the place has the feel of a treehouse. It also smells distinctly of dog – of which there are 10, rescued by Greenwald and his partner, David Miranda, whom Greenwald calls the “dog whisperer” for his Cesar Millan-like command over the pack. The dogs, which occupy every imaginable space there is, provide an ever-present backdrop to the couple’s domesticity, following Greenwald and Miranda from room to room and, from time to time, breaking into exultant barks for no real reason (other than maybe just the fact that they live in paradise).
Contrary to his confrontational persona, Greenwald is actually quite sweet in person, apologizing for his car, a somewhat beat-up, doggy-smelling, red Kia with tennis clothes tossed in the back, and a Pink CD case on the dashboard that Greenwald, 46, is quick to explain belongs to Miranda, who is 28. “I still listen to all the stuff I liked in high school – Elton John, Queen,” he says, shrugging, and then immediately wonders if it’s weird that “music just never spoke to me all that much.”
Politics, on the other hand, had a powerful hold on him from an early age. Originally from Queens, his family settled in South Florida, in the bland, cookie-cutter enclave of Lauderdale Lakes, then inhabited largely by ethnic, working-class families and wealthier Jewish retirees. The oldest of two, Greenwald was raised in a small house on the low-rent side of town, where his mother, “a typically 1960s-1970s housewife who married young and never went to college,” as he says, ended up supporting her sons by working as a cashier at McDonald’s, among other jobs.
Greenwald’s childhood role model was his paternal grandfather, Louis “L.L.” Greenwald, a local city councilman, and “sort of this standard 1930s Jewish socialist type,” who crusaded on behalf of the poor against the voracious “condo bosses” who controlled the city. In high school, Greenwald ran a quixotic campaign for a city-council seat, which he lost, but not before scoring a “moral victory” by simply challenging his entrenched opponents. “The most important thing my grandfather taught me was that the most noble way to use your skills, intellect and energy is to defend the marginalized against those with the greatest power – and that the resulting animosity from those in power is a badge of honor.”
This was useful advice for a gay teen growing up in the early 1980s, during the advent of AIDS, when “being gay was thought of, genuinely, as a disease, and so you just felt this condemnation and alienation and denunciation.”
Of course, all gay teens deal with their sexuality in different ways. “One is to internalize the judgment and say, ‘Oh, my God, I’m this horrible, sick, defective person’ – which is why a lot of gay teens commit suicide,” says Greenwald. Another, he says, is to escape the judgment entirely by creating an alternate world – “which is where a lot of gay creativity comes from because this world doesn’t want you.” Greenwald chose a third path. “I decided to wage war against this system and institutional authority that had tried to reject and condemn me,” he says. “It was like, ‘Go fuck yourselves. Instead of having you judge me, I’m going to judge you, because I don’t accept the fact that you’re even in a position to cast judgments upon me.'”
This began a lifelong struggle against authoritative structures, beginning with his teachers, with whom he engaged in epic battles over “unjust rules,” as Greenwald puts it. “Glenn was this supersmart, extremely obnoxious, eccentric kid, and depending on your sense of humor, you either loved him or hated him,” recalls his friend Norman Fleisher. “He was probably the smartest kid in the school, but it’s kind of a miracle that he graduated.”
Greenwald’s contrarian nature made him a star on the debate team, where he ran circles around his opponents and became a state champion. He enrolled at George Washington University in 1985, and spent so much time debating that it took him five years to graduate. After achieving a near-perfect score on his LSATs, he enrolled at the NYU School of Law, where, as a budding gay activist, he decided to “test the authenticity” of NYU’s liberal reputation by leading what became a successful campaign to ban Colorado firms from recruiting on campus after the state’s voters passed an amendment to overturn existing anti-discrimination laws.
After graduation, he accepted a job in the litigation department of Wachtell, Lipton, Rosen & Katz, called “America’s most grueling law firm,” which represented blue-chip clients like Bank of America, JPMorgan and AT&T. In his first year, Greenwald made over $200,000 – more money than he’d ever seen in his life. But he found the world of corporate law “dull and soul-draining,” he says. “I could not thrive or even function in a controlling institution like that. There’s a huge dichotomy between people who grow up with alienation, which, for me, was invaluable, and people who grow up so completely privileged that it breeds this complacency and lack of desire to question or challenge or do anything significant. Those are the types of people who become partners at the corporate law firms.”
