In The Voice of Liberal Learning, Michael Oakeshott characterizes learning as a strictly non-instrumental activity. In schools and universities, knowledge is acquired for its own sake. Obviously, this liberal understanding of education differs fundamentally from a ‘critical’ notion of education as advocated by Duncan Kennedy and other members of the CLS movement. From a ‘critical’ perspective, Oakeshott’s conception may be seen as yet another attempt – typical for liberalism and conservatism alike – to depoliticize the process of knowledge production and reproduction and to conceal (and thereby to strengthen and legitimize) its effects on the distribution of power, wealth, status and so forth in society. In this paper, the author will confront both views with each other, especially within the context of legal education. The general purpose is to develop a notion of skeptical legal education, which is to a large extent based on Oakeshott’s understanding of liberal learning but which relativizes its insistence on the non-instrumentality of learning and reinforces its critical potential.