Oakeshott is known for a critique of modern Rationalism in politics and morals, an ideology which he says derives its inspiration from an exaggeration of the hopes for a universal method of Bacon and Descartes without the (occasional) skepticism of the latter. In this paper, I try to accomplish the following: 1) give a concise statement of what Oakeshott means by “modern Rationalism;” 2) give a summary of his criticisms of it for its baleful effects in politics and morals; 3) show how Oakeshott’s criticisms of it for failing to respect the poetic or creative character of experiential reality are consistent with his philosophic positions in Experience and Its Modes (1933), as well as with his contingent preferences for civil association, understood as he understands it; and 4) give an assessment of the accuracy and reasonableness of Oakehsott’s analysis of, and alternatives to, modern Rationalism in politics and morals.