In early 1996, the 28-year-old Greenwald, deciding he’d rather subvert the powerful than defend their interests in court, left Wachtell Lipton and opened his own practice. Consistently underestimated by big firms, he reached successful outcomes in case after case – often after deluging the opposition with motions and hundreds of pages of depositions – and insisted that his small staff wear suits, even while sitting around the office, to impose a sort of corporate discipline on a practice focused primarily on constitutional law and civil-liberties cases. He spent five years defending the First Amendment rights of neo-Nazis. It was one of Greenwald’s prouder accomplishments as an attorney. “To me, it’s a heroic attribute to be so committed to a principle that you apply it not when it’s easy,” he says, “not when it supports your position, not when it protects people you like, but when it defends and protects people that you hate.”
But law, even in its purest, most civil-liberties-oriented variety, was an ultimately frustrating endeavor, full of “unjust rules” and even fewer judicious outcomes. More interesting, particularly after 9/11, were the egalitarian conversations that were occurring online. Greenwald discovered this world in the mid-1990s when, bored at work, he’d begun cruising the CompuServe message boards, including Town Hall, a conservative forum created by the Heritage Foundation and the National Review. Instantly seduced by the chance to debate pro-lifers and other social conservatives, Greenwald soon began spending hours in heated arguments with disembodied strangers. He even, to his surprise, became friends with one or two. The Internet, he realized, was perhaps the only place where rules simply didn’t apply. “I believe in the clash of ideas,” he says, “and mine were being meaningfully challenged.”
These free-form debates were occurring in the virtual world at precisely the same time they were disappearing from the general discourse, submerged, as Greenwald says, in the wave of “nationalism and jingoism” that followed 9/11. Greenwald first began to realize how much things had changed in the political culture after the arrest of Al Qaeda “dirty bomber” José Padilla. “The idea that an American citizen could be arrested on U.S. soil, and then imprisoned for years, not charged, and delayed access to a lawyer, that always seemed like one line that couldn’t be crossed,” Greenwald says. “It was more than the fact that it was being done – it was the fact that nobody was questioning it. That was a ‘What the fuck is going on in the United States?’ moment for me.”
In the winter of 2005, Greenwald, seeking to transition away from practicing law, went to Brazil. On his second day of what was a planned seven-week vacation in Rio, he met Miranda, a handsome 19-year-old Brazilian who was playing beach volleyball not far from Greenwald’s towel. The two have been inseparable ever since. “When you come to Rio as a gay man, the last thing you’re looking for is a monogamous relationship,” Greenwald says. “But, you know, you can’t control love.”
Within a year, Greenwald had decided to relocate to Brazil, where, unable to practice law, he tried his hand at political blogging. Greenwald’s first week as a blogger, in October 2005, coincided with the indictment of Scooter Libby in the Valerie Plame leak case. Greenwald wrote a long post meticulously deconstructing the conservative argument against Libby’s indictment from a legal standpoint, which The New Republic linked to, driving thousands of readers to his site, Unclaimed Territory. Greenwald soon turned his attention to the explosive revelation that the NSA was spying on Americans under a secret, “warrantless wiretapping” program authorized by the Bush administration.
The program was exposed in a December 16th, 2005, article in The New York Times written by investigative reporters James Risen and Eric Lichtblau. But the Times, under pressure from the Bush administration and from Bush himself, had sat on the piece for more than a year. The paper finally published the story 13 months after reporting it, and a year after Bush was re-elected. “It was as disgraceful as anything the Times has ever done in terms of betraying what they’re supposed to be as a journalistic institution,” Greenwald says. “After that, I decided that I needed to sort out what was actually true, and what wasn’t.”
