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Jean-Jacques Rousseau’s critique of Saint Augustine is often viewed in light of his reversal of Augustinian love. While recent commentators have made much how Rousseau’s conception of amour de soi reverses Augustine’s conception of original goodness and the source of human evil, however, little attention has been given to the implications of this reversal for modern democratic views of freedom and law. This paper investigates those implications through an examination of Augustine’s City of God and Rousseau’s Second Discourse. A comparison of Rousseau’s account of amour de soi with Augustinian love of God reveals a profound gulf between the two thinkers’ views of human freedom and the legitimacy of law. Whereas Augustinian love raises skepticism about the free will’s capacity for prideful rebellion against God, Rousseauian amour de soi elevates the free and almost aimless pursuit of one’s spontaneous, self-loving inclinations as contributing to psychic unity or wholeness. These two views of love and freedom culminate in Augustine’s rather positive outlook toward law as a restraint upon the prideful misuse of free will and Rousseau’s seemingly critical attitude toward law as an infringement upon human freedom and a source of our physic disunity. On the basis of these accounts, this paper argues that Rousseau’s reversal of Augustinian love helps clarify and enrich our understanding of the tension between aspects of modern democratic and Christian political thought regarding the status of freedom and law in political life.