In this article I present two theories of historical inquiry, which I characterize as conservative and pragmatic. I argue that these two views of history, John Dewey’s and Hans Georg Gadamer’s, provide an excluded middle between the extremes of positivism and relativism. They are pragmatic insofar as they accept the anti-foundationalist critique of positivism; they are conservative insofar as they refuse to reduce historical inquiry to mere discourse or narrative. Both focus on the situatedness of historical inquiry, paying special attention to the culturally emergent conceptual schemes and prejudices of the historian, but they constrain historical inquiry by providing an improved understanding of the relationship between the problems which give rise to our inquiries and the tools which help resolve them. Dewey, in the key of naturalism, and Gadamer, in the key of phenomenology, provide conservative and pragmatic philosophies of historical inquiry, which refuse to pose as science, but do not fall into narrative fiction. Additionally, their approaches to historical inquiry share a concern for the practical application of the study of history. In this concern for application, both Dewey and Gadamer provide a theory of historical inquiry consonant with a conservative and pragmatic judicial theory, which rejects both the formalism of legal positivism and the model of unconstrained judicial radicalism.