Sure, it could happen, for either candidate. JFern is correct in pointing out that in 2004, a Kerry win without winning the popular vote was more likely than a Bush win without the popular vote; everyone focuses on the split in 2000, but the Electoral College system actually favored Democrats in 2004 (though it should be noted that my opposition to it is still intact, despite this fact).
The idea that Obama's max in 278 electoral votes is ridiculous. I could easily see him getting up to 350 if the economy continues to suffer. It's not likely that he'll go above 298, but certainly possible. The notion that Ohio is out of reach for Obama is simply silly, however.
Unless there a Dukakis style collapse, I see neither candidate breaking 330 EV's.
