The article explores the impact of Michael Oakeshott’s encounter with Aristotle’s virtue of megalopsychia or magnanimity upon his own philosophical pursuits. Although it is in no more than about a dozen pages of his published text that Oakeshott makes direct references to the virtue of magnanimity, it came to play an important part in the formation of his political and moral ideas, not only as a prefiguration of radical individuality, but also as a moral concept which served to reformulate liberal historical discourse and to ennoble the tradition of liberal individualism, as well as to support, along with a set of related ideas, the development of Oakeshott’s own conception of moral conduct. In his work magnanimity is not treated as a virtue of unrivalled excellence that looks down on or threatens the formal and equalizing considerations of justice. In making a twofold move of elevating the tone of the liberal tradition of individuality, on the one hand, and of making the idea of aristocratic nobility more inclusive, on the other, Oakeshott questions the notorious identification of liberal individualism with bourgeois mediocrity, which allows him to reconcile magnanimity and justice within the framework of the nomocratic societas, while offering some significant guideposts towards a possible theory of liberal virtue.