Here's a great article, courtesy of National Review, on the issues before the Supreme Court in the case that seeks to ostensibly "ban" gerrymandering. More or less, it seeks to enshrine the principle of "proportional representation" so that states can be compelled to get a bunch of districts which are split about as evenly as possible between supporters of either party. Historically, on the other hand, districts were chosen to be as homogeneous as possible--with the result that the choice in many districts choose "which kind of Republican or Democrat" instead of a Republican or a Democrat.
There are two graphs which illustrate the problems. First, you've got the lines in Wisconsin, which follow city and county boundaries pretty well and are reasonably geographically compact. The other example is the gerrymanders of Chicagoland, where inner city neighborhoods are lumped in with the suburbs, and city and county boundaries are not honored.
I can see a bunch of problems with Chicago's plan, starting with the fact that suburban residents in Illinois District 1, might not feel safe campaigning in most of the district--and the district's length (40 miles in Chicago traffic) makes campaigning difficult for all. The next objection is that it really prevents people who differ politically from gaining office; both the South Side of Chicago and the far more conservative suburbs and rural areas in the district are cheated this way.
Finally, it's worth noting that when districts are fairly evenly divided between the two major parties, that increases the likelihood that precincts like Burr Oak will decide elections--always a problem in Chicagoland, sad to say.
Really, what's at stake here stems mostly from the fact that many on the far left cannot even stomach the possibility of living in our midst, and thus segregate themselves into urban and university enclaves. So while they tend to elect Minnesota's state bird, there are far fewer than there would be if leftists could learn to tolerate others.
Hopefully the Supreme Court makes the right decision, and helps keep the loons in the lake where they belong.
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