5. Vladimir Levin
Years active: 1994
Hack Job: When the news reports about Vladimir Levin first surfaced, this Russian was painted as a mathematician with a degree in biochemistry from the Saint Petersburg State Institute of Technology. He stole $10.7 million, and was a hacking genius. Ten years later, one of his accomplices released a memo stating that Levin was more of an ordinary system administrator who managed to get his hands on data about Citibank machines. He reportedly purchased information on hacking the machines for $100 from a group that planned on doing the hack but opted not to follow through. Lenin went nuts with the info.
Total Payout: $10.7 million
Punishment: Three years in jail and $240,015 restitution. Citibank claimed to have recovered all but $400,000 of the lost money.