This article explores briefly the practical as well as theoretical issues that arise when Amartya Sen’s evaluation of justice through the capabilities afforded citizens in a society is applied to postcolonies like Jamaica and South Africa. It argues that the application of the capabilities approach to the circumstances of the postcolony gives rise to the need for an expansion of its purview as the informational focus of Sen’s theory of justice. This is so because of the manner in which domestic as well as external forces and interests function so as to limit in particular the material conditions necessary for freedom and self-actualization in the postcolony. As examples the article engages briefly with the way in which multinationals and multilateral lending agencies in pursuit of their interests have adverse impact upon capabilities in Jamaica and South Africa, affecting in turn the quality of material life, as well as that of democratic governance in both states. In doing so it broaches the important issue of the failure to engage thoroughly with the reality of the limited maneuverability, both at the domestic and also the international levels, that issues from the role of the developing state in the global political economy (as peripheries for the extraction of raw materials, according to Immanuel Wallerstein’s World Systems Theory), which I think haunts the utilization of the capabilities approach to understanding justice and development in the postcolony.