If a thing says “you will win” and this causes you to bet on the Red Sox and loose, then this thing, whatever it is, is simply not an oracle. It has failed the defining property of an oracle, which is to make only true statements. It is true that there may be cases where an oracle cannot say anything at all, because any statement it makes will change reality in such a way as to make the statement false. But all this means is that sometimes an oracle will be silent. It does not mean that an oracle’s statements are somehow implicitly conditioned on a particular world.
Put another way, your assumption that “an Oracle tells you whether you’re going to win your next bet” is not a valid way to constrain an oracle. An actual Oracle could just as easily say “The Red Sox will win” or “The Yankees will win” or whatever.
If a supposed-oracle claims that you will win your bet, and this causes you to bet on the Red Sox and loose, then the actually existing world is the one where you bet on the Red Sox and lost. The world where you didn’t hear the prediction, bet on the Yankees, and won, that is the hypothetical world. So saying that an oracle’s predictions need only be true in the actual world doesn’t resolve your paradox. To resolve it, the oracle’s predictions would have to be true only in the hypothetical world where you did not hear the prediction.
If a thing says “you will win” and this causes you to bet on the Red Sox and loose, then this thing, whatever it is, is simply not an oracle. It has failed the defining property of an oracle, which is to make only true statements. It is true that there may be cases where an oracle cannot say anything at all, because any statement it makes will change reality in such a way as to make the statement false. But all this means is that sometimes an oracle will be silent. It does not mean that an oracle’s statements are somehow implicitly conditioned on a particular world.
Put another way, your assumption that “an Oracle tells you whether you’re going to win your next bet” is not a valid way to constrain an oracle. An actual Oracle could just as easily say “The Red Sox will win” or “The Yankees will win” or whatever.
If a supposed-oracle claims that you will win your bet, and this causes you to bet on the Red Sox and loose, then the actually existing world is the one where you bet on the Red Sox and lost. The world where you didn’t hear the prediction, bet on the Yankees, and won, that is the hypothetical world. So saying that an oracle’s predictions need only be true in the actual world doesn’t resolve your paradox. To resolve it, the oracle’s predictions would have to be true only in the hypothetical world where you did not hear the prediction.