Corrupt Chicago and Beyond: Eleven of the Most Corrupt Politicians in Illinois History

Mayor Richard M. Daley

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Like his father (covered in the article below) Mayor Daley was once thought to be considered “Mayor For Life.” In the last few years, however, his influence seems to have been waning. One likely factor is major budgeting problems, pervasive cost overruns in big projects and more than thirty indictments in his Chicago City Hall, indictments which have risen as high as some of his closest aides.

For his part, Mayor Daley has tried to stay above the fray, but has spent as much as two hours being interrogated for information regarding those City Hall indictments a couple of summers ago.

Perhaps the age of double digital percentage victories on election day are over for the Daley dynasty.

Mayor Richard J. Daley

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The original Mayor Daley, the man many considered the consummate big machine politician, was likely the most powerful mayor in the country through most of the 50’s, 60’s and early 70’s. His rule, which is what most of his political opponents would likely call it, extended into national politics, where he is credited with almost single handedly tipping several elections. Whether it was passing out jobs to friends and family for and as favors, or controlling ballot boxes with the “vote early and often” strategy commonly employed in Chicago politics, Daley was the king of kings.

Although much of the hanky-panky involved in Daley’s political career did not come to light until after his death and subsequent biography, his solid reputation remains intact. This is in large part due to the positive changes and reformations that he inspired in the city of Chicago.

Mayor William “Big Bill” Thompson

With Al Capone’s support, William “Big Bill” Thompson once vowed to clean up the corruption and criminal element in Chicago. Apparently this meant that anyone truly attempting to tamp out corruption in the city would be discredited and if not indicted on bogus charges they would at the very least be run out of town.

During Thompson’s tenure as Mayor, bribery and corruption were as common as grass. He was suspected of being on both Johnny Torrio’s and Al Capone’s payroll.

Thompson once debated a pair of live rats that he substituted for his opponents, won one election almost entirely on the basis of reopening taverns where residents could drink until their hearts content. He even went to the extent of launching a very publicized South American expedition to search for tree climbing fish. What else would you expect from a politician whose portrait hung on the wall in Al Capone’s office.

Michael “Hinky Dink” Kenna

One of the “Lords of the Levee” Kenna was a through and through corrupt politicians and one of the masterminds behind the “First Ward Balls” in which politicians and thieves alike paid five dollars for a night of drinking and gambling. Trading food, alcohol, influence, money, and anything else that wasn’t nailed for votes, Kenna earned a big reputation as a First Ward politician.

In 1908 the reputation of the First Ward Ball and the unseemly levels of debauchery that were evidenced gained national attention and brought journalists across the nation to report.

Kenna even once had the audacity to refuse a bribe because it was too big, and then reported the offender to the Mayor’s office with the understanding that small bribes were easier to keep secret and less dangerous to elected officials.

“Bathhouse” John Coughlin

Hinky-Dink Kenna’s longtime partner and cohort, Coughlin was everything that the thin, wispy and quiet Kenna was not. He was a loud, boisterous man who spouted bits of random poetry and dressed in flamboyant, unbecoming attire. The purported mastermind of a prefilled ballot scheme in which they stole ballots, filled as many as they could in to their liking and then dragged drunks, transients and any warm body to the polls to drop them in the box. Coughlin was even brazen enough to pay for these votes, and return the unused ballots to the police for the reward.

The First Ward Ball, an annual party in which one time a drunken Chicago Police Detective shot a fellow officer, and supposedly so full of drunks that a reveler could pass out and never leave his feet for the support offered, shoulder to shoulder, by other drunks, was partly Coughlin’s cause. One for which he earned as much as $50,000 annually around the turn of the century.