Winners
None spring to mind. Email me if you think of any.

Losers
Yeah, we've got those in spades:

1. George Bush. Campaigning in California and New Jersey? Good grief, you're dumber than we thought (and that's pretty dang dumb). Given the number states in play where you could've spent that campaigning time, this was remarkably stupid. You may get to be prez anyway, but it won't be on the basis of smarts.
2. Al Gore. Leaving Clinton on the sidelines was a huge blunder. Surely given free reign he could've carried at least Arkansas. Put those 6 electoral votes in your pocket and guess what? You're president with or without Florida.
3. Oregon's vote by mail. Wonderfully convenient and loads better than standing in line, but an embarrassing disaster on the vote-counting front. Florida counted their votes twice before Oregon got through theirs once. And Florida is, what, almost four times larger in population? This was a disgrace, to say nothing of the fact that our vote was rendered irrelevant by the Florida situation because we counted so slowly.
4. The media. Easy pickings here: If you don't know for sure who won the state, don't make the frickin' call. Announcing Gore had won Florida (before all the Florida polls were closed), retracting it, announcing Bush had won Florida and was the next president, and retracting it was perhaps the worst series of journalist sins in recent memory. This was "Dewey beats Truman" in electronic form, and it was every bit as effective in reducing trust in the media.
5. Oregon environmental laws and the state budget. Bill Sizemore's Measure 7 aimed to compensate property owners whenever government reduces the value of their land. This means (1) the end of environmental legislation, (2) a $5.4 billion a year hit on the state budget (out of approximately $11 billion), and (3) a big chunk of free change to corporations and wealthy land owners. It's destined for a court challenge and a ballot measure to overturn, but this is a potentially disasterous law for Oregon. Sizemore's been trying to destroy the government. He may have done it.
6. Peggy Noonan. Great speechwriter and hit-or-miss book author. Shrill Wall Street Journal columnist. Missed on the Clinton-Lazio race by quite a bit. Frequently a Bush apologist and not a great one. Needs to stop the Clinton-bashing, however much it might be deserved, and move on to happier topics.
7. The United States of America. If the Florida situation continues spiralling out of control via legal challenges, we could be looking at a constitutional crisis the likes of which we've not faced since the Civil War (not that this is that extreme). Our electoral college, brought into prominent relief, has profoundly confused the people of the world who wrongly assumed that we are a straight democracy. (We're a republic.)
8. Me. My Election Day guesses missed on Delaware (3), New Hampshire (4), Iowa (7), Oregon (7), and Florida (25). That's a difference of +10 electoral votes for Bush and –13 for Gore versus what I projected.
9. The US Supreme Court. The right wing of the Court, in ruling to overturn the Florida Supreme Court, forever dispensed with the notion of judicial restraint as an essential element of conservative thought. The truth is obviously that "judicial restraint" is a convenient cloak behind which hides an ugly ideology. Justice Breyer is right; it'll be some time before the stain of the Court's decision here fades away.