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.