Why don't you ask him?

Please recite a few of these "mistakes" and "unintelligent comments" you're referring to. The comments you're most likely pointing to are the notorious "bitter" remarks he made. Although it was probably phrased rather poorly, what he essentially meant was that when things are tough and people feel like the government is not listening to them, they tend to cling to the things they are most familiar with, in the context of the discussion he was having, that meant rural white people who hold predominantly conservative views. Understandably offensive, but nonetheless accurate. His flaky associations might be a valid area of concern given that so little is known about him. However, anyone familiar with Chicago politics, (or New York Politics, Miami Politics, and half a dozen other major cities' politics), knows that the political scene is riddled with left wing radicals. If you plan on pursuing a career in politics in this area, there is no avoiding these people. You will associate and interact with a few of them now and again. He served on a board with William Ayers, who was part of the Weather Underground Organization 40 years ago, but Senator Clinton's husband pardoned members of the Weather Underground during his Presidency. Does that mean President Clinton endorsed their political views? No, but the association is much more definitive than Senator Obama's. He had a close relationship with Rev. Wright, which is probably the most radical person he actually DOES know. It may put his judgment in question for consorting with him, but never has anyone produced any evidence to suggest he sought Wright's political counsel. His judgment lies in the foresight he had to be opposed to the invasion of Iraq at a time when nearly 80% of the American population was FOR the war. His judgment lies in a comprehensive healthcare plan to lower premiums rather than impose ambiguous mandates with unclear caveats. His judgment lies in his service on the Veterans Affairs Committee when quite a few other Senators turn the other way when the subject of how we should treat our veterans comes up. His judgment lies in his commitment to have oil industries invest their record profits into alternative fuel development. His judgment lies in his refusal to run a dirty campaign against Senator Clinton when he had more than enough opportunity to given a few things about the Senator's past including a $50,000 contribution from the American Muslim Association that has ties to Hamas, the millions of dollars contributed to her and her husband's library by Dubai, and her participation in an organization that supported the PLO, a recognized terrorist organization. That's where his judgment lies.