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This essay explores the revival of ancient conceptions of "judgment" in Rousseau's La Nouvelle Heloise. In contrast to the reductionist and potentially irrational thrust of "decision" and "opinion" in modern political theory (e.g., Carl Schmitt), Aristotelian "judgment" does not involve the assertion of a subjective view. Rather, it unfolds as sustained, inter-subjective deliberation that proceeds from a first, subjective perception (gnomē) of a concrete object towards a reasoned grasp (prohairēsis) of its underlying universal form. In ways further emphasized by the later Stoics, especially Seneca (whose work is of major influence on Rousseau), judgment thus presupposes our being "explicit" about the proposition to which we "assent" qua judgment. The intellectualist nature of judgment in ancient philosophy shows its function to be emphatically political, rather than inward and subjective. Though often appraised as the very apex of eighteenth-century sentimentalism, Rousseau's Nouvelle Heloise in fact uses the dialectical structure of epistolary exchange to stage the inter-subjective, deliberative, and increasingly explicit character of judgment. In so doing, it opposes the modern contraction of prohairēsis to an instance of idiosyncratic "choice" or emotively grounded "preference." Implicitly reviving the teleological framework of Aristotelian and Stoic judgment, the exchanges between Julie and St. Preux show judgment to be concerned not with choosing ends but only with assessing whether specific means are commensurable with the meaning of eudaimonia; and the dialectic nature of epistolary exchange is itself crucial in enabling the protagonists to become more aware of the meaning of that end.