Just to follow up on Chris's post, I actually think George Will's love of driving and hatred of Portland makes sense.
First, if you've spent a considerable amount of time around Connecticut Avenue in Upper Northwest D.C.--as I did growing up--then it's possible, maybe even likely, that at some point you've witnessed Will being a very agressive driver. (In my experience he was hard to miss; if memory serves, he drove a Chrysler Lebaron convertible, but don't hold me to that.)
Second, if you've ever driven in Portland, then you know that the few people out there who do choose to drive instead of bike or take the light-rail are extremely defensive drivers. So defensive that when I lived out there for a summer and one day, while trying to drive down Division Street, had the temerity to toot my horn at the person in front of me who'd already failed to move through one green light and was now about to sleep through a second green light cycle, I was chastised by the person in the car behind me for being an asshole. Evidently you're not supposed to tap your horn until the person in front of you has sat through at least three light cycles. Try pulling that stunt in Boston, where you'll get your bumper tapped if you're not moving .5 seconds after the light has turned.
Anyway, I have no idea if Will has ever been to Portland, much less driven there, but if he has, then I can safey predict that it wasn't a happy experience--for either Will or Portland.