Richard M. Daley, the benevolent dictator of Chicago since 1989, announced last Tuesday (suddenly! shockingly!) that he won’t seek reelection in February. When he leaves office next spring he will have served as mayor five months longer than his father, Richard J. Daley, who died in office just a few days before Christmas in 1976.

In recent months the mayor’s approval rating dropped to around 35 percent as the Windy City’s financial woes escalated. Nevertheless, his reelection to a seventh term seemed all but certain, because according to my sources in the midwest, Daley’s like pizza or sex — even when he’s bad he’s still pretty good.

Back in June, at the annual meeting of the U.S. Conference of Mayors in Oklahoma City, I asked Da Son of Hizzoner, point blank, “What is your secret?” He answered with a question of his own.

“Are you the pizza guy?”

“No, sir. I’m a mayor.”

Maybe I shouldn’t have knocked on his door at the Radisson after midnight. But after I showed him I didn’t have any pizza, and after I took off my lucky Domino’s cap that I wear whenever I’m trying to score an interview with a fellow mayor, and after he got over his confusion and subsequent disappointment — former D.C. mayor Marion Barry had a similar reaction when I showed up outside his hotel room in the late ’90s, though I’d argue he was more relieved than disappointed — Mayor Daley agreed to tell me his secret.



“I planted flowers all over the city,” he explained. “People forget the bad stuff in life if there are a bunch of pretty flowers staring them in the face.”

“Bad stuff? You mean like Chicago having a $650 million budget deficit, or your $1 billion privatization of the city’s parking meters going bust?”

“Here, have a poppy.”

Suddenly I lost my train of thought.

“What was I talking about?”

“How beautiful Millennium Park is.”

“And how! Especially that garden behind the Frank Gehry bandshell.”

“Yes. Thank you. All me.”

“But what about when you bulldozed that private runway in 2003 after the feds said you couldn’t? Or the 47 members of your administration who were convicted of corruption from 2004 to 2008? Or the fact that Chicago was knocked out of the running for the 2016 Summer Olympics in the first round of voting? The first round! Unbelievable.”

“Here, have a bouquet of poppies.”

When I woke up two days later in a beautifully arranged flower bed on Michigan Avenue in Chicago, far from my hotel room back in Oklahoma City, I couldn’t remember a thing, in particular how I got there without any clothes. So I’m glad I had the foresight to tape my interview with Mayor Daley on a handheld recorder I stole from Matt Wardlaw earlier in the year. (Consider it a favor, Matt. Those things weren’t invented so you could record yourself singing “Eye of the Tiger” a cappella when you think no one’s around.)

Still, I don’t blame the mayor for what happened. He’s made of Teflon, and I’d hate to damage that reputation during his final eight months in office. I’ll just assume that the 48th corrupt member of his administration stole my clothes and wallet, but it’s too bad the mystery thief didn’t steal my identity as well, because then I’d be home in Bootleg City while he did the time for my tax crimes in Arizona.

Yeah, I’m corrupt too — so freakin’ what? But I swear by my sixth term I’ll only be mildly corrupt. Now will you forgive me, voters?

This week’s bootleg comes to us from the usual suspect. The usual Bootleg City suspect, that is, not the members of Mayor Daley’s inner circle. Actually, I guess I’m the usual suspect in Bootleg City, but for the sake of argument and expediency, I’m talking about fantasy Survivor frontman Matt Wardlaw, who’s donated a Nada Surf show recorded for MDR Sputnik radio in Halle, Germany, on January 16, 2008. And because a certain “Guest” requested last month that I spend more time talking about the bootlegs and less time talking about my legal hassles, allow me to point out that Nada Surf is a pop-rock trio from New York who almost went the one-hit-wonder route in the late ’90s but came back strong in the past decade with a series of highly melodic—

The guard just announced “lights out,” so I gotta go. Sorry, Guest. Maybe next week …

Concrete Bed
Whose Authority
What Is Your Secret?
Happy Kid
Killian’s Red
Blizzard of ’77
I Like What You Say
Inside of Love
See These Bones
Ooh La La
Always Love
Blankest Year
Meow Meow Lullaby
Imaginary Friends

About the Author

Robert Cass

Robert Cass lives in Chicago. For Popdose he's written under the Sugar Water, Bootleg City, and Box Office Flashback banners and collaborated on the series 'Face Time with Jeff Giles and Mike Heyliger.

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