Another person who was bothered by the Times‘ treatment of the warrantless-wiretapping story – and a number of others based on classified leaks – was Edward Snowden, a patriotic young man who dreamed of a life in foreign espionage. “Those people should be shot in the balls,” Snowden, then a 25-year-old computer technician, posted to an online forum in 2009, criticizing both the anonymous sources who leaked and the publications that printed the information. “They’re reporting classified shit,” he said. “You don’t put that shit in the newspaper. . . . That shit is classified for a reason.”
Snowden grew up in the shadow of the biggest intelligence-gathering organization in the world – the National Security Agency – in the Anne Arundel County community of Crofton, Maryland. A solidly middle-class, planned community of 27,000 that Money has ranked as one of the “100 Best Places to Live,” Crofton, like the towns around it, fed the workforce of the defense and intelligence contractors in the area. The NSA, which employs tens of thousands of people in the public and private sectors, was just 15 miles away, at Fort Meade, whose high school boasts a “homeland-security program” to funnel kids into the industry.
Virtually everyone worked for the government or in “computer technology,” recalls Joshua Stewart, 30, who moved to Crofton in 1999. “You never really knew exactly what many adults did for money,” he says. There were houses with special secure phone lines – “bat phones,” as Stewart, now a reporter at the Orange County Register, called them. Some even had their own Sensitive Compartmented Information Facilities in their homes.
The son of civil servants – his father, Lon, served in the Coast Guard, and his mother, Wendy, is a clerk in the U.S. District Court in Baltimore – Snowden was a skinny, quiet boy who appears not to have made much of a mark on his former classmates or teachers. The Internet, he would later tell Greenwald, was his universe. He posted regularly at Ars Technica, the technology news and culture site, where, under the username TheTrueHOOHA, he chatted about video games and queried the more experienced geeks for help improving his computer skills. “I really want to know ‘how’ a real web server works,” he posted, at 18. He also pondered some of the philosophical underpinnings of life. “Freedom isn’t a word that can be (pardon) freely defined,” he wrote. “The saying goes, ‘Live free or die,’ I believe. That seems to intimate a conditional dependence on freedom as a requirement for happiness.”
Though brilliant by every account, Snowden had been an indifferent student who’d dropped out of high school in the 10th grade. After that, he drifted in and out of community college, but never earned a formal degree. In his late teens, he spent his days surfing the Internet, practicing kung fu and playing Tekken, while casting around trying to figure out what to do. “I’ve always dreamed of being able to ‘make it’ in Japan,” he said in one 2002 chat. “There have also been a couple studies that show out of qualified applicants, blondes are hired more often. . . . I’d love a cushy .gov job over there.”
But the path to success seemed unclear. At 20, as he wrote in one post, he was “without a degree or a clearance” in an area dominated by the NSA and its private offshoots. “Read that as ‘unemployed.'”
Like Bradley Manning, whose case he would later study, Snowden had an idealized view of the United States and its role in the world. He also had a gamer’s sense of his own ability to beat the odds – he’d later tell Greenwald that his moral outlook had been shaped by the video games he played as a kid, in which an everyman-type battles tremendous and seemingly invulnerable forces of injustice, and prevails. Following that ethos, and deeply affected by 9/11, Snowden enlisted in the Army in 2004, hoping to join the Special Forces and fight in Iraq. “I believed in the goodness of what we were doing,” he said. “I believed in the nobility of our intentions to free oppressed people overseas.” But he was quickly disabused of this idea – “Most of the people training us seemed pumped up about killing Arabs, not helping anyone,” he said – and months into his Special Forces training course at Fort Benning, Snowden later said, he broke both his legs and was discharged.
Back in Maryland, Snowden got a job as a security guard at the University of Maryland’s Center for Advanced Study of Language, a Defense Department-funded facility he would later describe as “covert,” though as The Washington Post pointed out, “its website includes driving directions.” He also re-enrolled at Anne Arundel Community College and burnished his computer skills. Then, in 2006, he landed a job as a computer technician with the CIA.
The CIA, with its air of entitlement and mystery, is the most elitist of U.S. government agencies. But the beauty of the IT sector, no matter where you were, as Snowden said, was its egalitarianism. “Nobody gives a shit what school you go to . . . I don’t even have a high school diploma,” he wrote in 2006. “That said, I have $0 in debt from student loans, I make $70k, I just had to turn down offers for $83k and $180k. . . . Employers fight over me. And I’m 22.”
