Photo: Polaris

On the day that he joined forces with the hacker collective Anonymous, Hector Xavier Monsegur walked his two little girls half a dozen blocks to their elementary school. “My girls,” he called them, although they weren’t actually his children. Monsegur, then 27, had stepped in after their mother—his aunt—returned to prison for heroin dealing.

After he dropped off the girls, he walked to his apartment at 90 Avenue D, in the Jacob Riis projects, where he’d lived virtually his entire life. He passed through the dimly lit lobby, took the beat-up elevator to his floor, and went into apartment 6F. Monsegur’s prized possession was a computer, dilapidated but serviceable, its keyboard missing the shift, 7, and L keys. He sat down and went to work.

In the projects, Hector Monsegur was far from a tough guy. He was a bit of a nerd, in fact. But online he became an entirely different person—Sabu, he’d christened himself. “I’m a wild nigga,” he typed in a December 2010 chat. “Everyone knows me for my behavior … and I’m here like a pit bull wanting to own,” which is to take over other people’s computers and, sometimes, their entire identities.

The same month Monsegur typed those words, Anonymous, which had been up and running for a couple of years, was planning what hackers hoped would be its most dramatic attack yet, on PayPal and certain credit-card companies, in retaliation for their suspending services to WikiLeaks. Sabu, along with 4,500 other hackers and volunteers from around the world, activated a simple program that, when launched, would bombard PayPal’s site with requests—“packeting,” Sabu called it—overloading its servers.

The PayPal attack was not a rousing success—the site slowed for a couple of hours on December 8, 2010, but Monsegur was inspired and pushed ahead with other attacks. Within six months, he became perhaps the most influential hacker in the world, leading hacker actions against multinational companies and governments, helping turn Anonymous into a cross between an outlaw gang and a worldwide protest movement. And then, after he was arrested, he became an FBI informant—and he was gifted at that, too.

That one of the world’s most influential hackers was the denizen of a New York City housing project struck many as cognitively dissonant. It shouldn’t have. In many ways, he’s a product of the culture of poverty he was brought up in. It’s a culture that produces outlaws of many different stripes. Monsegur was born in 1983, when his ­father was 16. His mother deserted the family, and his father entrusted his son to Monsegur’s grandmother Irma, 40 at the time. Irma, born in Puerto Rico, never mastered English, but she was devoted to her grandson, a quiet, well-behaved child whom ­everyone called Bubi. But child care was not his grandmother’s only vocation. She was “a player,” as a family lawyer said, and her apartment was a stash house for the family’s heroin business. Sabu’s father was a lead distributor, as was his aunt, a long-haired beauty; Monsegur was described as a delivery boy. Heroin was good business, and for a time, “the family was really powerful in the hood,” said a neighbor. ­Sabu’s father led the life of a successful entrepreneur, seeming to change cars and women monthly. He liked to peel bills from a wad of cash and treat all the neighborhood kids to ice cream.

In 1997, the high life abruptly ended when the family was busted. Monsegur’s grandmother escaped with probation. But his father, then 30, was sentenced to at least seven years in state prison, as was his aunt, 27. Monsegur was 13 years old. He was a big kid—as an adult, he’d be six feet tall and heavy, pushing 250 pounds. He could hold his own in the projects, but he didn’t quite fit in. “He didn’t play sports with the rest of us,” said a neighbor who grew up with him. “He wasn’t a hood kid. He was a brain. If you talk to him, he don’t talk like us. He talk educated.”

For Monsegur, the computer was his refuge. “When he closed his eyes, he could see Sweden and Tunisia,” said Stanley ­Cohen, a lawyer who’s known him for years. Even as a teenager, Monsegur had awesome computer skills—at 14, he taught himself to program in Linux, the open-source operating system, and hacked his way to a free Internet connection. His hacking life began in earnest the next year, 1999, after a Puerto Rican was accidentally killed during a botched bombing run by a Marine Corps plane near a test range on the island of Vieques. The incident spurred protests in Vieques as well as in some Puerto Rican neighborhoods, and Monsegur joined in online. It was, he later wrote, his political awakening. He went on a defacing spree, substituting his own homepage for those of random sites—he became a kind of online graffiti artist. On one defaced site, he announced, “I’ll be your Puerto Rican defacer.” He continued tentatively. “Hello, I am ‘Sabu,’ no one special for now,” he wrote on one site. But then he shifted into another gear. “The U.S.A. has treated Puerto Rico and it’s citicenz like shit.” The message concluded with a plea: “all I want is the respect that I deserve,” he wrote, then threatened: “Or should I take it by force?”

