At the close of the 19th century Chicago had a reputation of bad morals, central to which was the 1st Ward, home to a teeming vice district.
It was also home to Chicago's central business district, which would later be called "the Loop" after the looping elevated railroad trackage constructed in it in the late 1890s.
Due to the presence of the Loop the 1st Ward was often known as the "world's richest" ward, a fact which Coughlin would use to fire back at critics of his tenure.
As the first half of the 20th century progressed the 1st Ward would expand southward to also encompass most of the surrounding Near South Side.

At the time of Kenna's ascendancy the vice elements of the 1st Ward and throughout the city were protected by "King Mike" McDonald, who had lived in the city since the late 1850s and controlled its gambling since shortly thereafter, and was credited with first saying "there's a sucker born every minute."
However, by 1890, his reign began to end and a power vacuum started developing.

Corruption was not uncommon in late 19th-century Chicago; aldermen would charge for licenses and infrastructural projects within their wards, a practice known as "boodling".
A group of aldermen including Kenna and Coughlin known as the "Gray Wolves" were particularly infamous for their propensities towards boodling.
Supporters of the pair said that Kenna and Coughlin were unfairly targeted by the reformers and yet reelected by their constituents every election cycle.
At the close of the 19th century Chicago had a reputation of bad morals, central to which was the 1st Ward, home to a teeming vice district. It was also home to Chicago's central business district, which would later be called "the Loop" after the looping elevated railroad trackage constructed in it in the late 1890s. Due to the presence of the Loop the 1st Ward was often known as the "world's richest" ward, a fact which Coughlin would use to fire back at critics of his tenure. As the first half of the 20th century progressed the 1st Ward would expand southward to also encompass most of the surrounding Near South Side.
At the time of Kenna's ascendancy the vice elements of the 1st Ward and throughout the city were protected by "King Mike" McDonald, who had lived in the city since the late 1850s and controlled its gambling since shortly thereafter, and was credited with first saying "there's a sucker born every minute." However, by 1890, his reign began to end and a power vacuum started developing.
Corruption was not uncommon in late 19th-century Chicago; aldermen would charge for licenses and infrastructural projects within their wards, a practice known as "boodling". A group of aldermen including Kenna and Coughlin known as the "Gray Wolves" were particularly infamous for their propensities towards boodling. Supporters of the pair said that Kenna and Coughlin were unfairly targeted by the reformers and yet reelected by their constituents every election cycle.
Michael Kenna