Volokh.com's David Bernstein on why Obama was friendly with Bill Ayers and Jeremiah Wright

Here's my take: Obama is an extremely ambitious man. He's been interested in a national political career for many years. It's not that surprising that he wouldn't find Ayers and Wright objectionable company—in the very liberal, Hyde Park/Ivy League circles that he's traveled in since attending Columbia, people with such views are more mainstream than, say, the average conservative evangelical Christian. That itself makes Obama far more liberal than the image his campaign attempts to portray.

But what is interesting to me is that not only did Obama not personally find anything especially obnoxious about Wright's radicalism, anti-Americanism, ties to Farrakahn, and so on, or Ayers' lack of regret for his terrorist past, he apparently didn't expect that much of anyone else would care, either. [Emphasis added]How else do you explain why he didn't jettison these individuals from his life before they could damage his presidential ambitions? How else do you explain how his campaign seemed to be caught flatfooted when Obama's ties to Wright and then Ayers became campaign issues? And, perhaps most tellingly, how else do you explain that when Obama was asked in a debate with Clinton about his ties to Ayers, he analogized his friendship with Ayers to his friendship with Senator Tom Coburn, as if being friends with a very conservative senatorial colleague is somehow analogous with being friends with an unrepentant extreme leftist domestic terrorist?[The Volokh Conspiracy - What is the Significance of Obama's Ties to Ayers and Wright?:]

For those of you who think Bernstein is too nuanced, try Kathy Shaidle, who wrote in her blog that

There's nothing wrong with "guilt by association" if the person you're associating with is guilty of something...

The McCain campaign needs to spin the Ayers connection much better.

It doesn't matter when Obama met up with Ayers, or how many meetings they ever had.

It's about the fact that Ayers went from domestic terrorist to "respected community leader", to the point where Ayers was throwing well attended fundraisers for Obama, and they sat on boards together.

Bill Ayers should never have achieved such respectable positions in the first place.

Bill Ayers should be sitting in jail, not on boards! [Obama and Ayers: tenuous, schmenuous]