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1.
Commonly referred to on CNN in relation to the Obama presidential campaign, but never explained because journalists are to afraid too explain it. There is a good reason. Chicago politics are incredibly corrupt, dead people still vote, big businesses get "incentives", and friends of the politicians get jobs, money, cars ect. However bad this may sound, Chicago is the city that works, even its corruption works, surprisingly well actually; so much so that people make light of the dead vote, the jobs, and the dynasty like families that run the city. Chicagoans love it, because "Chicago Politics" have produced one of the best, most beautiful, and unique cities in the world where a poor man of mixed race, raised by a single parent can become a world icon.
Lou: What do you mean by Chicago Politics?

Wolf: If I tell you on national TV, its only going to get worse.
by CHIWOLF March 04, 2008
48 29
 
2.
A political environment or arena where any scrawny, half black kid from Hawaii can actually profit quite well from shady business deals in the most corrupt city in America...in a system that makes plenty of money for its downtown political and business leaders and their bankrolled "friends" and for the clean white folks who live in the burbs, but leaves its dirt poor and homeless far behind.
Hey everybody, let's let Chicago politics into the White House...and we'll call it "hope"
by Buddy Knox March 24, 2008
25 47