This chapter addresses money's unconscious and emotional resonance and its cultural meanings; money's clinical and theoretical vicissitudes in the context of cultural symbolism and economic change as well as the class position of psychoanalysis and the psychology of class itself; and money's relational meaning in transference and countertransference. In the light of recent psychoanalytic and social thought, money's clinical and theoretical locations turn out to be more proximate than might at first appear. If we put psychoanalysis and politics together, however, what we discern in Freud's heart is the social malaise called 'alienation'. Still, commerce is a cornerstone of the psychoanalytic edifice. The chapter discusses the contradiction between money and love. Money and love, the twin engines that make the world go round, at least the world as we know it, do not go together at all. Love and hate, emerging together, become mutually meaningful in the context of failure.