Photo: Robert Stolarik/New York Times/Redux

The Jacob Riis projects offered stunning views of the East River, but from inside the scenery looked different. Shit occasionally festered in the halls. Residents tended to be suspicious of the world outside it. “People think we in the projects are grimy,” one of his neighbors told me. And Monsegur, no matter his online prowess, had shared that sense of feeling small in the world’s eyes. “He thought others were constantly judging him,” said Michel Blomgren, a Swedish friend with whom he chatted online for hours. “To him, they were making assumptions based on how he looked and where he lived.”

Monsegur attended Washington Irving High School near East 16th Street, a school where, in his era, only 55 percent graduated with their class. Monsegur was one of the bright kids, with seemingly few limits on his future. Then one day he walked through the school’s metal detector and was stopped by the chief of security, who found Monsegur’s screwdriver, according to an essay he posted online.

“Why are you carrying a screwdriver with you?” the security guard demanded.

“I am the geek that fixes your [computer] system,” Monsegur replied with apparent irritation.

“Hey, don’t give me attitude, boy,” he said.

“I am not giving you an attitude, I am telling you that … I am a student and I work on the school’s nonfunctioning computers.”

The guard stared him down.

“Fellow students watched the incident and witnessed this man … treat me like I was inferior, [and] totally disrespect me as well,” he wrote.

Monsegur, according to his own account, complained in a letter to school administrators—which didn’t work out as desired. They found the letter “threatfull,” as Monsegur put it, and a teacher phoned to tell him he was “temporarily expelled.”

Monsegur responded that “it is such a shame that one … such as myself would have to be deprived of my education because of my writing.” He called the security guards “abnormal subhuman arrogant dropped-at-birth gene defective infidels.”

Meanwhile, on the Internet, Monsegur was racking up successes. He had a gift for organization, and in May 2002, when he was 18, he announced with “ecstasy”—and, he suggested, on ecstasy—that he’d launched a club for programmers. “I am calling out to all the New York City Python hackers out there to come, integrate their knowledge into one big mass of hairy information.” The programmers’ club was added to another project, this one closer to his heart: pure-elite.org, which he referred to as “My child; My birth; My manifestation.” It was essentially a clubhouse for teenage rebels to chill, play online games, and, in a similar spirit of adventure, penetrate powerful computers. He was soon working on “a full-fledge IDS [intrusion-detection system],” wrote Monsegur. Pure-elite even helped Monsegur meet a girl—from Oklahoma. “I love you because you are awesome,” he wrote on her MySpace page. She responded: “my relationship fucking rocks.” The two probably never met in person.

For Monsegur, the Internet was a place where he could aspire. To his friend Blomgren, he wrote about his determination to escape the “ghetto mentality with everyone talking shit and angry at society.” And he took steps in the real world to make it happen, landing a spot at NPower NY’s Technology Service Corps, which prepares disadvantaged young adults to become IT professionals; then in 2002 he worked as a technology intern at iMentor, which “improve[s] the lives of high-school students from underserved communities.”

In 2004, from Sweden, Blomgren launched an Internet-security firm called Tiger Team and recruited his clever young friend, but Tiger Team never took off. After­ward, Monsegur worked sporadically. He landed a job at Openplans.org, a nonprofit trying to improve transportation systems, but was reportedly fired after a few months. He’d earned as much as $6,000 a month at one point, but the jobs never quite added up to a career, and after April 2010, he was unemployed.

Monsegur still lived with his grandmother in her two-bedroom apartment, which soon received two more residents. In 2009, his aunt was arrested again for heroin dealing, and her two little girls were passed to Grandma Irma. (Monsegur’s father, released from prison, had been banned from even visiting Jacob Riis because of his conviction.) Then, on June 7, 2010, his grandmother, who had long suffered from diabetes, died at age 66 at Beth Israel Medical Center. Monsegur’s father didn’t show up at the hospital; his aunt was escorted under guard and permitted to stay for an hour, before she was returned to Rikers Island. Monsegur, alone with his grief, was inconsolable. His grandmother had been the most dependably loving figure in his life. “She’d raised him since he was a baby,” said his mother’s sister, who lives in Brooklyn. “He was a grandma’s boy.” She remembered that he cried and cried.

