Best White-Collar Criminal (2010)
During any other period in South Florida history, Sean Healy would have been a legendary crook. A big Ponzi schemer, Healy had the misfortune of being in a pond with much bigger Ponzi fish. He didn't swindle nearly as much as Palm Beach County's Bernie Madoff. Nor did Healy have the high-flying political friends of Scott Rothstein. But there was an elegant simplicity to Healy's scheme: The Weston businessman asked investors for their money; then he bought stuff with it. Although he was 39 when he got busted, Healy had a 15-year-old's taste in luxury goods. Rap-star bling. A trophy wife from Hooters. An automotive fleet that included a stretch limo, a Lamborghini, a Ferrari, two Porsches, and a Hummer golf cart. Toilets that operated by motion sensor. Statues of superheroes that stood seven feet tall. All told, a Pennsylvania court found Healy guilty of spending nearly $20 million in investor money, for which he was sentenced to 16 years in jail.