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Adrian Lamo -- nicknamed the 'homeless hacker' due to his delight in using coffee shops, libraries and Internet cafés as his bases, rather than home.
Lamo's claims to fame include breaking into the networks of major organizations. Most of the time, he focused on penetration testing, finding security flaws and reporting findings to the companies that owned them. Lamo broke into the intranet of the New York Times and added his name to their database of experts and gaining access to sensitive information including Social Security numbers.
Other hits included Microsoft, Yahoo!, Bank of America, Citigroup and Cingular.
White-hat hackers are hired for this type of testing -- but Lamo was not. Therefore, after his New York Times break-in, he was ordered to pay approximately $65,000, sentenced to six months of home confinement and two years of probation. Lamo is now working as a journalist and public speaker.