Photo: From left: AFP/Getty Images; Rex Features via AP Images; Peter MacDiarmid/Getty Images

With her death, Monsegur’s life tilted on its axis. At 26, he became head of a household, taking over as parent to his aunt’s two children, both under 7 at the time. It wasn’t a job he wanted. “I took up the responsibility out of consequence,” he wrote in one chat log. “My family is small. I did not want the girls to go through the system.” If he didn’t take them, the city might. One neighbor told me, “He sacrificed his life for those girls.”

Still, Monsegur was a proud parent, even if the job overwhelmed him. “Being a parent ain’t easy,” he wrote to an online friend. “… So much shit going on at the same fucking time.”

And with the two girls to support, Monsegur’s tenuous financial condition became a crisis. He’d been living on unemployment benefits of $400 a week. By December 2010, six months after his grandmother’s death, and the disappearance of her Social Security check, he was desperate. “He was angry and frustrated about losing his job,” said a person who talked to him at the time. “That’s what threw him into the hacker scene.” Monsegur began to lead a double life. In the physical world, he wanted to be a responsible parent, even if he dabbled in crime, trying to move a pound of marijuana in that period. But his online persona was increasingly out of control. He didn’t seem to recognize limits or laws. In December, 2010, Sabu went on a crime spree. “I only hack for profit now … gotta make that money,” he wrote to Kelly Hallissey, an ­online interlocutor, that month.

On December 6, he sent a message from his Facebook account: “Yo papi I just got a corporate account that has at least 400k in it,” then supplied apparent account information, presumably so the account could be looted. On December 13, he sent the same person the credit-card and Social Security numbers for a couple of dozen people. He claimed to have gotten some information by downloading PDFs of TurboTax returns via Google. He obtained stolen credit-card numbers. “I used these [cards] … to pay my own bills,” he later admitted. He got ahold of a former employer’s credit-card information, and hacked into an auto-parts company’s computer system and had four engines worth $3,450 shipped to him. Monsegur turned himself into a kind of comic-book supercriminal. “You clearly don’t know anything about me,” he wrote to a friend in late December 2010. “How about you ask who sabu is first before you talk shit before you get owned into next year.”

But crime-for-profit quickly became a sideline to Monsegur’s real business on the web, which was attacking powerful institutions. Monsegur later said that Anonymous was the movement he’d been waiting for all his life. “It lives, it thinks, it breathes,” he said. “We give police officers in the United States the power to shoot us and get away with it. Anonymous can now stand up to that threat.”

As a movement, Anonymous had its roots in the online adolescent playpen 4chan, and many hackers joined up for the “lulz,” which included goofy and inconsequential schoolboy pranks, like having pizzas sent to a target’s home. Some Anonymous hackers wanted to do little more than sow mayhem—to “fuck shit up,” as one explained. Or, to use a favorite word, perpetrate “motherfuckery.” Sabu distinguished himself by being deadly serious. His rhetoric, redolent of the most radical of sixties activists, thrilled and inspired his online comrades. “He played the principled warrior,” said Samantha Murphy, a journalist who followed the chat rooms. “He gave them a reason to be angry and made it into a real rebellion.” And he embraced his roots. Once he had hoped to trade a life in the projects for a career. Now he was “talking shit and angry at society,” like the people he’d grown up with. “My nigga” and “my brother,” he called fellow hackers, most of them young white kids. Anonymous was said to be leaderless, but strong personalities dominated, and Sabu’s was one. He issued commands: “Use your skills to disrupt the governments communications for the cause,” he tweeted. He scoped out targets, mentioning one law firm. “I see some potential openings … we could rape these niggers,” he wrote. He bullied people into line and at the suggestion of insubordination meted out discipline. “I’m about to start owning nigg3rs,” he wrote.

