This essay raises three key questions concerning Jean-Jacques Rousseau’s Second Discourse by building on Francesco Toto’s book L’origine e la storia: 1) the theoretical transition to the contractarian paradigm between the Second Discourse and the Social Contract; 2) the problem of arbitrary power vis-à-vis the Discourse’s analysis of despotic rule; 3) the status of capital with reference to the passage from wealth to property in the Social Contract. Through a brief discussion of these issues, the essay intends to stimulate a deeper investigation into both the continuities and the discontinuities between Rousseau’s earlier political thought and his mature contractarianism.