In the last decade or so, political realism has become a fashionable phrase to describe a new (or, perhaps, rediscovered) understanding of political theory. Many otherwise disparate thinkers, either willingly contributed to or have retrospectively been thrown into what one of the scholars has likened to a community stew. Among the latter, Michael Oakeshott is highly interesting, given one of the central tenets of contemporary political realism is a reworking of the relationship between politics and philosophy, which Oakeshott famously vehemently rejected. In this chapter, the author considers Michael Oakeshott in relation to contemporary political realism, not primarily because interpreting him as a political realist would enable us to understand him better (though, incidentally, it might), but because, his understanding of the modern political predicament can potentially shed new light on the nature of the relationship between political theory and political practice, which is still a matter of controversy among contemporary realists.