According to a common reading in the Wittgensteinian literature, William James’s writings, especially the psychological ones, were for the Viennese philosopher a paradigmatic example of conceptual confusion. This chapter argues against this reading, although without minimizing the criticism that Ludwig Wittgenstein leveled against James. More specifically, rather than ascertaining whether Wittgenstein was right or wrong about James, the aim is to figure out what picture of James Wittgenstein offers, and if and in what terms anything specifically Jamesian remains in Wittgenstein’s work. Since it was through the Varieties of Religious Experience that Wittgenstein first came into contact with James, religion is the starting point for this reflection. I will then focus on the pragmatic maxim and Wittgenstein’s comments about the pragmatist conception of truth. The three central sections of this chapter deal with psychology. I will then broaden the discussion to the theme of aspect-seeing, and finally, in the last section, examine Wittgenstein’s observations about the “good” in pragmatism in order to draw some concluding remarks.