"Y'know, I actually think Ditka is enough of an audacious choice to run the guy (which would definitely throw Obama for a loop). But the question is what are his positions ? He may be enough to cut into the Chicago ethnic voting bloc dramatically (such as the Rostenkowski-Blagojevich-Emanuel district as well as Lipinski's), which is an absolute must now. At this point, we've got precious little to lose where IL is concerned."
After thinking about it for a couple of days, I have to say that what you say makes a lot of sense. We need to get culturally conservative Chicagoans to start voting GOP if we are to make up for the votes we are losing in the suburbs (since suburban RINOs are increasingly voting Democrat). There are votes to be gained not only in Lipinski's heavily Catholic district and in the inland (Catholic) parts of Emanuel's and Schakowsky's districts (the Lakefront wards are extremely liberal), but also in Gutierrez's heavily Hispanic district (if Mexican-Americans in Cicero can vote Republican in local races, why not for the U.S. Senate?) and perhaps even in some of the black-majority districts (Obama is not culturally black, since he only saw his Kenyan father like once or twice and was raise by his white Kansan mother and white grandparents in Hawaii and Indonesia, and Obama's liberal views are out of step with those of most Chicago blacks, who are very religious and against gay marriage and such tomfoolery). If Ditka can keep it relatively close in Cook County, there is no way that Obama will defeat him, since I would have to assume that Ditka would swamp Obama Downstate.
And oh, as for Ditka's positions, he is 100% pro-life and describes himself as "an ultra-ultra-ultra-conservative" (I meay be missing an ultra there). So we won't have to worry about Ditka being an Arnold-type RINO.
As far as you know, was Glenn Poshard approached about switching to the GOP and running for the Senate? While Obama would beat the conservative Poshard in a RAT primary, Poshard should be able to win in a general election (although Obama would do better in the Collar Counties against Poshard than against a more economically conservative Republican). I read somewhere that Poshard wouldn't switch to run for the Senate, but I don't know whether he had been formally approached.