14. Richard Hatch
The winner of the first season of Survivor won $1 million. However, when time came to pay his taxes, Richard Hatch stayed on the isle and claimed that the CBS approved to pay his monies. In 2006, he was convicted of tax evasion and was sentenced to a six year prison term. He served only a part of his six year jail term and in March 2011, Hatch returned to his third sentence for not filing his amended tax returns.