Obama's Willie Horton
One of the nails in the electoral coffin of Michael Dukakis in 1988 was the revelation of Willie Horton (ironically enough first mentioned in a Democratic debate by Al Gore of all people) debacle. Massachusetts had a prisoner furlough program that let inmates out of jail on weekends--even violent criminals like Horton. And predictably while Horton was out one weekend, he raped and murdered a woman. Dukakis refused to halt the program. And it came back to bite him, and deservedly so. The whining Dems have been moaning about racism for twenty years, but the thing that made the ad bite wasn't that Horton was black, it was that it was incomprehensible to people that a program like that, if it existed in the first place, wouldn't be shut down. It just does not compute.
The recent attention being paid to Bill Ayers is very bad news for the very green junior Senator from Illinois. Ayers was a member of the Weather Underground who bombing police stations, the Pentagon, and Capitol Hill. In an interview released on 9/11 (conducted prior to the terrorist attack) Ayers said he "regretted" that they hadn't done more. When the topic came up, Obama said Ayers was just a guy who lived down the street and was a respected part of the Chicago establishment. Well, they're much closer than random neighbors. And while it's true that Ayers is well-connected to the corrupt Daley machine, that is not exactly a credential.
This is going to hurt the hopey-changey unicorn riding candidate. Hooking up with a guy who wishes he had done more to violently overthrow the government of the United States--which he stil today refers to as "the beast"--just does not compute. And I suspect that as more details come out about the closeness of their relationship, it's going to sting a lot.