Sabu’s online fame grew along with Anonymous’s notoriety, and his anger helped shape Anonymous’s identity. He sympathized with the marginalized. And if the lulz were a driving force, Sabu helped make fighting oppression another. By January 2011, the Middle East was erupting—in part owing to WikiLeaks’ revelations. From his apartment in the projects, Sabu took control of a local Tunisian’s computer and, as he’d done after Vieques, defaced the website of Tunisia’s president—he posted an Anonymous logo. For Sabu, it was a peak experience. “You don’t know the feeling of using this guy’s Internet to hack the president’s website,” he later told Parmy Olson, author of the just-published We Are Anonymous, a remarkable inside account of the hacker movement. “It was fucking amazing.”

Meanwhile, Monsegur’s real-world life was coming apart. Monsegur was devoted to his girls and wanted to do well by them. But he seemed to have given up on maintaining any semblance of normal home life. His apartment became a kind of frat house where Monsegur, his relatives, and his friends partied into the night. One neighbor complained repeatedly—and ­others joined in—claiming that he and ­others were “pounding, rapping, and screaming to loud music,” sometimes until 4 a.m. When the neighbor knocked on his door, he told her, “Get the fuck out of here,” she said.

Then in January 2011, the NYC Housing Authority informed him that because his name wasn’t on his grandmother’s lease, he was subject to eviction. But Monsegur missed five consecutive appearances at landlord-tenant court just a few blocks away. Finally, an indulgent judge offered him a second chance. He could take over his grandmother’s lease, and her $517-a-month rent, if he paid the back rent owed—$5,146 as of February 2011. But Monsegur never came up with the money. “I don’t think he cared anymore,” said a Housing official who spoke to him.

Online, Sabu had joined a small, ultraskilled group of Anonymous hackers—its SEAL Team Six. He’d been involved in cyber attacks against government systems in Tunisia and Algeria, but this elite group’s hack of computer-security company HBGary Federal burnished the Anonymous brand—skilled, dangerous, vindictive, and capable of anything. “I’m the one that did the [HBGary Federal] op,” Sabu later bragged, though it wasn’t entirely true.

After HBGary Federal’s CEO, Aaron Barr, claimed he knew the real identities of certain Anonymous leaders, a boast to promote business, a hacker called Kayla helped break into the company’s computer system. And Sabu conned the company’s security systems administrator—“social engineering,” it’s called in the hacker world—e-mailing him from what appeared to be an HBGary account and getting him to give up an administrative password. They stole and posted roughly 50,000 of CEO Barr’s e-mails, which inadvertently revealed that the supposed good guys were proposing some shady business—like discrediting Salon’s Glenn Greenwald, a very vocal supporter of WikiLeaks. HBGary Federal suggested infiltrating groups and spread disinformation, tactics that disturbed some members of Congress enough to call for an investigation.

For Sabu, the stakes were rising quickly. The FBI had been trying to track him for months. And now, so were other hackers who viewed themselves as patriots. First, Hallissey revealed his real name. Then Jennifer Emick, a Michigan housewife, who had once been sympathetic to Anonymous, released a spreadsheet of roughly 70 supposed real names of Anons in March 2011, taking up where Barr had failed. Most were wrong, but she had Sabu right (though she misspelled his name). Sabu had slipped up, once posting the address of his private server, which led her to pictures of a favorite vintage car, which was traceable.

Sabu denied Hallissey’s and Emick’s claims—“It’s jeremy,” he wrote—but being named weighed on Sabu. And so did the prospect of getting caught. The past summer, the FBI arrested fourteen purported hackers across the country for allegedly attacking PayPal. By April, Sabu talked of quitting. But then hackers from the HBGary Federal team suggested getting the old crew back together—reuniting the band. Sabu had missed the camaraderie and the intensity of a daring mission. By May, the group had reassembled and launched an offshoot of Anonymous, LulzSec—which, over 50 days, conducted a reign of Internet terror like few before it. Sabu had once viewed himself as a principled warrior, but now he joined in wreaking havoc—indiscriminate havoc. Sabu and LulzSec hacked Fox.com, Sony Corps, the U.S. Senate, in some cases posting personal information and e-mails. They hacked PBS, where they posted a fabricated story claiming that Tupac Shakur was alive. Sabu found a weakness in the FBI-affiliated InfraGuard. On June 3, 2011, dubbed Fuck FBI Friday, they defaced InfraGard’s Atlanta website and released personal information. The Wall Street Journal published an article about LulzSec: Almost anyone is a target, it reported.

