In his own time, Michael Oakeshott was an important teacher and scholar, one who influenced a generation of students and scholars. Today his work is enjoying something of a renaissance. Considering Oakeshott’s prominence in recent political and educational theory, I think, it is important to reach a full understanding of his work and not allow his conservatism to overshadow his philosophical arguments. By placing his philosophy in its historical context, we can better understand its originality and significance. As have argued here, there are surpassing elements in Oakeshott’s work, and we should strive to hear all the tones of Michael Oakeshott’s unique voice. Michael Oakeshott Has been acclaimed in recent years as one of the most prominent conservative thinkers of the century. E has been called ‘the dominating figure of conservative thought’, and he has been praised for his ‘distinctive contemporary contribution to conservative thought.’ More recently, one scholar has contended that Oakeshott‘s work ‘provides us with what is perhaps the most sophisticated and satisfying statement of liberalism to date’. Oakeshott’s ideas have influenced a generation of political theorists. However, most scholars take Oakeshott to be a fundamentally educational thinker, carrying on a tradition of unique en-cultural thought. Although Oakeshott certainly was a conservative thinker, this approach tends to obscure other aspects of Oakeshott’s work and can lead to an overly narrow understanding of his intellectual procedure. This essay has attempted to focus on an aspect of Oakeshott’s philosophical thought, his critique of technical rationality. I have asked after its origins and connect it to the work of other major philosophers of his era. By looking at Oakeshott in context and studying the evolution of his critique of rationality, we can gain a richer understanding of his work as a whole and better nderstand his place in recent intellectual history.