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.'"
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