A central charge against T. H. Green’s conception of positive freedom is that it confuses freedom and social justice. Rather than illuminating and elucidating the meaning of liberty, Green, so the criticism goes, under the disguise of a definition, recommends social ideals and principles such as social justice. The validity of such arguments is not the focus of my concern. I argue, instead, that contemporary efforts to defend social legislation, the welfare state, and socialism from the claims of negative freedom overlook the important interplay between context, conceptual mutability, and conceptual relationality in the construction of normative political arguments. Green’s conceptualization of positive freedom unveils just such interplay. To reclaim the vital conceptual-normative role of positive freedom in the tradition of liberalism and its contemporary discourse is the task of this paper.