In July 1991, infamous Boston mob boss James “Whitey” Bulger hit the jackpot when he won more than $14 million in the Massachusetts State Lottery. Bulger, then 61, bought the ticket with three friends and split the winnings. The liquor store where Bulger purchased the winning ticket was a shop he once owned. Many found his big win unethical but the rules stipulated that “anybody can play the lottery and win” and officials said that the game was not fixed. Bulger has now passed away, age 89.