Saint Valentine's Day massacre
Al Capone was the most powerful bootlegger in Chicago. By 1929 he had eliminated several of his rival crime bosses. The last one on his "list" was Bugs Moran. Capone was trying to appear as if he was retired to Florida. So Capone didn't want to be seen as starting another gang war. Instead, Capone gave the order to one of his associates, Jack McGurn, to eliminate Bugs Moran.