Suddenly, I was aware of a tall and commanding figure sauntering, slowly, straight towards me. Carrying his large body with aplomb, he seemed in his element. Sabu. He grabbed my hand to shake it as we greeted. I was afraid my hand would shatter under the vise-like grip. I gathered my things and we went in line to order food. In the midst of our small talk Sabu paused, gave a nonchalant nod to the food prep worker (a tough looking Latina woman), and asked “What’s up?” She replied, “I have not seen you here in a while.” We moved to a table. The awkward and weird circumstances of our meeting were mitigated by the immediate ease of discussing a shared world of people and circumstances.

Seeing him in person, I confirmed, first hand, my suspicion that he would blow most hacker stereotypes to smithereens.

We all know the story of the lone wolf hacker who spends days and (more typically) nights coding software or rummaging uninvited through corporate servers in a dank basement lair. In most tellings he is a white, middle class, overweight male whose grease-stained shirt struggles to contain the abdomen protruding beneath but manages, thankfully, to catch the chip crumbs which tumble from his mouth between slurps of the largest Mountain Dew permitted by federal law. With a distinct nasal whine he autistically (and far too loudly) yells at any number of glowing screens arrayed around him like some kind of Star Trek battle station, excoriating some distant interlocutor — tearing them a new network interface and taking pleasure in the doing of it.

I had already begun to see that stereotype as bogus. Certainly it did not apply to those involved in what has, over the last five years, blossomed into Anonymous, the Internet’s first large scale counter-cultural insurgent protest movement. I ultimately met a handful of participants in person. Others were revealed for scrutiny upon arrest. Between these two mechanisms, I started to draw the basic outlines of an answer. As it turns out, there is no single kind. Their backgrounds and interests are disparate — except, perhaps, for a shared love of the geeky. Many of the hackers were also clearly willing to take on risk. Outside of these vague traits, the participants were a motley crew. Take for instance, the members of LulzSec, a breakaway group of hackers also involved in Anonymous. Besides Sabu—a Puerto Rican living in the towering public housing projects of New York who was also an occasional drug dealer and a foster father to his cousins—there were two Irish chemistry students, one whose radical political views were influenced by a father jailed for six years as a member of the Irish Republican Army; a Scotsman, who for much of his time in Anonymous lived on the remote Isle of Yell; and “Kayla”, a twenty-five-year-old man who had served time in Iraq as a soldier.

Something about the pseudoanonymity employed by Anonymous helped to engender this cosmopolitanism. Transparent networks are famously “homophilic”, to borrow a term used in sociology to describe a human inclination to associate with the like-minded. The conditions of pseudoanonymity seem to create a slight bias in favor of connections between dissimilar people.

Still, Sabu clearly stood in a class of his own. Following our first meeting, I could not help but think of Sabu as a savvier version of Oscar Wao, the titular character in Junot Diaz’s electrifying novel on the travails of being a corpulent, ostracized, “hardcore sci-fi and fantasy”-loving nerd of Dominican descent. Diaz describes Oscar bumbling through life between New Jersey and the Dominican Republic. Like that fictional character, Sabu is a consummate cultural boundary-crosser, flitting between vastly distinct cultural spheres. There are very few hackers from the hood. In fact, I only know of one other, John Threat, also from New York City. Threat holds the unique distinction of maintaining membership simultaneously in Brooklyn-based street gang called the Decepticons and an online hacker crew called Masters of Deception.

Was the opportunity for deceit diminished during face-to-face interactions? To a limited degree, yes. For instance, in the case of Sabu, he could not cloak his relationship to the neighborhood. He was a very well-known fixture in the East Village and many locals, whether in Tompkins Square Park, a restaurant, or simply along the street, greeted him with nods or handshakes. But away from keyboard (AFK) interaction does not eliminate guile entirely. Sabu was, after all, an FBI informant, a fact that I remained entirely unaware of— not for lack of suspicion. Sabu might have been my confidant, but he never won my trust. I was unsure then — and still am today — why he even reached out to me in the first place. We can never really access the inner thoughts of other humans; all we can do is attempt to gauge sincerity and authenticity. As Erving Goffman, a sociologists of micro-interactions, insists: such attempts are marred by difficulties.

“Behind many [social] masks and many characters, each performer tends to wear a single look, a naked unsocialized look, a look of concentration, a look of one who is privately engaged in a difficult, treacherous task.”

And yet, being uncertain and suspending mistrust are different things. Sitting with Sabu — seeing his face, hearing his voice, looking into his eyes and discussing a dizzying range of topics from family to gentrification, hacker culture and middle eastern politics, Occupy, his dog, the Anonymous haters and any other topic that his mind might alight upon in one of his long, weaving monologues — I found it easy to table my darkest suspicions. More than anything else, Sabu seemed to genuinely care about the opinions of others: not only about himself, but about the whole of Anonymous. His contempt for those critical of Anonymous — both journalists and random people on Twitter — was noticeable; he was always defiant. He jeered at those who he felt had not treated him, or Anonymous, with respect.

Now that time has passed and I know a lot more details about his role as an informant, some things have become more clear. But many still remain a mystery. Did he reach out to me of his own volition, or did the FBI ask him to meet with me? There are clues that point in both directions. For example, the following conversation, which happened the day after I first met him, seemed relatively mundane at the time:

Sabu: and ioerror is good people [ioerror = Tor developer Jacob Appelbaum]

Sabu: I’m trying to reach out to him

Sabu: I know hes been supportive of me in the last year

Sabu: I want to support him back

biella: yea he has

Sabu: during this time

biella: i know him well

Sabu: they’re trying to rail him

biella: for over 9 years now

Sabu: tell him I send my regards then

biella: i will for sure

Sabu: if theres anything we can do for him, to pass it through you

In the midst of this conversation I interpreted this as a reasonable gesture of solidarity. Appelbaum is a well known and respected hacker, artist, and journalist who has lived in Germany since May 2013 under self-imposed exile. After “four plus years of harassment,” and knowing his harassment would worsen after working with Glenn Greenwald and Laura Poitras on stories covering ubiquitous surveillance, “I decided it was not possible to work in the United States,” Appelbaum told me. So was this conversation a ploy by Sabu to ensare Appelbaum for his government handlers? The question hangs over me like a noose.

