It's a wink to the fact that you, the player, are the ultimate driver of the in-game universe. Dead a thousand times, hopeless encounters successfully won - no matter how many times your in-game character fails or is killed, you just reload your saved game and keep playing the game until its conclusion. There is a path/fate mapped out and it comes to pass because you play the game - in other words, you are 'destiny.'
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Or "luck" a la Halo 3.
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Yes. When Cortana says she chose us because we had something the others didn't (luck), it's a similar wink to the player.