This chapter re-examines Jean-Jacques Rousseau's concepts of political freedom and equality, just laws, popular sovereignty, the general will, and democracy. It argues that these concepts have to be understood in light of Rousseau's work as a whole, riddled by the fundamental problem of man's dependence within social relationships, and especially within the social relations on which modern societies are built. This reading acknowledges intrinsic tensions and paradoxes in Rousseau's concepts of freedom and justice, but it also indicates how his approach can nourish a deeper reflection on democracy and its challenges even today. It will thus contribute to the rehabilitation of Rousseau's political thinking that is under way and that points out (inter alia) its relevance to contemporary debates about radical democracy—seen as a space where common laws and rights remain open to be contested by free members of society.