This chapter examines the cultural-interpretive labor involved in defining right from wrong goods and activities and negotiating the place of possessions, money, and property in the instruction and rearing of children in the latter quarter of the nineteenth century. It is a labor that fell to fathers as well as to mothers, particularly when money was involved. Under such an episteme, and with so much at stake, responses to materiality clustered around a didactic imperative—i.e., the necessity to turn all aspects of child’s life into an instructional course of action. Observers and commentators found virtue and invested in faith in the self-corrective characteristics of simple goods, money (especially in the form of allowances), and the working of notions of children’s property rights. In the process of coming to terms with a growing material-commercial culture and with the inescapable presence of money in middle-class children’s lives, observers, pundits, and advice-givers framed their responses around issues of justice and fairness whereby the child’s subjectivity, its personhood, appears as an increasingly intractable focal point with which to assess the morality of materiality.