Ludwig Wittgenstein has a recognizable approach that he regularly pursues in his philosophical investigations. There is a problem that he often presses, a form of criticism that he often develops, against traditional pursuits of philosophy. It is surprisingly difficult to say clearly what this problem is. But it is worthwhile to try, for this criticism is not only a hallmark of his thought but is also closely connected to other central features of it, for instance, to his conceptions of language and of the nature of philosophical investigation. These features can be properly understood only in concert with a correct view of his terms of criticism of traditional philosophy. In this essay, Alexander George articulates a problem Wittgenstein sees with philosophy, shows how it illuminates otherwise peculiar features of Wittgenstein’s investigations, and finally considers an interesting situation in which Wittgenstein’s goals might be thwarted.