4. Max Ray “Iceman” Butler

Years active: June 2005—September 2007

Hack job: Butler was a career hacker who went back and forth between "white hacking," where he helped security systems firms secure networks, and "black hacking" projects like a multi-million-dollar credit card scheme that involved stealing 1.8 million credit card numbers.

Total payout: $86.4 million

Punishment: 13 years in jail and $27.5 million restitution