Between 1520 and 1530 Desiderius Erasmus published several treatises on education in which he provides practical advice about subjects worthy of study and the ideological assumptions which support it. Drawing special attention to his understanding of the natural capabilities of humanity, this article seeks to illustrate the relation between one of Erasmus's theological premises and his promotion of classical culture. During the same period Martin Luther wrote three influential educational tracts and also engaged Erasmus in a debate over the freedom of the will, which forced both the Christian humanist and the Wittenberg reformer to express clearly their understandings of humanity in its natural state. A comparison of their divergent theological positions reveals a fundamental difference in their views of education and its value. Whereas Erasmus justifies the study of ancient secular authors by means of his positive notion of humanitas, Luther subordinates education to the theological rediscoveries of the Wittenberg reformation. The article concludes that further comparative studies of various theological presuppositions and the educational programs they support will advance the understanding of the connections between the ideals and the realities of schooling in sixteenth-century Europe.