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What's really scary is that this isn't Obama's scariest "friend".

I suspect that Obama's big hug and proclamation of friendship with Kwame Kilpatrick was more political expedience than truth, but it makes for some great attack ads as noted here. While Kilpatrick is definitely an unsavory character and putting a big hug on him strong evidence of poor judgment, Bill Ayers is ten times worse and a much closer friend of Obama.
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