Enemy of the State

How Glenn Greenwald is taking on the world, and why he'll never stop.



Grappling with the powerful head-on was more attractive to Greenwald than actual politicking or policymaking, so he went off to law school at NYU, graduated top of his class, and went to work for one of the most slickly prestigious law firms in New York: Wachtell, Lipton, Rosen & Katz. As a junior associate, Greenwald had a dazzling number of zeroes on his paychecks, suspenders on his shoulders, and wildly expensive shoes on his feet. He got access to the gilt-edged world of corporate law. But he only lasted 18 months. “I just wanted to know I could enter this world of power,” he says. “It was riveting and exotic. But I wanted to prove that I could conquer it and that there was not a part of that world that wasn’t accessible to me.”

Part of Greenwald’s decision to leave his firm was over a pair of Rollerblades. His then-long-term boyfriend bought a pair, strapped them on, fell, and broke both his wrists. Greenwald sued Rollerblade on his boyfriend’s behalf, but his firm protested: They hadn’t given him permission, and what if Rollerblade had been a potential client? “I can’t deal with constraints like that,” Greenwald says with a tinge of self-effacement. “I chafe at any restraints on what I can do or say.”

He used his year-one bonus to start his own law firm with a small, scrappy, staff that specialized in constitutional law and civil rights. There was a strict dress code: Everyone had to be in suits all the time. To this day, Greenwald wears sober suits whenever he makes any public appearance — no open-shirted radical with a shaggy haircut here. He did five years of pro bono work defending neo-Nazis, among other unpopular clients, over First Amendment issues. Eternally restless, Greenwald predictably found too many constraints in the practice of law as well. “I was pouring my energy into these
institutions that were created to yield these unjust outcomes,” he says. “So it just felt like hitting your head into a brick wall.”

Greenwald’s focus drifted away from the courts, and by mid-decade he was spending more and more time online, stirred by the fuck-all attitude of insurgent political bloggers who were trying to break the stranglehold that stodgy mainstream institutions like the Washington Post and CNN held over political discourse. “This was a time when Ezra Klein, who is now, like, the mayor of Washington hack media, used to write things like ‘Fuck Tim Russert with a spiky acid-tipped dick!’” Greenwald cackles gleefully. Klein has since apologized for his thorny phallus comment, saying “it haunts [him] to this day.” In 2005, Greenwald started his own blog, where, as he puts it, “I could say whatever the fuck I wanted, however I wanted,” and has since apologized for absolutely nothing.

Back before the words Google and Zuckerberg were branded on our psyches, Greenwald was seduced by the strange and unruly promise of Web 1.0. He would argue for hours with strangers on right-wing message boards and experiment with different identities, sexual and otherwise, in chat rooms and over instant messaging, all in service of what he describes as a fundamental part of his self-exploration. It’s only inside a private, anonymous space, away from judgmental eyes, that people can violate orthodoxy and explore new boundaries, Greenwald argues. “The private realm is where creativity, dissent, and innovation exclusively reside,” he says. Even the most radical exhibitionist has parts of their life that they want kept hidden, he reasons. “If you eliminate that private realm, you breed conformity. When all your behavior is public, then you’re going to do the things that the society insists you do and nothing else,” Greenwald says, “and you lose so much of who you are as a human being.”

At left: Edward Snowden

 “When I was talking to strangers over the Internet in the 1990s, there would be a much more intense connection because they’re disembodied, so it’s just your brain and your soul interacting with this other person and it just frees you up in this incredibly empowering way,” he says over fries at an outdoor café in Leblon, the Beverly Hills of Rio. Over our heads looms a huge poster of an illustrated magazine cover that depicts a bespectacled Snowden gently kissing Vladimir Putin while he surreptitiously places a “Free Pussy Riot” sticker on the Russian prime minister’s back. Greenwald sneers, “I hate that cover. It’s so stupid.”

Greenwald concedes he gets “a little mean” when asked about his or Snowden’s feelings on Russia. “I’m well aware of the flaws in Russian society, just like I’m well aware of all the flaws in American society,” Greenwald says. “Thousands of people apply for and are given asylum in the U.S. every year, and nobody says, ‘Isn’t it so weird and ironic that people are applying for asylum in a country that has an ocean prison where people are put in cages without trial for 10 years, uses drones, or torture?’” he says, half annoyed. “The point of asylum is not to declare to the world what country you think is the pinnacle of civilization. The point of asylum is to find a country that’s both willing and able to protect you from political persecution.” Greenwald adds, “In no way is asylum an endorsement of a country’s politics, laws, or values. He didn’t choose to be there. He was trying to get transit to Latin America, and then the U.S. revoked his passport and threatened other countries out of offering Snowden safe passage.”

At the end of Greenwald’s trip to meet Snowden in Hong Kong, he was convinced that Snowden would be snatched up by the U.S. and held in custody without trial for years, much like whistleblower Chelsea Manning, whom Greenwald considers a hero. Manning’s three-year pre-trial incarceration and 35-year sentence proves, Greenwald says, that Snowden was right to find harbor anywhere he could. “The question shouldn’t be why is Snowden in Russia? The question should be why is America no longer safe for whistleblowers?”