This dissertation argues that political tragedy--the circumstance in which the efforts of political heroes and their people's struggle to effect their societal ideals achieve the opposite outcomes with politically nihilistic consequences--is a feature of the recent attempts to establish viable democratic societies in the postcolonies of Jamaica and South Africa. The political tragedy that it puts forward is in this sense democratic political tragedy. The author examines G.W.F. Hegel's discussion of tragedy as the founding modern example of its treatment in political theory. After addressing its formal, Hegelian foundations, democratic political tragedy in the postcolony is shown to be a telling disjunction between the pursuit of the imperatives of economic growth and immersion in the global economy on the one hand, and the abiding quest for meaningful distributive social justice and national sovereignty on the other. The author argues that popular democratic expectations of the political imagination and creativity of historically oppressed and marginalized populations of Jamaica and South Africa have been aroused by tragic leadership figures. Jamaica under Michael Manley over the course of the 1970s and South Africa under the stewardship of Nelson Mandela from 1994 to 1999 provide the case studies against which the theory is tested. In both instances, the contemporary situation of those countries reveal the tragic course from solidarity and hope to despair under the weight of neoliberal regimes of radicalized inequalities and political disenfranchisement. / Political Science