A while back, in the immediate post-RNC environment when the race was essentially dead-even, I debated (here and here) whether or not Obama should be doing better. I want to return to his question, but from the other side. Should McCain be doing better, or perhaps better said, could McCain have made wiser choices during his campaign that would have left him in better position to pull off the upset? The answer to that, in my mind, is a resounding yes.
First and foremost was his pick of Sarah Palin. In the very short term it seems to have helped him, but now she is an anchor. In the most recent CBS/NYT poll, she had a 32/41 Fav/Unfav rating, and other polls taken around the same times showed generally similar results; Biden, by contrast, scored 42/21 in that same poll. I think it is pretty obvious that the Gibson interview set them up and the Couric interview knocked them down in terms of turning swing voters away from Palin -- her inane answers dominated political discourse for about two weeks. Further, her obvious idiocy (not her obvious inexperience) is what prevented the McCain campaign from continuing its theme that Obama is not ready. The contrast became brains, not resume, and that is something Obama could readily win. There is also the lost opportunity of putting Palin on the ticket, when he could have chosen someone like Romney. Now, I can't stand Romney (and neither can McCain, apparently) but a McCain-Romney ticket would be much more formidable during a discussion of economics in the eyes of swing voters. Let's say that Obama has a 7 point lead right now -- swap in Romney for Palin, and there is no way Obama's lead is larger and it is quite likely that McCain would be within 3 points.
Let's also examine what McCain has decided to make his signature policy issues. Uh, hmmm... what is McCain's signature policy issue? Perhaps porkbarrelearmarkspending? Drill baby drill? I don't really know, and I know for sure that swing voters don't know. However, you ask me to name one of Obama's signature issues, and I can recall four times (the 3 debates, the DNC), on national TV, that he has looked into the camera and said, "Let me be clear, I want to cut taxes for 95% of Americans. If you make under 250,000 a year, you won't see your taxes go up one dime." [I didn't really look that up, but I betcha that my quote is pretty doggone close] I would not be surprised if far more swing voters can identify that policy with Obama more than any policy associated with McCain.
Another strike against McCain is that he has performed poorly in the debates. He has been cranky, he stumbles over his words, he makes jarring transitions from topic to topic (I swear, last night he started off a sentence talking about William Ayres and ended it with something about strengthening our economy). All polls of undecideds, after all three debates, have shown that Obama won [grain of salt -- I have no idea how good or accurate these polls are, but since Obama's national numbers from reputable tracking polls kept going up, I guess we can conclude that they are not totally off].
I think you add up those three things -- the VP pick, message discipline, and debate performance -- and you could plausibly argue that in an alternate universe, McCain could be close or even ahead. Whether or not that is a knock on Obama (i.e. McCain is losing this race, Obama is not winning it) is debateable I suppose, but the concepts are certainly not mutally exclusive.