16. Paul Lir Alexander – $170 million
While Alexander was smuggling cocaine into the United States, he worked with the feds to shut down his drug smuggling competitors. He grew wealthier after holding a monopoly in the area, but it all came crashing down when he was arrested and sentenced to twelve years behind bars.
In 2005, he was sent back to his home country of Brazil, where he received a 42 year sentence. In 2011, he left prison on work release, but has since escaped – not looking back.
