Heretical Necessity explores the various ways in which an idea of value was established and debated through the literature of mid 19th century America. Above all, it concerns moral value, the language of personal virtue and social ethics; this includes notions of sympathy and self-sacrifice promoted in sentimental fiction, which I read alongside Melville's responses in his later work: the perversion of altruism in Pierre, his critique of benevolence in the short stories, and his ironization of trust in The Confidence Man. Charity is a key issue because it refers both to a notion of fellowship integral to the sentimental vision of society and to a principle of unreciprocated (hence antagonistic) action: giving one's all becomes incompatible with the more measured principles of justice on which a democracy has to be based. I argue that moral value is related to the production of value in the economic sphere, since charity is at once a religious and a financial practice, thus linking the Christian notions of fellowship and giving to ideas of utility and luxury in capitalist society. In this respect my work is informed by the idea of symbolic exchange, via the theories of figures like Mauss, Bataille, Baudrillard and Derrida; prompted by these thinkers, I attempt to identify different types of contract in the literature (commercial, social, masochistic, and literary) and incorporate them in the same general analysis, as a way of exploring the structural complexities of the moral narrative and the discourse of American community.