It has become commonplace to describe Machado de Assis's characters and narrators as deeper than those of his contemporaries, and his novels as representations more creatively ambiguous than most literary depictions of nineteenth-century Brazil. In this essay I argue that throughout his novels psychological depth is a function of moral imagination; and a troubled moral imagination is a necessary condition for the literary representation of the modern self. Machado's protagonists are able to fashion the public presentation of their selves by imagining alternatives to their origins, desires, and social predicaments. They have in their pasts a burden the,v need to overcome, and while doing so they find themselves in conditions of freedom and harm. Evil then arises as a consequence of moral dynamism, in solar as it becomes a project for undoing the other. The genesis or a radical conception of free will and evil in Machado's narratives goes back to his translation of Victor Hugo's The Toilers of the Sea (1866). His concern with a more meticulous characterization of inwardness deepens between Iaiá Garcia (1878) and Dom Casmurro (1899), when adopting the structure or a confessional narrative he arrives at a balance between disguised motives (malice), double chronology (nostalgia), and human life as an unfolding, reversible, and self-aware process (metamorphosis). To frame Machado's strategy for depicting moral change, I take from Augustine's Confessions the suggestion that retrospection is the only way of restoring the identity of someone whose self is marked by his or her sense of dissimilarity with the past. Finally, from Kant and Paul Ricoeur I draw the elements for a further consideration of evil as an invitation to think differently about seeing, judging, and narrating human life. [ABSTRACT FROM AUTHOR]