Tony 'Big Tuna' Accardo
Tony "Big Tuna" Accardo died — remarkably, of natural causes — at age 86 in 1992. The "reputed" mob boss (he denied holding the position and eluded prosecutors) headed Chicago's Outfit after Al Capone, and upon Accardo's death the director of the Chicago Crime Commission said it was "the end of an era." Accardo may very well have been a gunman in the 1929 St. Valentine's Day Massacre, and he was on Chicago's public-enemy list in 1931. But that was just the beginning of a long, dark career. For decades, he controlled the Outfit, and despite numerous arrests for activities ranging from murder and kidnapping to extortion, union racketeering and gambling, he never served any jail time. A 1960 conviction on tax evasion was overturned on appeal: the Big Tuna (apparently, he once caught a tuna weighing 400 lb., or 180 kg) was slick. He was also aggressive: another of his nicknames, "Joe Batters," alluded to his handling of a baseball bat — and not for the game.