For much of the Twentieth Century, the transition processes of democratizing states have followed a familiar pattern. Outgoing authoritarian regimes relinquished power after extracting the promise of amnesty from the incoming democratic leadership. These authoritarian leaders demanded amnesty for gross human rights violations. The incoming democratic leaders felt like they had no choice. Amnesty has consistently been viewed as a necessary price to pay for democracy. While expedient, in agreeing to amnesty the incoming democratic leaders agreed to sacrifice justice for democracy. This thesis examines the long-term consequences of the amnesty pact on the democratic state and questions whether justice can be sacrificed without ultimately undermining the basis of the democracy. While other studies have focused on the moral implications of amnesty, this work examines the functional realities. Rather than asking whether democratic elites should agree to amnesty, this work asks whether they actually can. Can measures of justice be sacrificed without fundamentally undermining the development and stability of democracy? Can the argument that amnesty is in the interest of the greater good subdue later demands for restoration or retribution? Case study methodology is employed in the examination of the political transitions of Brazil, Chile and South Africa. These countries have each employed different approach to amnesty, though all coming to the same general end. The political and social outcomes in each country speak to the fundamental consequences of amnesty legislation decades after the bargain was struck. The case studies inform my response to the larger theoretical question. This research posits the argument that there are fundamental incompatibilities between the injustice of amnesty and the fundamental requirement of justice that is characteristic of democracy; the current collapse of democracies in Brazil and South Africa, and the fundamental struggles in Chile, are, it is argued, the inevitable results of this impossible trade-off. Building on the data gained from in-country qualitative research, this thesis argues that democratic norms will either be fundamentally weakened by the continued existence and use of amnesty, or, alternatively, democratic norms will be forced to undermine the law or decree itself, compelling leaders to eventually repeal such legislation that ultimately makes democracy, in its basic foundation in justice, impossible. Either situation is highly problematic, creating the potential for instability and the possibility of regime reversal. At its core, this research suggests that the long-term negative consequences of amnesty outweigh the immediate gains made during the transition. For democracy to work, it must be built on a foundation of justice. Amnesty legislation undermines that foundation, and this is simply more than a newly democratizing state can sustain.