Transitional justice pertains to the challenge of reckoning with legacies of widespread or systematic abuses of human rights committed by agents of predecessor regimes. It has become a troubling political issue after a spectacular series of regime transitions in the late twentieth century, and the phrase ‘transitional justice’ today generally refers to a range of measures that new democracies implement to address the issue. There is a vast literature on the subject of transitional justice. However, the majority of research adopts the empirical approach and deliberately eschews the normative issues, and therefore questions concerning the nature of the wrongs that measures of transitional justice are meant to rectify as well as which measures we should adopt in order to adequately address this issue are not answered satisfactorily. In response to this absence of a coherent theory that can address both the past injustice and today’s needs to justify the pursuit of transitional justice, this article attempts to outline a normative theory of this kind by way of an interpretation of Isaiah Berlin’s value pluralism at the core of which is a tragic vision of politics. This theory understands the historical wrongs as a case of tragic value conflict and argues that if the same mistakes were to be avoided in today’s pursuit of transitional justice, we should take seriously the tragic experiences of both the alleged perpetrators and the victims. This value pluralistic theory of transitional justice is of significance to issues like civic education, the implementation of the rule of law and the re-writing of history in the newly-democratized societies. Furthermore, through this attempt this article also hopes to demonstrate that political philosophy is of valuable use to public affairs.