This Article presents a novel understanding of pragmatism in the New Haven School of international law. The New Haven Jurisprudence is wrapped in layers of mystification and the scant accounts of its pragmatism in the literature are either entirely mistaken or only partially helpful, betray a vernacular or truncated understanding of pragmatism, and fail to engage with the internal, epistemic structure of the policy-oriented jurisprudence. In response, this Article uncovers a contradictory form of foundationalist pragmatism in the Yale Jurisprudence in a peculiar relationship between its contextualist and problem-solving promises and its unreflective normative commitments to a set of postulated values of human dignity. In doing so, it foregrounds a 'foundationalist antifoundationalism' and its crippling impact on the pragmatist promises of policy-oriented jurisprudence. Against the worn-out accusations of the New Haven Jurisprudence of U.S. imperialism or disguised affinity with natural law, understanding its foundationalist pragmatism offers a new appreciation of both the genius of Yale’s policy-oriented approach and the promises of pragmatism for policy thinking in international law.