Given the serious decline in the number of undergraduates majoring in the humanities in general, and literature in particular, teachers of Children's Literature have a unique opportunity to serve their discipline by tapping the power of classroom dialogue to introduce students to the practical reasoning central to humanistic study. This essay takes Long John Silver, from Robert Louis Stevenson's "Treasure Island" ("1883"), as a model for generating lively discussion that begins with literary matters but leads, with help from the teacher, to fundamental questions about the role of the humanities in students' education and in their lives. In the process, the essay traces a pedagogical strategy that moves from matters of plot and character, to issues of ethics and judgment, to larger questions regarding approximate knowledge and sound reasoning about the complexities of the human condition. This inquiry focuses specifically on the charming but villainous Silver and the possible explanations for his escape at the end of the novel. But the ambiguity and fascination of his character are also catalysts for wide-ranging classroom discussion of a kind that Children's Literature routinely promotes and sustains. Such discussion can provide broad, balanced insight into the nature and variety of critical understanding. As such, Children's Literature and the pedagogy it supports serves to identify and enliven the benefits of humanistic study at a crucial moment of academic history.