5. Alex and Rhoda Toth
Married couple Alex and Rhoda Toth won the lottery in 1990, when they were literally broke. The prize was $13 million, and they opted to receive it in payments of $666,666 a year for 20 years, until 2010, which, all things considered, is the smartest move a lottery winner can make. Despite their good intentions, however, things did not work out for them.
They briefly lived it up in Vegas before deciding that the lavish life was not for them, and they returned to their home state of Florida to buy some land and a home. Unfortunately, they were broke by 2006 due to court fees—winning the money had caused a rift in the family that resulted in tons of legal drama and expenses. Alex was even arrested numerous times for growing marijuana plants and for writing bad checks between 2002 and 2005. They were down to living in a tiny trailer on a half-acre of land, their only source of electricity coming from a wire connected to their car's engine.
When they were caught in 2006 for tax evasion, Alex died while awaiting trial and Rhoda claimed that she was too ill to stand trial herself. Turns out, she lied about that too, and when video surfaced of her moving around just fine she was sentenced to two years in prison. And she has to pay $1.1 million to the IRS.