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Chicago Corruption Isn’t Cute: Walking Tour Highlights Dark Side of Political Graft

The tour’s creator is sick of your souvenir Al Capone T-shirts.

The Chicago Corruption Walking Tour   Photo: Colleen Kujawa

Paul Dailing was fed up with the folksy and unaffected way people talk about Chicago corruption—think Al Capone T-shirts and the bemused smirk as people shrug and say, “That’s the Chicago way.”

The reality is corruption in Chicago has ruined untold numbers of lives and led to the untimely end of many of them. To remind people of this reality, albeit in an enlightening and entertaining way, Dailing combined his experience as a newspaper reporter, a journalism professor, and a riverboat tour guide to create a unique walking tour about political corruption in Chicago and Illinois.

“People don’t realize the actual cost of all of this,” Dailing says. “I want them to know that even though people love Richard J. Daley, if you were black, he wasn’t a great mayor. If you were gay, or a woman, or poor, or a hippie, or just not his friend, he was terrible. This stuff gets romanticized for some lousy reason.”

The Chicago Corruption Walking Tour begins aptly outside the Metropolitan Correctional Center, moving north with stops at the Dirksen Federal Courthouse, the Marquette Building, Thompson Center, one of our excessively expensive parking meters, a ritzy strip of River North that’s somehow in a tax increment finance, or TIF, district, and other downtown places to highlight key moments of unscrupulous power moves. Even people who’ve lived in Chicago their whole lives will learn something, Dailing promises.

“Capone’s men chased Octavius Granady [a black aldermanic candidate] through two wards before shooting him to death,” he says. “That was among the more disturbing stories I found while researching for the tour.”

Dailing’s topics range from seemingly outrageous (former mayor William Hale “Big Bill” Thompson threatening the king of England, the Chicago Outfit gangsters who also were aldermen) to all-too-familiar stories, like which four of our governors went to prison and which others were just criminally charged. He even uses maps to illustrate the most egregious examples of gerrymandering—like in the 4th district, where a stretch of highway where no one lives somehow connects two distinct areas.

Tours start Sunday, May 1, and spots can be reserved online. A mile-long tour is available for $15 and the full 2.25-mile tour costs $25. Half of the tour revenue goes to City Bureau, an organization that trains young journalists covering the south and west sides to create meaningful journalism that is published in local and national outlets (including this one).

One of the running themes throughout the tour is that it’s not always clear who’s bad and who’s good—"It’s a fluid issue,” Dailing says. Former U.S. Attorney Patrick Fitzgerald, for example, may have sent disgraced former governors George Ryan and Rod Blagojevich to prison, but he also threw reporters in jail during the Scooter Libby/Valerie Plame affair.

Al Capone, center, with lawyers in federal court in Chicago during his 1931 tax-evasion trial. Photo: Chicago Tribune historical photo/Herald&Examiner

“I think Otto Kerner was a great governor, except for the fact that he took bribes,” Dailing adds. “The Kerner Commission report delved into the race riots, and it was the first time the U.S. government admitted social inequality is a real thing.”

It gets even murkier at the turn of the century when 1st ward aldermen Michael “Hinky Dink” Kenna and John “Bathhouse John” Coughlin came to power. While they helped poor citizens find better jobs and services, they also gave people free drinks at a bar in exchange for votes and used their influence to line their own pockets. 

“They were basically scumbags for the people,” Dailing says. “But guys like Hinky Dink and Bathhouse also made things difficult for people who didn’t fall in line and vote the way they were told. Buying beers for votes is cute, but I try to show this in terms of a larger picture where things get worse, and suddenly these people aren’t so cute.”

Dailing says he hopes people leave the tour a little angry, a little more skeptical, but ultimately more aware of the extent to which corruption shaped Chicago and Illinois.

“I don’t want people to leave this thinking it’s a hopeless situation,” Dailing says. “We know these stories because these people failed. The patronage system has been whittled down from the height of where it was, same with the Chicago Outfit. People are wising up that TIFs are bad politics.”

Political satire shows like The Daily Show with Trevor Noah, Last Week Tonight with John Oliver, and Full Frontal with Samantha Bee are popular even though they point out sad-but-true aspects of the way the world works. With that in mind, Dailing hopes people enjoy the tour but also are upset enough to get more involved with local political processes.

“I do want people to be pissed off and to want to do something about it,” he says. “I also want people to have a different Chicago experience. It’s OK to marvel at how tall the Sears Tower is, but we have more to talk about here.

“And screw all the romanticizing of Al Capone. We don’t need an unhinged gangster killer on T-shirts.”


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