Notable Native: Paul Dailing
May 2, 2016
With a passion for history—and a need to earn extra money while working as a freelance journalist—Paul Dailing started hosting Chicago corruption walking tours. The tours run through June, but Dailing said he plans to add more tour dates soon.
Though he said he can write about crooked politicians, bribes and blackmail until he is “blue in the pen,” Dailing thinks taking people to places where corruption has occurred and letting them see it is more moving than reading about it.
The Chronicle spoke with Dailing about his tour, the work that went into it and his plans for future tours.
THE CHRONICLE: How did you come up with the idea for the walking tour?
PAUL DAILING: I’m a journalist, and last year, I wasn’t doing too well on freelancing. I needed some money, so I started doing boat tours. That had been my first job when I moved to Chicago, so I still knew a lot of people. I didn’t realize how much I missed it—interacting with people, sharing these stories—and the tour just kept getting nerdier and nerdier.
I was doing all this research, and I found out people were really reacting positively. I started taking other tours to see about employment after the boats closed, and a couple in particular [really] blew my mind. I started thinking, “The market is open.” People are finding and taking these weird tours. [They’re] interested in nerdier tours—it’s not just Al Capone, pizza and the Sears Tower.
I used to be a political reporter, so this is kind of my area as well. I thought people might be interested in this, and it would give me a chance to tell really important stories that are normally seen as too boring.
What can people expect from the tour?
I talk about Operation Greylord, which is where the feds had a couple people wear wires and report because people were literally buying their way out of convictions; they were literally bribing judges to drop charges. It was a three-year investigation; the feds got the Justice Department to approve bringing fake cases before the judges so that they could offer bribes. The ‘criminals’ were FBI agents playing criminals so they could get judges on tape accepting bribes. There were [also] four governors who went to prison. I talk about them, and I talk about how a blackmailer built the Loop [elevated train cars].
How much work went into creating the tour?
I owe the Harold Washington Library my firstborn child at this point. I can see from where I’m standing a big stack of overdue books. [It took] a lot of research—a lot of work. Some of it was online—the [Chicago] Tribune archives are a fantastic resource. I started doing the preliminary research last year, and then I sort of let it drop for a couple of months and picked it back up. Since I started doing the research I was like, “OK. Barbara Byrd-Bennett.” [The corruption in Chicago] wouldn’t let up.
Why do you plan to add more tour dates in the future?
I will definitely be adding more tours because the response to this has been so positive over the last couple of days. I just didn’t want to book myself for every weekend if people weren’t interested. People do seem to be interested, so there will be more dates coming. This is just side work—I don’t intend to make this my full-time profession—just something I can do to share my city, to educate some people on some issues and help my bills go away.