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How do we develop, learn, and teach moral judgment in ourselves and others? The essays of this dissertation explore insights from Smith and Tocqueville, including how we first come to form a representative within the breast of an impartial spectator to see and judge more impartially; how learning environments can encourage or undermine habits of moral judgment and communication conducive to self-government; and how subtle, indirect communication may invite readers to transcend the mere approval of others more successfully than direct exhortation. The first chapter explores analogies among Smith’s ideas in three types of mental activity: how the mind develops our sense of sight, our sense of moral propriety, and our sense of truth in science or philosophy. In each mental activity the imagination “makes sense” of what would otherwise be an incoherent flux of sense impressions, sentiments, or events by constructing a system of representation and by transporting the self by means of “the fancy” to other vantage points in the imagination, a transporting which, in turn, generates notions of perspective and of impartial spectating in each type of mental activity. Smith’s ideas in his “Of the External Senses” (ES) offer clues as to the nature and origin of his idea of the impartial spectator in The Theory of Moral Sentiments (TMS). The paper concludes by reflecting on how Smith might think about the fact-value distinction in light of the common epistemological structure he thinks is shared by these three types of mental activity. The second chapter examines the centrality of mores in Tocqueville’s approach to political economy and his motif that free institutions are “schools” for the development of mores needed for sustainable democracy. It argues that, to prepare people for self-government, it is imperative not only that the “sciences” of association and self-government be taught, but that the “art” of association and self-government be practiced—either in or outside of formal schooling. It contrasts Tocqueville’s observations of penitentiary systems and of spontaneous association in American society at large as alternate paradigms of education. Finally, it argues that there are tendencies inherent in centralized, top-down bureaucratic control of schooling that tend to generate a “hidden curriculum” that undermines the cultivation of character traits Tocqueville thought necessary for self-government in a democracy and habituates people to the kind of “soft despotism” he thought democracies should fear. The last chapter examines two errors Raphael and Macfie allege Smith made in The Theory of Moral Sentiments about stories found in Cicero. It evaluates the extent to which these alleged errors might be esoteric: one involving Parmenides and Plato, the other involving Ulysses. It argues there is good reason to suspect that the first error is deliberate and contains hidden meaning, but that, in the second case, Raphael and Macfie are mistaken in their claim that Smith erred. Finally, given Smith's discussion of dissimulation, it comments on his probable attitude toward defensive esotericism.