The relationship between regularity and chance, or necessity and contingency, is a common concern of classical pragmatists. The metaphysical quality of this issue flows into the construction of postmodern discourse, although in a very different framework and, paradoxically, under the auspices of the anti-metaphysics that such a discourse claims. This paper proposes at first a brief reconstruction of the chance and regularity issue in postmodernism; then Peirce’s cosmological-metaphysical theory of chance, namely his ‘tychism,’ is recalled as a fruitful suggestion to avoid the conceptual split between chance and regularity. Subsequently, considering the family resemblances between postmodernism and Rorty’s neo-pragmatism, the insistence upon history and contingency that stands out in his work will be tackled as a ‘postmodern tychism’ that, in fact, does not fit too-easy readings according to which he would have turned pragmatism into an extreme form of irrationalism and radical moral relativism. In particular, this paper aims to enlighten Rorty’s effort to re-propose, with new and more refined philosophical tools, the great challenge posed by the classical pragmatists: namely, the challenge to translate the pathos of contingency into an anti-dogmatic ethos, that is a cultural stance that might be able to combine the rejection of absolutes with the commitment to construct meanings and values hosting argumentative interpersonal and intercultural practices as the ‘rule’ of our moral history.