The North Side Gang

In the midst of it all, the Chicago Outfit, one of the longest-running criminal organizations in the land of the free, was perhaps the most notorious of them all. The baleful brotherhood bore a terrifying brand defined by cutthroat competitiveness, sadistic torture tactics, and excessive bloodshed, among scores of other despicable acts. On February 14, 1929, members of the North Side Gang arrived at a warehouse on North Clark Street in Chicago, only to be approached by several police officers. The officers then marched them outside up against a wall, pulled out submachine guns and shotguns, and gunned them all down on the spot. A famous legend is that one of the shot men, Frank Gusenberg, dying from 14 gunshot wounds, told police that nobody shot him. Though Gusenberg's statement is probably apocryphal, nobody opened their mouths. Nobody was ever convicted for the "Saint Valentine's Day Massacre," the most infamous gangland hit in American history, but it's an open secret that it was the work of America's most famous gangster, Al Capone. While the North Side Gang is not as infamous as Capone's mob, the fact that the North Siders were the targets indicate just how powerful Capone's rivals were. Indeed, members like Bugs Moran would carry on a rivalry with Capone that lasted upwards of a decade.