Two-boxing-you is a different you than one-boxing-you. They make different decisions in the same scenario, so something about them must not be the same.
Omega doesn't make its decision solely based on your past, it makes the decision based on all information salient to the question. Omega is an omniscient perfect reasoner. If there's anything that will affect your decision, Omega knows about it.
If you know that Omega will correctly predict your actions, then you can draw a decision tree which crosses off the outcomes "I choose to two box and both boxes contain money," and "I choose to one box and the other box contains no money," because you can rule out any outcome that entails Omega having mispredicted you.
Probability is in the mind. The reality is that either one or both boxes already contain money, and you are already going to choose one box or both, in accordance with Omega's prediction. Your role is to run through the algorithm to determine what is the best choice given what you know. And given what you know, one boxing has higher expected returns than two boxing.
I have read lots of LW posts on this topic, and everyone seems to take this for granted without giving a proper explanation. So if anyone could explain this to me, I would appreciate that.
This is a simple question that is in need of a simple answer. Please don't link to pages and pages of theorycrafting. Thank you.
Edit: Since posting this, I have come to the conclusion that CDT doesn't actually play Newcomb. Here's a disagreement with that statement:
And here's my response:
Edit 2: Clarification regarding backwards causality, which seems to confuse people:
Edit 3: Further clarification on the possible problems that could be considered Newcomb:
Edit 4: Excerpt from Nozick's "Newcomb's Problem and Two Principles of Choice":