Arendt asks, “Is our ability to judge, to tell right from wrong, beautiful from ugly, dependent upon our faculty of thought?” Her answer is yes, and this chapter argues that this thinking–judging connection is central to her moral philosophy. She derives the connection indirectly, by reflecting on three Socratic propositions: that thinking consists in the back and forth of inner dialogue; that it is better to suffer injustice than to commit it; and that wrongdoing leads to inner disharmony. The chapter examines these, and from this examination it reconstructs Arendt’s argument for the thinking–judging connection. The chapter connects Arendt's and Kant's conception of “enlarged thinking” with Adam Smith’s sympathy-based moral theory. It spells out additional implications that Arendt never drew explicitly, and concludes by comparing Arendt’s views with those of Stuart Hampshire, who believes that inner conflict is in fact “the best condition of mankind,” contrary to the Socratic and Aristotelian moral psychology – an important corrective that requires modification to Arendt’s view.