From an early age, William "Bud" Post's life had not been easy. His mother died when he was 8 and his father sent him to an orphanage. From there, he became a carnival worker and held down a series of odd jobs with meager pay that didn't afford certain luxuries -- like home- or car-ownership. But that all changed when in 1998, with less than $3 in his checking account, Post pawned a ring for $40 and spent the proceeds on Pennsylvania Lottery tickets. When he walked away with a $16.2 million jackpot, it seemed as though his luck had changed.
Not so fast. Once word of his good fortune spread, his landlady (and sometime girlfriend) demanded (and received) one-third of the winnings, claiming he'd promised to split the winnings with her after she bought the tickets for him. His brother hired a killer to take Post's life (but only after Post purchased businesses and cars for him and his siblings). Post also made some questionable financial decisions, like buying an airplane he could not fly and a mansion that was eventually sold for parts to erase his mounting debts. To clear other debts, Post sold the rights to his remaining lottery payments, but ended up spending his last $2.65 million on two homes, several motorcycles, three cars, a truck and a sailboat, among other things. He racked up seven marriages, too. "I was much happier when I was broke," said Sullivan.
And just when circumstances didn't seem like they could get worse, they did. Years earlier, in those first, heady months of being a rich man, Post had fired a gun at a bill collector and was charged with assault. Nearly penniless, the lottery winner eventually served the sentence and then lived on a $450 disability payment until he died at age 66, eight years after winning big [source: Sullivan].