A literary-critical analysis is embarked to show how Matthew highlights the primacy, authority, and exclusivity of Jesus’ role as the Teacher of God’s will and how he features five long discourses in the narrative. Two cultural parallels, the Teacher of Righteousness and Epictetus, are studied for comparison. The ways in which they are remembered in the literature and in which they shape the lives of their followers provide proper historical perspectives and useful frames of reference. Finally, a social-historical reading of the three teachers and their followers, in the light of pertinent sociological theories (sociology of knowledge, group formation), indicates that Jesus the One Teacher serves four crucial functions for his readers in Matthew’s church: polemic, apologetic, didactic, and pastoral.