Even though both Dewey and Wittgenstein have been rightly classified as both being ‘pragmatist’ thinkers in a broad sense, they stand in stark contrast with respect to their writing style and their general attitude towards the future of western civilization. This article reflects these differences and traces them back to their diverging conceptions of knowledge. Dewey criticizes the philosophical tradition for erecting an artificial barrier between theory and practice, but he retains the traditional high esteem for knowledge by re-describing it as practical inquiry. Consequently, all practically acquired beliefs and certainties are either justified or a potential subject-matter for further inquiries. Wittgenstein, on the other hand, shows the limitation of the very idea of knowledge by pointing to the knowing subject’s fragile relation to its own lived practices. He claims that there are practically acquired beliefs and certainties which are out of reach for the inquiring subject. Thus, the seemingly superficial divergence in style and method shows to be grounded in far-reaching philosophical differences.