Southpaw makes a fair point about pin-gate (OK, it may be too soon to be assigning this "gate" status). And, reasonably, I would agree that Obama probably did mean that it doesn't matter whether a politician wears a flag pin, not that politicians shouldn't wear flag pins.
But, whether he likes it or not, this has become an issue, largely because he is fanning the flames. Had Obama had to face a question from a MSM reporter about the pin recently before he decided to put one on? He is bring attention to the issue and, in so doing, highlighting the remarks from the video in Southpaw's post and highlighting the chasm between him and (here we go again) lower, working class voters. As a reporter, when I see the pin I think, "Man, Obama will really do anything to get these voters. Maybe his problem with them is even bigger than I thought."
One other thought, which is neither here nor there. Could Obama ever risk pissing off some of his support on the way left with stunts like this? There is no doubt that the well-educated far left is infatuated with Obama because, in many ways, he personifies their views (both on politics and on race in this country). Obviously, running against McCain, these voters will vote for Obama. But could there be a backlash if these voters think Obama is compromising his (and their) values?