We meet Adam Osmond, a former gambling addict who spent over 10 years and $1 million trying to win the lottery. He studied for a business degree and bought two convenience stores in Connecticut. Between 2002 and 2008 he started spending thousands of dollars on the lottery, using random numbers from odd sources like a bus sign. Adam's story became even more interesting when he was convicted of printing lottery tickets, but then his life took a strange twist. What happened to his conviction? Did he win back his lost money? Watch this fascinating story unfold.