Winning is achieving your ends, not achieving them better than the other guy achieves his.

Also, I'd suggest that you'd improve your analysis if you stopped anthropomorphizing society.

And you should also distinguish between instrumental and epistemic rationality, which I think a lot of people around here should do more of as well. One sense of Rationalists Should Win is I want to Win, and don't want any part of a Rationality that makes me lose. Another sense is Epistemic Rationality helps you Win, which is usually true, but I'm against making a fetish of Epistemic Rationality and treating it as synonymous with Winning.