In this chapter, we explore the challenge of rethinking modernist knowledge by looking at Kant's conception of anthropology. Kant taught courses in both anthropology and physical geography, and his book Anthropology from a Pragmatic Point of View (1798) was published nearly thirty years after his initial engagement with anthropology. While his lectures embodied his crisis of identity as a professional philosopher, thus facilitating a border crossing between philosophy and anthropology, Anthropology from a Pragmatic Point of View was far short of his earlier critique of metaphysics. Kant wanted anthropology to play by universal principles, if not be totally subordinate to metaphysics. The book is especially interesting from the point of view of border crossing: ‘In this work Kant comes as close as possible to combining the qualities of English and continental philosophy. The power of the intellect and the attraction of the imagination both merge into a system of common human concern which has more relevance today then it had before’ (Zammito 2002). The word ‘pragmatic’ in the text is important, and nearly two hundred years later new democratic possibilities seem to have arisen from border-crossing dialogue between American pragmatism and Kantian traditions, as in the works of Karl-Otto Apel and Jürgen Habermas. As we shall see in the case of Kant himself, Rousseau was a major influence who inspired him to use the project of philosophical anthropology for the education of mankind. Thus, Kantian engagement with anthropology embodies several border crossings, first between different intellectual and philosophical traditions, and second between academic philosophy and popular philosophy.