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George "Bugs" Moran inherited the North Side gang in Chicago from Mob boss Dion O'Bannion, and by 1924, became locked in a bloody turf war with Al Capone. The violence between the two bosses climaxed in 1929 with the St. Valentine's Day Massacre, when several members of Moran's mob were brutally gunned down outside of a warehouse.
10 Richest Criminals of All Time
A life of crime typically doesn't pay off for very long. From drug kingpin Pablo Escobar to Chicago mob boss Al Capone, most of the worst criminals in the world are eventually captured or killed.