Before 1890, the area known as Customs House Levee became a gathering place for players and pimps, and was one of the most notorious criminal districts in Chicago.

According to one newspaper,[3] Chicago was at that time considered "the most violent, dirtiest cities – loud, lawless, ugly, offensive, godless; an oversized, stupid village."

In cooperation with the Chicago Outfit, corrupt city councilors "Hinky Dink" Michael Kenna and "Bathhouse" John Coughlin, precipitated the rapid rise of vice in the district.

Among the most famous establishments were: The lowest level of the brothels formed the simple houses in the Bed Bug Row, spanning from Dearborn Avenue and Federal to 19th Street and Archer.

[5] In order to receive protection, Levee inhabitants would attend the biggest event in the district, the annual First Ward Ball.

When anti-vice reformers protested the ball, Kenna justified it as benefiting the people in the district through educational and community programs.

That year, reformers like the Woman's Christian Temperance Union (WCTU) worked towards stopping events like these, claiming that they harmed the families in the Levee.

Increasingly, the public became aware of "white slavery" cases in which girls from rural areas fell into the hands of pimps and were systematically forced into prostitution.

An especially sensational case was that of Madame Mary Hastings, who inflicted torture and forced prostitution on minor girls in her brothel Custom House Place on Jackson Street.

This in turn helped them publish a journal on the stories of women working as prostitutes in Chicago (Levee District), San Francisco, and New York.

[16] The difficult process of closing down the entire Levee District began on January 9, 1910, when Nathaniel Ford Moore died in Victoria "Vic" Shaw's brothel.

A year later, on October 3, 1911, the state's attorney issued warrants for 135 people associated with the Levee, including Big Jim Colosimo, Ed Weiss, Roy Jones and Vic Shaw.

Word spread about corruption in the government, and on October 24, 1911, Mayor Carter Harrison ordered the closure of the Everleigh Club.

The election of Chicago Mayor William "Big Bill" Hale Thompson in 1915 reactivated the illegal business in the Levee.

Due to his Italian origins, Colosimo became the target of Sicilian blackmail bands like the Black Hand Gang (La Mano Nera), which increasingly threatened him.