How does this interact with the idea that rationalists should win?

Rationalists win more by virtue of having a more accurate model of the world, and clearly this helps only in some domain, while in others only a favorable position in some kind of potential landscape would matter (e.g.: beauty contest). Winning the lottery is one of those cases: buying the ticket is of course bad from a decision theory point of view, but one can always be luck enough to receive a great gain from those bad decisions. In the same way, an irrational person can have a correct belief by virtue of pure luck.