Brilliant piece on Chicago's woes by Aaron Renn
Speaking of why I have so much respect for the Urbanophile blog (I had the privilege of meeting "Chicago" bloggers Aaron Renn and Lynn Stevens of Peopling Places when I attended the Main Street conference there in 2009-- Lynn and I were going to meet anyway and she brought Aaron along), Aaron has a piece in the City Journal (yes, the publication of the "conservative" Manhattan Institute).
It's on how he sees Chicago's situation--a city deeply in debt, with a shrinking population both for the city and regionally, lack of a particularly strong business sector powering claims to being a "global city," comparatively low per-capita GDP, and its role really being the center city (from the standpoint of center-periphery concepts in underdevelopment studies, although he doesn't cite this work) of the still declining Midwest (with the exception of those areas experiencing booms related to oil and natural gas production).
-- The Second-Rate City?:Chicago’s swift, surprising decline presents formidable challenges for new mayor Rahm Emanuel
He also mentions bureaucracy as stultifying local business development (he doesn't mention contracting, my bicycle facilities systems integration firm ran into the buzzsaw of Chicago contracting last fall), and the failure to systematize laws and zoning practices, but instead preferring the very personal practice of law and action according to "aldermanic privilege" -- kind of like so-called "state's rights" arguments to allow states to do mostly really terrible [and yes, occasionally good things, but very rarely] things like discrimination, instead each Aldermanic district does its own thing, mostly badly. Along with corruption and the power of the political machine, these ways of dysfunction make it hard to re-generate organic growth.
It's kind of a Chicago specific chapter that would be great to include in an update of the book, The Future Once Happened Here, coincidentally authored by a Fellow of the Manhattan Institute, Fred Siegel.
A lot of people criticize Siegel's work, but I think it's not just inciteful but insightful, and if you don't understand what's up, and you're just focused on cheer-leading, you'll never really be able to improve your city and its economic position, in either its metropolitan, regional, or national context.
Likely people will take Aaron's article as personal criticism rather than critical analysis, and the problems present will continue to fester and only get worse.