This essay intends to examine the moral character of learning and teaching and the concomitant implications for educational leaders. With the academic curriculum in mind, I ask the basic question: why should young people learn the standard academic curriculum that schools confront them with? Although the expected answer might be, in the present policy context, to prepare them for the increasingly complex and competitive world of work, I answer that it is to prepare them to engage the cultural, the natural, and the historical worlds represented in the academic curriculum -- to engage those worlds as members whose identities are shaped by those worlds, whose futures require skillful and satisfying participation in those worlds, and whose membership impose responsibilities to those worlds. The analysis presents a critique of the decontextualized, abstract, depersonalized learning expected of learners, a learning of right answers to test questions, without any clear understanding or justification of why these answers are "right" -- a learning that is inauthentic, posed, dishonest, and disrespectful, simply a response to the imposed playing of school. I offer a virtuous approach to learning, an approach that seeks the good inherent in the dialogue between the learner and the worlds he or she is studying, a goodness that creates both the intelligibility of the knower as well as the intelligibility of the known found in their mutual interdependence and relationality. The essay concludes with some implications for both teachers and administrators in school that promote this moral, as well as, intellectual character of learning.