Because the category titles are usually fairly complex puns, Watson is built to infer the theme of a category from the questions as it goes along. The humans would benefit from starting at the highest dollar and working towards the lowest dollar, so as to maximize their superior pun skills. I wonder if they'll do that.
IBM also sets a threshold on certainty for Watson answering a question. The machine is perfectly capable of 'howlers', answers that are completely unrelated to the question. These would embarass it if that threshold is too low, and possibly frighten clients of the technology this evolves into. Put the threshold too high, and it might be too cautious to win. I'm sure the tech geeks are mostly interested in winning, but the PR department might be interested in playing with style.
From what I saw, it seems they figured out that that was their best bet (somehow) fairly quickly. Once Watson lost control, the other two lost very little time in going for the big points.
It was mentioned before on LessWrong, but I feel people might appreciate a reminder:
http://www-03.ibm.com/innovation/us/watson/what-is-watson/countdown-to-jeopardy.html
It's a bit of a cheesy PR thing - I'd be a lot more interested if they connected the program on the Internet and allowed anyone to try and ask them general questions, rather than mixing the program with voice recognition and (heh) buzzer-pushing. Trivia tests are also probably one of the easier challenges to deal with, since keyword filtering alone is very efficient in narrowing down the candidate space.
Still, I'm going to watch it if I can: if anybody knows of a streaming link that is accessible to non-US viewers, that would be appreciated.
(Silly aside: is anyone else annoyed by how "Jeopardy" pretends to invert the traditional question-answer format, while what it does is simply moving the "what is" from the former to the latter, even if the result makes no sense? I suppose to US people this is a rather old complaint, but I learnt about the show today and I'm rather bugged by this feature.)