Richard Hatch was the first Survivor castaway to ever outwit, outplay and outlast his way to a million dollars. But that money had a major drawback: he was charged with tax evasion for failing to disclose his winnings (yeah, because it wasn't likely anyone would notice a massive amount of money he won on a top-rated TV show), and thrown into prison in 2006. He's had several stints behind bars in the years since.