Regarding "rationalists should win" - that still leaves us with the problem of distinguishing between someone who won because he was rational and someone who was irrational but won because of sheer dumb luck.

For example, buying lottery tickets is (almost always) a negative EV proposition - but some people do win the lottery. Was it irrational for lottery winners to have bought those specific tickets, which did indeed win?

Given a sufficiently large sample, the most spectacular successes are going to be those who pursued opportunities with the highest possible payoff regardless of the potential downside or even the expected value... for every spectacular success, there are probably several times as many spectacular failures.