Alex Koppelman at Salon argues that any October Surprise would be designed to help McCain, not Obama, since he’s the one the terrorists et al. really want to win (to ensure continued war and thus continued recruiting). Maybe, though it sounds a little too clever to me; as Gabe noted, “operatives making plans while dwelling in caves in Waziristan may not have a particularly nuanced understanding of the ebb and flow of American public opinion.”
A reader had this to say: “An October surprise in Iraq will help Obama. An October surprise in the U.S. would help McCain.” I agree with the second sentence, though not necessarily with the first.