It seems that we are incessantly scolded about the importance of the American political process and its virtue of practicality in contemporary society. Whether through the accumulation of the so-called facts about the issues that inform the veneration of the contest between candidates, the stern and noble duty of becoming an activist performing dreary tasks, or the religious fervor surrounding the sacred obligation of voting, we are assured and reassured that our system is sound and that we must only confront problems of implementation rather than structural ones. From here, the narrative goes that if we subscribe to the doctrine of exclusively employing the efficient, strictly rational, and the immediately realistic, we will almost assuredly succeed in persuading others toward producing the resolutions required to solve our shared challenges. Admittedly, these ideas serve a role in addressing the issues we face. However, when unaided by sophisticated and nuanced notions and applications of the fantastic, the beautiful, the ideal, the possible, the playful, the useless, in a word, dreaming, we foreclose the possibility of building a future that can qualitatively improve society and more meaningfully elevate our being-with-one-another in the world. Therefore, this work aims to validate the aforementioned claim by engaging in a critical, political, and hermeneutic exploration of what it means to dream against the backdrop of present-day American politics. It will honestly seek to analyze the prevailing notions of contemporary western thought and action to work on the way toward a new, yet latent, way of understanding. This understanding would fundamentally revolutionize the task of civilization as being grounded upon the appropriate channeling of our desires and dissatisfactions toward actualizing the projections of our imagination. Simply put, this project seeks to repudiate the mandate of work as toil and order as oppression to clear the way for envisioning a more suitable alternative.