It is not transparently obvious why legal theorists are increasingly attracted to the ideas and methods of Ludwig Wittgenstein. After all, Wittgenstein’s writings are notoriously difficult and he said almost nothing, and certainly nothing sustained, about law. And why would self-proclaimed legal theorists be attracted to someone who was quite explicitly hostile to “theory”, who viewed philosophy as a sort of therapy, and who said, famously, “philosophy leaves everything as it is”? But a still more interesting question is, why has Wittgenstein received such curious and conflicting treatment at the hands of the critical legal theorists? On the one hand critical legal theory celebrates Wittgenstein’s work as a key to the dismantling of traditional jurisprudence, but on the other hand critical scholars bemoan his alleged debilitating endorsement of the status quo. It is this last question upon which this essay is focussed.