Two of the best books I've read in the past while have been on Chicago and its underclass – Off The Books and Courtroom 302. I'd like to discuss them with you below the fold.
Off the Books is by the sociologist Sudhir Venkatesh. Sudhir immersed himself in a poor unidentified area of Chicago (which is probably the Robert Taylor Homes), and here examines the underground urban economy. He looks at how people get by in abject poverty, forming relationships, making decisions, trading and working. Why do so many legitimate businesses rent out their back rooms to gangs? What are the police and the religious community able to do to help/hurt the causes of the citizens? Why do prostitutes hire pimps?
The tone is academic, and it runs a bit long. However there is something in there for everyone. The sociologists will love the roles people play in their neighborhoods, and how putting on a pastor's robes or a gang-colored hat causes you to accept some responsibilities while negotiating your own means (the sections on pastors "taxing" jobs they get people, or accepting sex from prostitutes are shocking on the first read).
It also has a lot to offer the economist in all of us.
Sudhir worked a lot with Steve Levitt in graduate school, co-authoring the paper that become the "Why do Drug Dealers Live With Their Parents?" chapter of Freakonomics, as well as several other very interesting half-ethnographic, half-economics papers on gang life. These papers (especially that last one), get worked into the discussion.
Some people love the micro-economics of it; how to people manage risk, trade, bargain, and make micro-finance decisions. I love the overtones of macro general equilibrium – even in the poorest parts of America economic forces take control and a status quo develops that is impossible to move without structural change. Asking poor people to break out of this themselves is as silly as thinking I can move gas prices with my mind (or better, by pulling on my bootstraps).
If journalistic writing is more your thing, I can't recommend Courtroom 302 more. It is written by a Chicago Reader reporter name Steve Bogira, and it is the result of Bogira being given one year of full access to a courtroom at the notorious 26th and California courthouse. From the way inmates are treated, to how pleads are encourages, to how interrogations and arrests by the police are handled, to how community concerns play out in the Courthouse, this book pokes its flashlight into every corner.
And what ugly corners there are. Forget Law and Order. Though not at all theoretical (it reads like a series of great investigative reporting), it is very easy to read it this way. The book shows how cynicism rules and how criminal justice is really a Foucauldian matter of managing, collecting and moving bodies. It starts with a chapter on what it is like to get dumped at the holding cells of 26th Street (the chapter is excerpted here, do read it), and from that point forward it is how the system can churn through people like a waste management system.
The book gets a strong blurb from Robert Caro, and in many ways it follows his method of drawing you into strong personalities to look at giant systems.
Bogira gives everyone a voice, and you see how otherwise good (or indifferent) people are caught turning the gears of what comes across as an inhuman and unjust machine. You get to hear all about the torture investigations of the 1920s, and how they are the same shit that goes on in the 70s, and today (most disturbing, you learn about the tradition of getting mentally retarded people to sign confessions, which is evidently easy to do).
You read about a connected mob guy's son beating a 13-year old black kid for walking in white-Bridgeport and how community activists across the city (and country) pressure the case (which ends up in 302).
And lastly you get to see the Kafkaesque nightmare that the War on Drugs has become. This book is incredibly worth your time.