“‘He can’t quit. It’s almost a sickness. If he can, he’s going to hold onto it until he is dead. I’m sure he wants to die in office.’

And why not? He had worked all those years to get it, and it was his, the Machine, the city, and nobody could stare him down.”


Mayor Richard J. Daley at an election campaign rally Feb. 3, 1975. Photo by John Tweedle.

I’ve lived in Chicago for four years, and I grew up in the near West suburbs. I was born in 1987 and from 1989 until 2011, Daley was the mayor of Chicago. It was a big deal when he decided not to seek a seventh term, though I knew I was too young and too new to city life to truly comprehend what that meant. He was part of a legacy I understood even less. The Daley Dynasty. Our longest serving mayor, he served for 22 years, just barely surpassing the previous record holder—his father. Daley, Sr. ran the city from 1955 until his death in 1976. He’s the reason for Richard J. Daley Center, Daley Plaza, and that famous Picasso.

But none of that is what spurred me to pick up Mike Royko’s seminal 1971 biography, Boss.

Illinois politics (really, Chicago politics) have a reputation. Four out of our last seven governors went to prison. Chicago has never really shaken its association with crime from Capone’s heyday, and the number of city and federal officials charged with everything from bribery to extortion isn’t doing anything to change anyone’s minds. And to top it all off, violence in the city remains at an all-time high with at least 82 people shot and 16 killed over the Fourth of July weekend. With stats like that, you can’t help but wonder what the hell is going on.

As a resident of this place for the foreseeable future, I’ve found myself asking a lot of questions. Questions like, why is it like this? How did we get here?

I do my best to keep up with the news, but I wanted more. I wanted some history. I wanted to dig a little deeper.

Enter, Boss.

Royko’s tone throughout was absolutely pitch perfect for me. I tend to prefer memoir to biography because I find the language used in the former to be more engaging or even lyrical, depending on the book. But Boss was able to do just that while still getting straight to the facts. Its first pages set the scene.

A dark Bridgeport street. A quiet red-brick bungalow. A black limousine.

We’re introduced to the indomitable Richard J. Daley as we follow him through a typical day. We meet who he meets. We go where he goes. We see the world through his schedule rather than his eyes. This is how Royko sucks you in.

Once inside, it’s a barrage of names, dates, places, favors, and phone calls. Royko’s playful writing seems to find a kind of joy in unveiling Daley’s inner wheelings and dealings. Whether it’s recounting his infamous outbursts during meetings or the biblical page-long recounting of the nepotism running rampant in the city’s government. Who begat who becomes who hired who. In Royko’s words:

“A Chicago Rip Van Winkle could awaken to the political news columns and, reading the names, think that time had stood still.”

While focusing more strongly on Daley’s reign during the turbulent ‘60s and ‘70s, Royko also does his best to describe the inner workings of what he refers to as “the Machine.” It was the democratic party’s vice-like grip on the city and even the state, and it was a force to be reckoned with—a force I certainly didn’t understand.

When reading, there were times where information was flying at me so fast it was hard to keep anything straight. Between the ward bosses and city officials, between all these terms and names I was hearing for the first time, I occasionally found myself feeling lost. I think non-Chicagoans might find themselves in the same boat, but I don’t think it’s a serious detriment. Royko’s language really does its best to carry you along. It’s as if you’re at a dinner party and he’s welcomed you to a seat at the table even though you don’t know anyone, but it doesn’t matter, because he’s got you by the arm and is introducing you. Before you know it, you find you know enough, even if you can’t remember anyone’s names.

The climax of the book comes in 1968 with the Democratic National Convention. All hell breaks loose and the scene bears uncomfortable similarities with what’s happening in Ferguson today.

Police and demonstrators clash in Chicago on August 28, 1968, during the Democratic National Convention. Photo: ©Les Sintay/Bettman/CORBIS

Police and demonstrators clashed and Daley’s infamous order to “shoot to kill” eventually led to his being forced to testify in court over the conflict.

At the end of the book, I still wished I knew more. It covers a considerable number of years, but I wanted it to keep going. I wanted a part two.

Chicago citizen or not, Boss makes for an entertaining and enlightening read. It’s certainly not the whole picture of Chicago politics, the Machine, or the ‘60s, but it’s an interesting, in-depth look at a man who—like it or not—helped shape both the city of Chicago and the country we live in today.

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