I distinguish between the decision itself and the decision-making process. If you win, you made the right decision, and if you lose, you made the wrong one, and that is true without reference to which decision made the most sense at the time. The decision-making algorithm's job is to give you the highest chance of making the right decision given your prior knowledge, but any such algorithm is imperfect when applied to a vague future. It's perfectly possible to get the right decision from a bad algorithm or the wrong decision from a good algorithm.

Also, when we're discussing things as vague as the intention of an author who is foreshadowing heavily, there's an immense amount of room for judgement calls and intuition, because it's not like we can actually put concrete values on our probabilities. The measure of a person's judgement of such things is how often they're ultimately right, so if he gets it right then I'd have to say that's evidence that he's doing his guessing well. How else are we supposed to judge a predictor? If he's good then he's allowed to put tight confidence intervals on, and if he's bad then he's not. We'll get some evidence about how good he is on Tuesday.