Because the subject of imagination is both complex and can be conceived of in different ways, the focus of the first part of this article is to engage in a descriptive analysis of this faculty. With the help of Greene's intellectual predecessor and former teacher Hannah Arendt, Hannah Spector draws distinctions between imagination and other faculties to get a better grasp of its machinations. Imagination, as this article aims to illustrate, is different from memory or recollection; it is also not the same as divination or forecasting. However, the faculties of thinking and judging are dependent on the fundamental ability to imagine, and thinking and judging are linked to ethical concerns. Therefore these ancillary faculties are addressed as well. Spector also aims to illustrate that imagination can be a dynamic or a destructive force. As such, imagination on its own terms is not ethical. The second analysis turns to Greene's (1995) pre-eminent writings on imagination found in "Releasing the Imagination." This second investigation asks, Why is the imagination important to cultivate in sites of education? What are the possibilities and limitations for the imagination to inspire social change? The third analysis explores Henry Giroux's (2013a) critical pedagogy on the radical imagination and the "disimagination machine." In an age where human beings have increasingly become reliant on technologies to do virtually everything for us, including thinking and judging, the very notion of what it means to live an ethical life is put into question. And ethics deals with questions of value such as: "What is the right course of action to take?" and "How do I know that it is the right course?" These questions are difficult to answer (let alone think about) under conditions that determine thinking and that instrumentalize the learning experience. A way for the mind to step outside of such determinism and instrumental rationality is by engaging the imagination. It is these fundamental questions of ethics and their relationship to the imagination that drive this paper.