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 was published nearly thirty years after his initial engagement with anthropology. While his lectures embodied Kant's 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 and wanted anthropology to play by universal principles if not be totally subordinated to metaphysics. This book is especially interesting from the point of view of border crossing: “In this work Kant comes as close 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 traditions of american pragmatism and Kantian traditions, as in the works of Karl-Otto apel and Jürgen Habermas (as suggested in Chapter One). as we shall see in the case of the master himself (i.e. Kant), Rousseau was a major influence who inspired Kant to use the project of philosophical anthropology for the education of mankind.