I was willing to give Obama a pass on his "lipstick on a pig comment." Taken in context, it was clear to me that he was NOT calling Palin a pig. Rather, Obama was inferring that Palin was simply the "lipstick" on McCain's policies. Thus, it was McCain's policies that served as the analogy's "pig."
While one might still disagree with Obama's assessment of McCain's ideas, there was nothing unseemly about his criticism of them. Even so, Obama or his staff should have anticipated that Obama's words would be twisted by his enemies, and Obama should therefore have been advised to make the same point a little more "artfully." With the benefit of hindsight, I bet Obama would have done exactly that.
That's why Obama's latest gaffe, where he mocks McCain for being unable to use email, is all the more mystifying. After all, there's a reason why McCain can't use email--a reason that was documented by the press as early as 2000, and a reason that Obama's staff should have uncovered before the ad ran.
If I was Obama, I'd be chewing some ass right now.