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This article examines the evolution of natural law theory and Jean-Jacques Rousseau's contribution to it. The thesis that emerges from that examination asserts that the tension between law in its natural and positive forms is endemic to the human condition. If any common ground is to be found between theories of positivistic and natural law, it lies in the realization that natural law doctrine is not gratuitous and subjective optimism nor idealism pure and simple. The fact that natural law doctrine can serve but a role of general guidance, that it is alien to the concrete, positivistic manifestations of law, constitutes an implicit statement of man's metaphysical dilemma – his inability to fuse the ideal and the real. Rousseau's contribution to natural law speculation lies precisely at this juncture. Unlike his mentors who provided him with the classical natural rights framework in which to build his political theory, Rousseau, as a literary writer and artist, had a particularly acute sense of the dichotomy between the real and the ideal and of the corrosive effects that the intransigent character of reality could have upon the intrinsic aspirations of the individual. His shifting of the classical political discourse to a literary modality reveals in a unique way the ultimate significance of natural law as a theory about law and man.