Ok, people are just going to keep harping on this aren't they.
First, the weather underground was a little known piece of American History before this mess, especially for the younger generation. Probably very few people here had any idea who the hell Bill Ayers was, and there are probably very few who would be any better informed had you told them he was a member of the weather underground prior to all of this.
So, Barak Obama leaves college and begins working with kids in poverty in Chicago. His is asked to serve on a board. Bill Ayers was also asked to serve on this board. This organization is funded by the well-known republican supporters, the Annenberg family. At this point, the extent of Obama's knowledge about Bill Ayers is probably that he is a highly respected professor of education from the University of Illinois at Chicago, who got his doctorate in education from Columbia. I have seen nothing indicating that his radical views or history were something of which Obama would have been aware.
Forward to 1995. Bill Ayers hosts a getting to know you coffee sit down at his house. Barak Obama attends, making social contacts which it could be said may have helped him launch his political career. At this point, there is still nothing to indicate that Obama would know of Ayers radical past or whether or not he still held radical views. I have working relationships with my colleagues, but I do not know a great deal about their personal histories or philosophies other than whatever topic we are collaborating on. There is no reason to assume Obama's situation was any different.
Now to April 2001. Bill Ayers contributes a whopping $200 to Obama's re-election fund to state senate. Both at the time are serving on the Board of the Woods Foundation, another organization whose goal is to improve education for underprivileged kids. September of 2001, Bill Ayers gives several interviews prior to the release of his memoirs including one in which he makes comments that appear to indicate he still harbors radical ideas and supports violent means to achieve his goals. However, also prior to the release of his memoirs on September 10, he contacted a lawyer who was injured by a WU bomb and offered an apology which the lawyer described as remorseful. This seems inconsistent with one of the incendiary statements he made "I don't regret setting bombs", and "I wish we had done more" which was taken to mean: plant more bombs. As quickly September 15, 2001 Ayers wrote to the Chicago Tribune indicating that though he doesn't deny making those statements, as presented they do not convey the meaning of what he was trying to say. He has maintained since then that he was trying to say that he wished more could have been done to end the war in Vietnam.
He has made statements several other times that could be interpreted as showing a lack of remorse, though he maintains that he has never meant to imply he wishes they had set more bombs. Most recently in June of 2008 Ayers stated that he condemns all forms of terrorism.
Setting aside Ayers claim that his statements were misinterpreted, the information seems to indicate that these revelations of his personal views were made long after the gathering at his home which Obama attended, and even after Ayers donated to the Obama campaign. These statements surfaced in September of 2001 and Obama left the Woods board in 2002, and by most accounts had very little contact with Ayers since 2002.
So, if you want to bring up the question of judgment, I request that you please provide some evidence that Obama was A) aware of Ayers past radical activities, and B) that he was aware that Ayers still had views that support those activities prior to September 2001.
Otherwise, you are accusing him of poor judgment for working on a organization to support education of underprivileged kids alongside a respected professor of education. And the argument does not need to go any further since that is hardly the hallmark of poor judgment.
Furthermore, explain why McCain's connections to the U.S. Council for World Freedom are any less significant.