AliasThe Homeless Hacker
Age: 33

Adrian Lamo gained recognition by breaking into the computer networks of The New York Times, Google, Yahoo!, and Microsoft before he was arrested in 2003. He was known as the "Homeless Hacker" because of his habit of using coffee shops and libraries as his command centers. His hacking caught up to him when he attacked the Times in 2002, gaining access to the personal information of people who've written for the paper, and adding his name to their database of expert sources. After a 15-month investigation by prosecutors, a warrant was placed for his arrest and Lamo surrendered in California. He negotiated a plea bargain that gave him six months of house arrest, and he avoided serving jail time. 

His life after this point hasn't been pretty. He was accused of using a gun on a girlfriend, and was placed in a psychiatric hold in an unrelated incident and was diagnosed with Asperger syndrome. But the biggest controversy of all is that Lamo was the one who reported Chelsea Manning to U.S. authorities after she leaked hundreds of thousands of government documents. His nickname amongst hackers after that was "snitch."