<P> "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 . </P> <P> 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 Downtown Chicago . While there is an area of Chicago known as "East Side", it is a neighborhood on the Far South Side on the Illinois / Indiana state line . East Side is also several miles away from where Capone lived on Prairie Avenue in Chicago . Furthermore, in the 1920s, East Side was known for being a quiet, residential, and predominantly Eastern European neighborhood--a sharp contrast from the site of the bloodbath described in the song . </P> <P> Songwriters Peter Callender and Mitch Murray said in interviews (most notably on Beat Club shortly after the song's smash success) that they had never been to the Windy City before that time, and that their knowledge of the city and that period of its history had been based on gangster films . (Callender defended his interpretation of Chicago's geography by saying, "There's an East Side of everywhere!") </P> <P> As reported by History.com: </P>

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