The Night Chicago Died the U.S. at the height of its popularity because of contractual issues. "The Night Chicago Died" is about a shoot-out between the Chicago Police and gangsters tied to Al Capone. It was inspired by the real-life Saint Valentine's Day Massacre, although that involved Capone's men killing seven of Bugs Moran's gang members and had nothing to do with the police. The song's events supposedly take place "on the East Side of Chicago". Chicago has three commonly referred-to regions: the North Side, the West Side and the South Side. There is no East Side, as Lake Michigan is immediately east of
Saint Valentine's Day Massacre a true detective magazine during the winter of 1935–36. Georgette Winkeler revealed that her husband and his friends had formed a special crew used by Capone for high-risk jobs. The mob boss was said to have trusted them implicitly and nicknamed them the "American Boys". Byron Bolton's statements were also backed up by William Drury, a maverick Chicago detective who had stayed on the massacre case long after everyone else had given up. Bank robber Alvin Karpis later claimed to have heard secondhand from Ray Nugent about the massacre and that the "American Boys" were paid a collective salary of