Following the collapse of communism in 1989, the Czechoslovak and German governments entered a new phase of relations marked by reconciliatory goodwill. However, relations rapidly deteriorated in the face of mutual claims for material redress concerning the wartime Nazi occupation of Czechoslovakia and the expulsion/transfer of the Sudeten German population in the immediate postwar period. The Czechoslovak (later Czech) and German governments disputed the legal status of the Munich Agreement of 1938 and the Beneš Decrees of 1945, and their differing interpretations had implications either strengthening or undermining the Sudeten German restitution claim. Comparing argumentative strategies reveals a striking symmetry of hypocrisy. Czech and German representatives selectively employed two opposing theories of legal legitimacy, reflecting the jurisprudential schools of legal positivism and natural law theory, either to defend or repudiate the abovementioned instruments. This article argues that reciprocal inconsistency critically undermined attempts by Czech and German representatives to achieve a legal resolution in the 1990s.