The purpose of this dissertation is to examine to what extent Sen's freedom-centred view of development, with its existing theoretical foundations, offers sufficient theoretical insights for guiding development policies towards the enhancement of human freedoms. The theoretical part of the dissertation focuses on the three foundational building stones of Sen's freedom-centred view of development. First, the capability approach sets the evaluation space of development in the capabilities that people have reason to choose and value, but by doing so, it is argued that Sen's capability approach contains tensions between human freedom and human well-being that can be loosened by thickening this evaluation space with a substantial view of human well-being. Second, the capability approach views individual agency as central in development, but because of the socio-historical dimension of human freedom and agency, it is argued that concepts of collective capabilities and of socio-historical agency are more central in promoting human freedoms. Third, promoting human freedoms cannot be dissociated from democratic policy-making. But because the link between the two is not necessary, it is argued that the capability approach's consequentialist evaluation of human well-being will have to be thickened by a procedural evaluation which assesses the exercise of political freedom through certain normative principles of decision-making. The empirical part of the thesis illustrates these theoretical arguments through the analysis of two case studies, Costa Rica and the Dominican Republic. The case studies particularly point to a country's socio-historical agency, or collective capability in promoting human well-being, through socio-historical narratives. These narratives assess a country's collective capability in promoting human freedoms by looking at the country's socio-historical reality, and how its members have appropriated that reality in the course of the country's history, opening up or closing down opportunities for realising policy decisions towards the removal of unfreedoms.</p