In 2007, he was posted to the CIA station in Geneva. Mavanee Anderson, a young legal intern also stationed in Geneva, befriended Snowden and recalled him as thoughtful but insecure. “He talked a great deal about the fact that he didn’t complete high school,” Anderson later wrote in an op-ed for the Chattanooga Times Free Press. “But he is an IT whiz – I’ve always taken it for granted that he’s an IT genius, actually.”
Snowden came to be bothered by much of what he saw in the CIA. He would later cite an operation to recruit a Swiss banker as an asset that involved getting the man arrested on drunk-driving charges. He also recalled, in an interview with The New York Times‘ Risen, the retaliation from a senior manager whose authority he’d once questioned. The incident arose over a flaw Snowden found in some CIA software, which he pointed out to his superiors. Rather than praising his initiative, however, one manager, who didn’t appreciate such enterprising behavior, placed a critical note in his personnel file, effectively killing Snowden’s chance for promotion. He eventually left the agency, “experiencing a crisis of conscience of sorts,” as Anderson remembered. But Snowden also learned a valuable lesson: “Trying to work through the system,” he told Risen, would “only lead to punishment.”
As Snowden was navigating the intricacies of the U.S.-intelligence world, Greenwald continued to rail against the Bush administration and its policies, while also taking aim at the Democratic Congress for refusing to end the war in Iraq. In speaking engagements, and increasingly on television, he prosecuted his strategy to subvert the status quo by donning a suit and, in perfect and impossible-to-argue-against rhetoric, spouted the sort of radical ideology – pointing out the causal chain between U.S. foreign policy and terrorism – that would have landed anyone else in talk-show purgatory. Greenwald, though, became a regular guest on MSNBC.
“You have to learn the game,” he says. “I put on a suit. I speak in sound bites. I know what I’m talking about – and I don’t drone on and on. One of the main criticisms I have of Noam Chomsky is that he allowed himself to get marginalized by not ever strategizing how to prevent it. If you’re an advocate and believe in political values, your obligation is to figure out how to maximize your impact. Basically, my strategy has been, ‘I’m going to barge into every fucking place I can get and make my own access.'”
After Obama was elected, Greenwald alienated many of his former liberal allies by vowing to be as hard on the new president as he’d been on his predecessor. He was particularly critical of Obama’s “Look forward, not backward” mandate, which effectively immunized officials who’d committed felonies during the Bush years, even as the Justice Department began to zealously prosecute its own “war” on national-security whistle-blowers.
This “two-tiered justice system,” as Greenwald put it, was striking in the case of a former NSA official named Thomas Drake, whom Greenwald wrote about in 2010. Drake is famous in whistle-blowing circles for providing information to Congress about post-9/11 surveillance programs and disclosing information about mismanagement within the NSA including a costly, and failed, project, known as Trailblazer, to The Baltimore Sun. In 2010, he was indicted under the 1917 Espionage Act for mishandling classified material, though the government’s case against him ultimately fell apart. Nonetheless, the investigation cost him his job, drained his savings and ruined his reputation. Today he works at the Apple Store in Bethesda, Maryland. To Greenwald, and to Snowden, Drake would be a cautionary tale of what happens to dissenters who try to work within the system.
Drake, whom I meet in his lawyer’s office in Washington, is a tall, intense man with the earnest-yet-cynical bearing of a disillusioned Boy Scout. A former Navy intelligence officer, Drake spent 12 years in the private sector as a contractor, working as a systems software test engineer, among other positions. In 2001, he was hired by the NSA and assigned to its Signals Intelligence Directorate as part of an effort initiated by new NSA director Gen. Michael Hayden, to “stir up the gene pool,” as Drake puts it, and overhaul the agency, a Cold War institution, for the 21st century.
