I don't think it's far-fetched to wonder if Politico was trying to help Obama in two ways: embarrassing McCain with the question itself, and more importantly by bringing up Obama's house (Rezko) issue during the dog days of August. As Dickerson mentions, the Rezko issue was definitely coming. However, making McCain swing wildly with it now is far preferable to having this ugliness arise in the late weeks of October. The Obama camp had to be hoping that McCain would bring up Rezko now so that when people really focus on the election after Labor Day, it can be dismissed as old news. Politico and McCain opened the door, and Obama pounced, spoofing McCain into dragging out the Rezko issue now.
BTW, the genteel Obama is gone for good - he's too smart (and Chicago street smart) to repeat Kerry's mistakes, especially as his numbers head south. Obama may even pick Hillary as his running mate. As Obama recently said - McCain has no idea what he's in for. Since I detested Lee Atwater, I am loath and a little ashamed to admit that Obama's mission is now "to strip the bark off the little bastard." Obama will have a lot to work with. McCain's ace in the hole is Rezko, but that is an asset that is already beginning to waste.