LulzSec was the new star of the hacker scene, and in chat rooms random hackers passed along computer vulnerabilities or even stolen information. Pointless ­internecine feuds escalated. Under the banner of LulzSec, one kid “packeted” ­cia.gov—“for the lulz,” tweeted LulzSec. Others packeted each other. LulzSec had become chaotic, and some core members soon wondered if it was worth continuing. Then Sabu disappeared for almost two days, which was a worrying occurrence.

After nine on the warm night of June 7, 2011, the anniversary of Monsegur’s grandmother’s death, tall, balding FBI special agent Christopher Tarbell and a second agent, wearing bulletproof vests, entered the gloomy lobby of 90 Avenue D, walked to the sixth floor, and knocked on Monsegur’s brown door, to which is affixed a torn bumper sticker with an American flag.

Monsegur answered. In photos, he sported two shiny earrings, short hair, and a well-tended goatee. That night, he wore jeans and a T-shirt. “I don’t have a computer,” he protested, though the cables were in plain view. The FBI had known Sabu’s true identity for weeks—Emick told me she’d been contacted by the FBI soon after she released details of his identity. On June 7, they subpoenaed Monsegur’s Facebook account and discovered the messages to “papi” that implicated him in aggravated identity theft, enough to move against him. If convicted, he faced a minimum of two years.

The agents reminded him of his two girls—who must have been asleep in the apartment at the time. “He was terrified for his kids,” said an attorney briefed on the arrest. The agents let him know that if he proved a productive informant, he might receive a lighter sentence—how light depended on his productivity. Sabu the revolutionary had often vowed to go down honorably. “I’m the martyr type I grew up in the streets. I’d rather go down for my own shit than take down my own niggas,” he boasted. But that was bluster. When an agent shouted that the deal was off, Sabu quickly agreed to cooperate.

The next day, June 8, Monsegur was secretly arraigned in a federal courtroom in lower Manhattan and released on his own signature. In a form filed with the court, Sabu stated that he had $100 in available funds at the time and owned nothing of value.

It was as an informant that Sabu signed into a LulzSec chat room on June 24 and learned that his comrades were dropping out of the movement. He needed them to commit crimes, so he could help the FBI bust them, but Sabu also seemed truly hurt. “You guys can go,” he wrote, resigned. “I’m fucked sooner or later, so I got no choice but to continue.” He told them he’d reached “the point of no return,” a phrase he’d often repeat.

Once he became an informant, the authorities finally accorded Monsegur the respect he felt he deserved, praising his work ethic and his savvy. And Sabu overachieved for the FBI, working diligently “since literally the day he was arrested,” an assistant U.S. Attorney said. He was “staying up sometimes all night … helping the government build cases” against friends who the US government later called his “co-conspirators.”

The FBI replaced his computer and installed key-logging software on a new one. They rigged his apartment with video-monitoring equipment. He sometimes worked out of FBI offices, but even when home, agents monitored every letter he typed and every move he made.

Sabu found that he enjoyed his new role, and the power that came with it. Once he identified with the marginalized; now he favored the special agents in coats and ties. “Informants want to be liked,” explained a former top prosecutor. “And they want to do something they feel is successful.” Indeed, Sabu assumed this new identity with a little too much ease. On February 3, 2012, an NYPD officer stopped Monsegur in his building in the projects. Monsegur was asked for his I.D. “Relax, I am a federal agent,” he said. After Milan Patel, an FBI special agent, refuted his story, Monsegur was charged for impersonating an officer.