Though the NSA had once led the world in areas like cryptology and electronic eavesdropping, after the fall of the Soviet Union it was underfunded and without a clear mission. Its calcified management failed to anticipate the advances in fiber optics and cellular technology that would revolutionize the rest of the world, leaving the agency “on the verge of going deaf, dumb and blind,” according to NSA historian Matthew Aid. And it thoroughly failed to understand the importance of the Internet, says Drake. “The attitude was, nothing worth knowing is on the Internet, because it was open, right? They only wanted to know things that were closed.”
September 11th, which also happened to be Drake’s first day at Fort Meade, changed the equation. Drake explains the shift in two ways: The first was a massive expansion of U.S. spying capabilities as the agency “unchained itself from the Constitution,” and began to spy on Americans and foreign citizens, at home and abroad. The other change, felt across the entire intelligence community, was a rapid expansion of the NSA itself.
“Massive amounts of money were pumped into the NSA after 9/11, and Congress was saying, ‘How big do you want the check?'” says Drake. With virtually every agency involved in tracking terrorists clamoring for its SIGINT, or signals intelligence, the NSA expanded its outposts in Texas, Georgia, Hawaii, Colorado and Utah, as well as listening posts abroad, and also went on a building spree at Fort Meade, where the NSA’s sprawling 5,000-acre campus is now almost 10 times the size of the Pentagon. By 2013, according to The Washington Post, the NSA had expanded its workforce by one-third, to about 33,000. The number of private companies it depended upon more than tripled during that time.
Soon, thanks to this influx of money and the increasing reliance on the private sector to handle even sensitive jobs, the very heart of America’s intelligence infrastructure was being outsourced to contractors. “Essentially, 9/11 was a massive jobs program, in which the ticket you needed for the party was your clearance,” says Drake. “And tons of people were getting those clearances. So you had this huge apparatus being built, and the government was just managing it. And in some cases, they weren’t even doing that.”
Snowden, who left the CIA in 2009, was a natural fit for the NSA, which embraced the kind of problem-solving initiative his CIA bosses seemed to resent. “The NSA was very blue-collar, much more utilitarian than the CIA,” says Drake. “If you could prove your chops with computers, it didn’t matter what your background was, or what your grades were. We had a lot of people like Snowden at the NSA, who I hired. And there was no limit on the contracting side.”
Snowden was initially hired as a contractor for Dell, which had large contracts to maintain the NSA’s internal IT networks. He would also work for the megacontractor Booz Allen Hamilton, who last year earned $5.76 billion almost solely from government contracts, and is considered to be involved in virtually every aspect of intelligence and surveillance.
Within the world of the NSA, there is little difference between those employed by the agency and the private sector. Where there was a clear difference, was between the conventional management types and the scruffy hackers and IT geniuses who now filled the rank and file. “It was a weird world – there were these kids walking down the halls, and I never knew what color their hair would be when I’d see them,” says Richard “Dickie” George, a 40-year veteran of the NSA who, before retiring in 2011, oversaw the agency’s Information Assurance Directorate in the 2000s, hiring scores of young hackers. “They had ideas us older folk didn’t have, and we counted on that.”
To some intelligence insiders, it also made them a risk. “There was some discussions in the beginning of ‘We’re going after hackers, so how do we know that they’ll be good guys?'” says James Lewis, director of the Technology and Public Policy Program at the Center for Strategic and International Studies. “The real problem is that there’s a generational difference. You have an entrenched culture at the NSA, and suddenly you bring these kids in from outside, and they have very different attitudes toward information.”
By the time Snowden joined the agency’s workforce, the surveillance he would later expose was becoming not just institutionalized but very big business. “It was around 2009, 2010 that you saw the full flower of that massive, massive bubble of money,” says Drake. “And people were taking it for a ride as far as it could go.”
This system, however, was not without its internal problems. “When you hire all these contractors to do what were inherently government functions, you need the documents that authorize these kinds of access and operations,” Drake says. Paperwork was generated at record speed. Once-secret documents like FISA orders, which used to be stowed in special safes that only a few would be able to access, were now digitized and collected into a vast trove of electronic records that held the entire architecture of the national-security state.
Snowden began his NSA career in Japan, where he was given a fairly mundane job supervising upgrades to NSA computer systems. He̵