This is an incorrect interpretation of Coscott's philosophy. "Caring really hard about winning" = preferring winning to losing. The correct analogy would be "Caring about [whatever] only in case I win". The losing scenarios are not necessarily assigned low utilities: they are assigned similar utilities. This philosophy is not saying: "I will win because I want to win". It is saying: "If I lose, all the stuff I normally care about becomes unimportant, so when I'm optimizing this stuff I might just as well assume I'm going to win". More precisely, it is saying "I will both lose and win but only the winning universe contains stuff that can be optimized".