Chicago
The ratification of the 18th amendment to the Constitution in 1919 made the production and sale (including exportation) of alcoholic beverages illegal in the United States. This ushered in the beginning of what is known as the Gangster Era, a time that roughly spans from 1919 until 1933 when Prohibition was repealed. The 1920s saw gangsters, including Al Capone, Dion O'Banion, Bugs Moran and Tony Accardo battle law enforcement and each other on the streets of Chicago during the Prohibition era. Chicago was the location of the infamous St. Valentine's Day Massacre in 1929, when Al Capone sent men to gun down members of a rival gang, North Side, led by Bugs Moran.
Anti-Italianism
When the United States enacted Prohibition in 1920, the restrictions proved to be an economic windfall for those in the Italian-American community already involved in illegal activities, and those who had fled from Sicily. They smuggled liquor into the country, wholesaled and sold it through a network of outlets and speakeasies. While other ethnic groups were also deeply involved in these illegal bootlegging activities, and the associated violence between groups, Italian Americans were among the most notorious. Because of this, Italians became associated with the prototypical gangster in the minds of many, which had a long-lasting effect on the Italian-American image.