“Private identity“, “flexicurity“, “representative democracy“, are but three concept that have recently been qualified as oxymora or paradoxes, ie “figures of speech in which apparently contradictory terms appear in conjunction“. The occurrence of legal oxymora is not new as there are hundreds of mentions by judges in case law across the United States alone. In more recent decades, their usage in law and other sciences has been constantly rising in number. Thus the paper first assesses the rising trend of the use of oxymora in legal theory and practice. Second, it discusses the significance of oxymora for legal reasoning as their inherent contradiction appears to pose a serious challenge to dualistic thinking as it is expressed in Robert M. Cover‘s description of the “normative universe“ being constantly created by “a world of right and wrong, of lawful and unlawful, of valid and void“. Finally, the paper concludes by providing useful insights into the future of law and policymaking.