In a government memo calling for a lenient sentence, Hector Monsegur was deemed a model informant who helped nab a number of his close hacktivist associates: “Monsegur’s consistent and corroborated historical information, coupled with his substantial proactive cooperation and other evidence developed in the case, contributed directly to the identification, prosecution, and conviction of eight of his major co-conspirators, including Jeremy Hammond, who at the time of his arrest was the FBI’s number one cyber-criminal target in the world.”

With the benefit of hindsight, these chats — his motivations for reaching out to me in the first place — look all together different. The “we” he referred to was not Sabu and Anonymous. It was Sabu and the FBI. They were privileged with direct access to all his conversations, including the one above. It would not be the last time he tried “to reach out to” Appelbaum through me.

Following his exposure we had a few angry phone conversations. Faced with a barrage of defenses and qualifications, I barely ever got a word in edgewise. But I did manage to quiz Sabu on this very question: Had the FBI put him up to meeting me?

His voice became loud in dismissal. “Jesus Christ! You don’t need to ask permission to go to fucking Chipotle and get a burrito!”

Unsatisfied, I pushed the question — and referenced the catalyst for our meeting, a hacker I had encountered, with seeming casualness, at a security meet up. He began brushing this off, before suddenly stopping short. “I needed the truth out there one way or another,” he stated clearly. “The more time we spent, the more I felt I could confide in you. It is a shitty situation.”

Jeremy Hammond, FBI photo surveillance, Date: March 1, 2012

He let loose one final deluge of vitriol: “I expected the nerds to expose my family but not the media. For the media to post shit on my family!” Added an ambiguous tidbit: “There are many informants in Anonymous.” Then wrapped up our dialogue with some shout-outs, giving props to “Jeremy and Donncha,” two of the most technically savvy and hardworking hackers in Anonymous, who had themselves refused to offer anything to law enforcement, and whose capture had largely been the result of his actions. He parted with the following statement: “I still think the idea of Anonymous is beautiful. Decentralization is power.”

I can’t say whether or not Sabu believes — or ever believed — this statement. We do know that Sabu was uniquely charismatic, a skill he put to good use both towards and, ultimately, against the aims of Anonymous.

The respect and attention he demanded made him a valuable asset to Anonymous, and an equally valuable one to the FBI when they had him under his thumb. They did not have to train him nor prep him to do his work. He was simply “the influencer.”

As with much related to Anonymous, my reactions to Monsegur’s deceit exist in a Gordian knot of mixed feelings. These are sentiments I will probably never untangle to satisfaction. I could understand how Monsegur, facing over 100 years in jail, was backed into a corner. But just like Jeremy Hammond and many other Anonymous participants directly affected by Sabu’s actions, I felt betrayed. “Sabu avoided a prison sentence, but the consequences of his actions will haunt him for the rest of his life,” wrote Hammond, following a judge’s decision that the seven months Sabu had served for violating bail conditions were sufficient to stand for all of his charges. “Not even halfway through my time, I would still rather be where I’m at: while they can take away your freedom temporarily, your honor lasts forever.”

In the wake of it all, many questions remain. I often wonder why, after being correctly doxed previously, had Sabu remained in Anonymous? In mid-March 2011, a security group with a grudge against Anonymous, Backtrace Security, released a chart with the “identities” of seventy Anonymous participants and affiliates. Many of the names were either wrong or already public, except one. It was the one name that mattered the most at that moment: the notorious hacker Sabu.

Upon seeing his name, he could have wiped everything from his computer, gone dark, and returned decades later as a hacker hero. It is true that he could not have vanished right away. Doing so would have made “it obvious that he got doxed,” as Mustafa Al-Bassam, a fellow Anonymous hacker, reminded me. But why not slip away a month later, after accusations had died down and the question of the dox accuracy was forgotten? Instead, not only did he stay put, but he became even more public. Even more difficult to fathom was the stridently unapologetic stance he assumed when his role as snitch became public. Consistent with his character, he seemed genuinely angry that he was now treated as “a biohazard,” as he put to me on the phone — unable, or unwilling, to consider the many good reasons why his colleagues might suddenly desire to avoid him. Whatever the cause, whoever the benefactors, Sabu demanded things be seen through his logic.

Of all the uncertainties and questions that swirl around Anonymous, of all the misinformation, secrets and feints, there is one thing that became clearly resolved by Sabu becoming an informant. Sabu was defiant until it mattered, and now walks free, while Hammond, who was defiant even when it mattered, is now in federal prison for ten years. It was this defiant character that made Sabu so invaluable to Anonymous, but it was the weakness of this defiance that in the end made him invaluable to the Feds. It was his defiance, when put to the test, that turned out to be bluster and posturing and not the same kind of genuine principled defiance that Jeremy Hammond still holds. Meanwhile, those deceived by Sabu must replay their interactions over and over again, wondering what they could have seen, what they should have seen. I know I do.

Some of the material here is adapted, with permission, from Hacker, Hoaxer, Whistleblower, Spy: The Story of Anonymous, by Gabriella Coleman.

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