2. Boss

by Mike Royko

I remember seeing many Mike Royko books on my parents’ shelves when I was growing up, but I never read any of them. Boss was a widely popular suggestion when we were considering new selections for the Book Club, so it was a good opportunity to break my teeth on some Royko and also learn some really good Chicago history. The book focuses on the first Mayor Daley, who ran Chicago for 21 years. His status is legendary and no one in the city could deny his power, even those of us who are too young to have been alive during his reign, but I had no idea that so many of these that I consider permanent city fixtures were actually instituted during his time. The expressways – the Stevenson, the Dan Ryan, the Kennedy, the Eisenhower – were all the results of his efforts. The beautiful city parks, the horrible denial of segregation, O’Hare International Airport, the University of Illinois at Chicago – the good, the bad, and the utterly despicable corruption that has become nearly synonymous with Chicago politics is all a reference to Daley’s six terms in office.

I have to say that I think a lot of the book went over my head and while I do think it serves as an excellent written history of local politics, I had trouble following everything in it. I have no idea what many of the positions in city government do, so when Royko would write about the City Clerk and the Cook County Board and ward bosses and aldermen and county commissioners and so on, I would get kind of lost in all the titles. It made no sense to me why someone in one position taking over another would be particularly scandalous, other than the fact that the Democrats managed to stack the political deck so that their candidates were running virtually unopposed. I didn’t really get the whole thing with a lot of the Republicans being Democrats either, but somehow those running in the Republic party would make it possible for the Democrats to continue leading. In fact, Daley ran for his first position in Illinois legislature on the Republican ballot, but once he was elected he switched sides and worked as a Democrat. I’m unclear as to how this is possible, like, “Oh, just kidding! Not really a Republican!” I’m also still not entirely sure what the term “Machine” means when used in reference to Chicago politics, other than the fact that those in power were able to spin any situation in their favor and get pretty much anything they wanted, right down to passing their positions on to their literal, biological children. While Royko does write very blatantly about what went on behind the scenes of the Daley empire, he does take for granted that the reader is already familiar with this period of political history.

I suppose I wouldn’t recommend Boss to someone who wanted to get some basic, straight history on the city. The book has been criticized as little more than slander (I just learned from Wikipedia that Daley forced bookstores to stop carrying the book, but popular demand brought it back) and Royko definitely takes a side in his biography/exposé, but it’s hard not take a side oneself when presented with the facts. Daley did a lot of amazing and visible things for the city, which makes the racial violence and political dishonesty even more shocking than they’d normally be. I’d like to think we’ve come a long way since then, although it wouldn’t be too difficult to disagree (read Eric Klinenberg’s Heatwave for the more recent antics of Daley the second). I’d recommend a fairly thorough, textbook knowledge of Chicago history before tackling Boss, but I’d still highly recommend it. Lying, cheating, deceit, murder – it’s got all the makings of an excellent story. And it’s one hundred percent true.