This paper provides a straightforward argument that demonstrates the irreconcilability of pragmatism and transcendentalism, by way of Darwin’s failure to account for the emergence of the human self or person and the existential and historied import of the human invention and mastery of language. On the Darwinian issue, I examine the implications of Darwin’s having neglected the most important phase of the evolution of Homo sapiens – the invention and mastery of natural language, which account for the self-transformation of the human primate into a self or person (with the acquisition of competences that appear nowhere else in the animal world); and which signify a novel transformation of the evolutionary process itself – the hybrid entwining of biological and cultural forces in the formation of the self. It’s a consequence of the invention of language that accounts for the historied nature of the human form of life. I treat history and historicity as existential constraints on the human form of cognition, which introduces an ineliminable but benign form of skepticism, which I show to be incompatible with Husserl’s transcendentalism and his attempt to accommodate historicity. I take pragmatism to be committed to an existential treatment of history and historicity, in the context of reviewing George Herbert Mead’s analysis of history and historical time. The two arguments converge on the incompatibility of pragmatism and transcendentalism.