The Wicked City is an account of Chicago's vice, crime, capitalism, and corruption from Pierre the Mole, who sold whiskey to the Indians, through Jonny Torrio and Al Capone, who bootlegged a Great Lake's worth of booze during the Roaring Twenties. Chicago's drive for wealth and power in this fifty-year span are evoked through the spirited accounts of the careers of its leading tycoons—such as Charles Yerkes, Marshall Field, George Pullman, and Big Bill Thompson—and its leading the Terrible Gennas, Jim Colosino, Dion O'Banion, Diamond Joe Esposito, Johnny Torrio, and Al Capone. The Chicago portrayed here is raw, real, and vital; its raucousness, lawlessness, ebullience, and greed become poetic.
Who would thought that good ole Chicago was so corrupted in it's early years? (Please detect my sarcasm). It was very interesting reading about Chicago's various power players from the late 1800's / early 1900's like Charles Yerkes, Roger Touhy, Alphonse Capone, Johnny Torrio, Bathhouse John, the Terrible Gennas, Marshall Field, Potter Palmer, etc. Best non-fiction book I've read all year. OK, the only non fiction book I've read all year but I got another Chicago based non fiction book on my plate now: Erik Larson's The Devil In The White City.
So I peeked at the reviews halfway through reading this, because I was finding it frustrating, and a lot of people really like the cynical humor of the prose. To these people, I recommend Nelson Algren's Chicago: City on the Make. Other people liked how accessible it was in terms of historical true crime. To those people -- at least, if they are primarily interested in organized crime -- I suggest Gus Russo's The Outfit. Algren's prose-poem is better-written, and I think significantly inspired the author of this book; Russo's nonfiction book is I think better-researched. I do not have a better recommendation for all the high society goings-on or incidental discussions of music, arts, and sports, but I am reasonably sure they're there somewhere. A good general primer for early Chicago history is Donald L. Miller's City of the Century, but it is definitely dryer and much longer, and concentrates entirely on the 19th century.
Anyway.
My first and largest issue with this book is that it gets very sloppy with facts. Just three examples: 1. the weird claim that probably the first settlers in Chicago were "a gambler [on the run from the law] and a whore" when we actually know the names of the first non-native and part-native settlers in the area; 2. a tired old quote attributed to Al Capone (the one that goes "you get further with a kind word and a gun than a kind word alone," or similar; there's a few variations) which more likely originated from a comedian in the '50s, although it is a good quote, I'll give you that; 3. the implication that Capone bought a 1928-model car in early 1925, which seems like it would be difficult even for Mr. Capone.
So my general feeling while reading the book, when I came across something that was new to me, interesting, and didn't automatically fail my sniff test, was "Oh, I didn't know that! And... I still don't."
My second major issue is that it is frustratingly sexist. You can basically sort the women in this book into Saintly Martyrs and Awful Nagging Wives Who Are Probably Also Spoiled Rich Bitches And/Or Golddiggers. I'm not saying the wealthy women profiled in this book were all great, stand-up people, but it's frustrating when the rich guy is portrayed as a poor hapless sap who has unhappily chained himself to this evil golddigger who is unfairly mad at him for a little cheating every now and then, or otherwise demonstrably being a dick. But of course, it's just a joke; can't I take a joke? I can, actually, but I like them better when they're funny, and Awful Nagging Wives have been done to death.
There aren't a lot of new stories in this book, but they are told in a more interesting style than in many of the Chicago history books I read. The chapters are fairly short and while there is a through line that focuses on the formation of what was to become The Outfit, they also intermix it with a number of other stories from that period. I particularly found the interludes on Red Grange and Louise Armstrong great reads.
I thought the majority of this book was a very good read. I only had two problems. First, there are definitely small inaccuracies which makes it hard to take this book as the only source for any story. For instance, they refer to Capone's activities during certain time periods that don't correspond with evidence provided by other researchers. Nitpicky thing, he refers to the Capone's gang as The Outfit throughout, although from what I've read it wasn't referred to by that name in real life until Nitti's leadership.
The second, and bigger issue, is the last 30 pages. Skip. Skip! Skip!! Basically, the author goes off on his own political agendas. He rants about Bush #1 and Reagan. Specifically HUD and S&L scandles. He rants about Mayor Daley and casinos in Chicago and on his conviction that all handguns should be banned (cause that will drop crime rates!) It's a manifesto for political correctness and bad liberal ideology. Bad because he doesn't think through his arguments fully and they are very easy to see the faults in. Some of it I agree with, he just argues badly.
So, in summary, ignore the last 30 pages and it's a great book to get an overview of Chicago history from 1880-1935. It is especially useful as a more interesting reading addition to a larger library of Chicago history books. (Gangs of Chicago being the first and best)