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This is such helpful analysis. This season has prompted me to actually take notes (I am not kidding), because the didactic nature of the dialogue is so obvious. I was surprised by it, at first, thinking that the characters would not come right out and say all that they were, making grand summations left and right. But I have gotten used to Chase's straightforwardness this season. And it seems to me Havrilesky is right-- Chase is revealling his true feelings about these characters. In "Philosophy and the Sopranos", the chapter on Tony and Happiness makes the case that Chase holds to the same account of moral psychology as Plato. Chase is giving us the inevitable results of living a life of immorality-- writ large. Even Plato was not this detailed when it came to his description of the psychological devolution that comes from crimes, lies, and the wrong aspirations.
(A smaller point, but finally, with Tony in the previous episode, manhandling Carmela, my insistance that the one liberty Chase took with realism, for the sake of the audience's like for Tony -- Tony's gentleness with women-- finally this has been redressed.)