Originally Posted by kane

It actually happened not too long. Bush lost to Clinton in 1992 so it wasn't all that long ago. We also nearly saw it happen again after Clinton. Had it not been for a strange looking ballot and some shenanigans in Florida Gore likely would have won in 2000.

Perhaps in the last 15 years the political landscape has changed enough that it may not happen again for a while, but to me it has happened recently enough that it isn't some kind of historical pattern.