UPDATE: I originally posted this piece this morning. Now I see that the New Yorker has decided to pair the very serious article that I recommend below with a satiric cover that will get far more attention than the article. I still recommend Ryan Lizza's article wholeheartedly. The cover, not so much.
I'm not ordinarily in the habit of endorsing articles that appear in the New Yorker, but you should go read this piece by Ryan Lizza. Lizza went to Chicago and talked to a lot of the politicians and political movers who were witnesses to the rise of Barack Obama. There are plenty of good bits that I could excerpt, but it's worth the time it takes to read in its entirety. Chicago politics are often quite Byzantine and Rizza does a good job of chronicling Obama's journey through that environment. The piece answers a lot of questions and raises still more. Go get a cup of coffee and punch the link.