This article focuses upon monstrously generous teaching styles, enacted in neocolonial educational contexts, where the interactions between students and teachers are sometimes tense and mistrustful. The tensions between students and teachers are explained by discussing the ways in which schools--in the theoretical perspective of Roberto Esposito--operate to immunize the society against youth deemed improper. Utilizing the theories of Antonio Negri, James Baldwin, and W.E.B. Du Bois, the characterization of students as monstrous is discussed and an inversion is suggested, whereby students deemed to be monstrous are considered the source of reinvigorating visions of society. The pedagogical approaches of teachers who seek to welcome and nurture monstrous students are described, relying upon the accounts of great teachers offered by educators and sociologists. In practice, monstrously generous teachers make supererogatory gestures in their interactions with students, as a way of signaling to heavily-armored youth that they are willing to enter reciprocal relationships with them. Once youth drop their armor and begin to share their perspectives, monstrously generous teachers develop multiple means of helping youth develop their worldviews, without surveillance or censor.