This is an interesting (but long) profile in the New York Times of a hacker, turned government informant/consultant, who managed to continue his criminal activities under their noses. I'll include the excerpts that scream sociopath (or autism, really):
“He could be very disarming, if you let your guard down. I was well aware that I was dealing with a master of social engineering and deception. But I never got the impression he was trying to deceive us.”
Gonzalez’s gift for deception, however, is precisely what made him one of the most valuable cybercrime informants the government has ever had. After his help enabled officials to indict more than a dozen members of Shadowcrew, Gonzalez’s minders at the Secret Service urged him to move back to his hometown, Miami, for his own safety. (It was not hard for Shadowcrew users to figure out that the one significant figure among their ranks who hadn’t been arrested was probably the unnamed informant in court documents.) After aiding another investigation, he became a paid informant in the Secret Service field office in Miami in early 2006. Agent Michael was transferred to Miami, and he worked with Gonzalez on a series of investigations on which Gonzalez did such a good job that the agency asked him to speak at seminars and conferences. “I shook the hand of the head of the Secret Service,” Gonzalez told me. “I gave a presentation to him.” As far as the agency knew, that’s all he was doing. “It seemed he was trying to do the right thing,” Agent Michael said.
At his sentencing hearing in March, where he received two concurrent 20-year terms, the longest sentence ever handed down to an American for computer crimes, the judge said, “What I found most devastating was the fact that you two-timed the government agency that you were cooperating with, and you were essentially like a double agent.”
Gonzalez’s closest friend, Stephen Watt, who is now serving a two-year prison sentence for coding a software program that helped Gonzalez steal card data, describes Gonzalez as having “a Sherlock Holmes quality to him that is bounded only by his formal education.” Like the other hackers who would go on to form the inner circle of Gonzalez’s criminal organization, Watt met Gonzalez when both were teenagers, on EFnet, an Internet relay chat network frequented by black hats. Watt and Gonzalez interacted strictly online for a year, though each lived in South Florida. Once they began spending time together, in Florida and New York, Watt, who is 27, noticed that Gonzalez’s talents as an online criminal carried over into his life away from the computer. “He could spot wedding rings at 50 yards. He could spot a Patek Philippe at 50 yards. He would have been a world-class interrogator. He was very good at figuring out when people were lying.”
Like many hackers, Gonzalez moved easily between the licit and illicit sides of computer security. Before his first arrest, in the A.T.M. lobby, Gonzalez made his way from Miami to the Northeast after he hacked into a New Jersey-based Internet company and then persuaded it to hire him to its security team. The transition from fraudster to informant was not too different.
“I did find the investigation exciting,” Gonzalez told me of turning against Shadowcrew. “The intellectual element. Unmasking them, figuring out their identities. Looking back, it was kind of easy, though. When someone trusts you, they let their guard down.”
Indeed, no one I spoke with compared him to a gangster or a mercenary — preferred honorifics among hackers — but several likened him to a brilliant executive. “In the U.S., we have two kinds of powerful, successful business leaders. We have people like Bill Gates and Steve Jobs, who are the most sophisticated of electronic technicians and programmers,” says Steve Heymann, the Massachusetts assistant U.S. attorney who, in the spring of 2010, secured a combined 38 years of prison time for Gonzalez and his co-conspirators for their corporate breaches. “Then we have others, like the C.E.O.’s of AT&T or General Electric, who are extremely good in their area but also know when to go to others for expertise and how to build powerful organizations by using those others. Gonzalez fits into that second category.”
Gonzalez relished the intellectual challenges of cybercrime too. He is not a gifted programmer — according to Watt and Toey, in fact, he can barely write simple code — but by all accounts he can understand systems and fillet them with singular grace. I often got the impression that this was computer crime’s main appeal for Gonzalez.
But he also liked stealing. “Whatever morality I should have been feeling was trumped by the thrill,” he told me.
It seems clear now that Gonzalez didn’t mind betraying people.
When they pieced together how Gonzalez organized these heists later, federal prosecutors had to admire his ingenuity. “It’s like driving to the building next to the bank to tunnel into the bank,” Seth Kosto, an assistant U.S. attorney in New Jersey who worked on the case, told me. When I asked how Gonzalez rated among criminal hackers, he replied: “As a leader? Unparalleled. Unparalleled in his ability to coordinate contacts and continents and expertise. Unparalleled in that he didn’t just get a hack done — he got a hack done, he got the exfiltration of the data done, he got the laundering of the funds done. He was a five-tool player.”
[When sentenced] Gonzalez just leaned forward and peered straight ahead at the judge, as though — the set of his head was unmistakable — staring intensely at a computer.