He didn’t let the snub bother him. “Once he’d been caught, it was like he thought, Why not just enjoy it?” said Olson. Two weeks after his arrest, Sabu tweeted: “Operation Anti-Security—The biggest, unified operation among hackers in history. All factions welcome. We are one.” AntiSec was the movement that succeeded LulzSec, and it was Sabu’s baby as well as an FBI front. Sabu urged on hackers, inciting them to commit crimes, with the apparent approval of the FBI. (The FBI wouldn’t comment.) On January 30, 2012, under the watchful eye of federal agents, he tweeted: “Hackers around the world unite. Help your brothers and sisters. Use your skills to disrupt the governments communications for the cause.” On January 20, 2012, he tweeted: “We need to hit their pockets.” As a double agent, Sabu needed to stay in role, but there were times when he let his guard down, Sabu became friends with Kieshu Zykova, as she was known online—her real name is Bethany Woolridge. She was an Anonymous groupie. “I was obsessed with Sabu,” she told me. “I was overjoyed he was interested in me.” At first, Sabu dutifully worked her for information, but soon the talk turned intimate. Zykova talked of coming to New York to be with him. Sabu put her off. He knew what the future held. “Now that I look back … many times he tried to protect me and get me out of that scene.”

With others, though, Sabu was ruthless. Mike Nieves, a legendary hacker who online goes by the name Virus, believes that Monsegur targeted him, trying to maneuver him into doing something ­illegal. In person, Nieves, 22, is not much over five four, with a habit of looking away when speaking, as if checking for exits, but he’s a tough kid. He told me he’d dropped out of school in the ninth grade rather than get booted for fighting. “It was fun,” he said of his post-school days. “I hung out, got drunk, and hacked AOL.” When he was 17, he was arrested for that last bit of fun. Afterward, he occasionally checked into chat rooms, and on August 11, 2011, he chatted with Sabu, who, in an apparent diversionary tactic, accused him of snitching for the NYPD: “my nigga ­jesus. at least inform for the FBI or secret service not the NYPD LOL thats like lowest of the lowest form. ya smell me?” Sabu wrote without irony.

“you’re a faggot bro,” Virus responded. “don’t start accusing me of shit.” He pointed out that Sabu had offered him money for some stolen information. Nieves sensed something was wrong, and told Monsegur so—“you disappeared and came back offering to pay me for shit—that’s fed tactics.” Sabu retreated, assuring Virus that he loved him like a brother, but a cynical Virus couldn’t be had. “It’s the internet,” he wrote back to Sabu. “There’s no love on the internet.”

But that wasn’t always true—Sabu inspired loyalty. Even though Monsegur had retired (as part of his plea agreement) from active hacking, he continued to be a revered leader in the movement. “You just get me,” wrote one young hacker. When this hacker thought of quitting, Sabu talked him down, explaining, “You can’t quit an idea, my love.”

What many didn’t suspect was that at that moment, the unquittable idea was a federal investigation. Hackers passed Sabu computer vulnerabilities, as many as a couple of dozen a day, which he fed to the FBI, which hurriedly contacted the vulnerable companies. Sabu was finally the security expert he’d once hoped to be. By the Assistant U.S. Attorney’s account, he helped plug 150 holes in computer systems. Sabu also thwarted ops by force of personality—when hackers wanted to attack Wall Street at the time of the Occupy Wall Street movement, the FBI told him to shut it down and he did, according to Olson.

On March 6 of this year, Sabu’s run finally ended. Authorities in Europe insisted on rounding up suspects produced by their own investigations of Anonymous, so the U.S. Attorney’s office had no choice but to reveal Sabu’s role. As part of a coordinated worldwide sweep, Kayla and other alleged members of LulzSec who had been said to have collaborated closely with Sabu were among those charged.

In the space of a few weeks, Monsegur’s life changed completely. Sabu the revolutionary warrior disappeared from the Internet without a trace. And by then, Monsegur had also vanished from the projects. A month before his outing by the FBI, a city marshal had shown up at apartment 6F, a locksmith in tow. Monsegur was already gone. The marshal found nothing but a few boxes of children’s clothes and toys. Monsegur is said to be somewhere in the neighborhood, awaiting sentencing. His girls, for whom he’d become a snitch, are no longer his charges. Child Protective Services was said to have taken them to their mother, Sabu’s aunt, who’d been released from prison.

On the Internet, Monsegur was now a reviled figure. At Jacob Riis, it was a different story. Those who knew him growing up were shocked—he was always “respectful,” they said. But also, they were a little proud. In their eyes, he was a kid from the projects who’d achieved a certain success. He’d gotten out, finally. “The government wanted him. That’s how good he is. He’s like the greatest hacker in the world. To me, I look up to him,” said one of his boyhood friends.





This story appeared in the June, 11, 2012 issue of New York Magazine.