Even assuming that Obama was elected to the Senate in 2000, he would be crushed. Obama's "hope" and "change" nonsense would go nowhere in a country where Bush fatigue has still not set in, and he would be absolutely clueless as to where he stood on the Iraq War. The Bush/Rove campaign would also be unafraid to go after Obama's extreme record or "interesting" background, and he would lose in a landslide. Big Bad Fab probably has the most accurate map, though I would add Oregon and Minnesota to Bush's column.
I agrre, MN and OR are debatable. But more MN than OR, which appears to be more and more strongly Dem since the end of the 1990s.