This essay revisits Michael Oakeshott’s classic cri- tique of rationalism in politics and shows how it is relevant for his understanding of a specific notion of freedom which he associated with the English political tradition. Oakeshott was clear that English freedom must be understood con- textually since it was not the same as German Freiheit or French liberté, both of which were related to ideological, purpose-oriented politics, including enlightened despotism, German Cameralism, French philosophes, fascism and so- cialism. By contrast, the English experience had revealed an economical method of government known as “the rule of law,” which Oakeshott defined as “the enforcement by pre- scribed methods of settled rules binding alike on governors and governed.” English freedom was thus characterized by a procedural way of approaching politics and an absence of overwhelming concentrations of power. By connecting Oakeshott’s essays collected sixty years ago as Rationalism in Politics (1962) with his other works, we can see that the English tradition of freedom was related not only to the ways in which he understood the Whig, libertarian and conservative political traditions, but also to his famous no- tion of civil association (societas) as theorized in his mag- num opus, On Human Conduct (1975). This essay argues in conclusion that Oakeshott’s understanding of civil associa- tion and his criticisms of rationalism can just as easily be applied to the modern right as the modern left.