This memoir essay was originally intended to revisit a time when instructional supervision became the ubiquitous practice in a ‘golden age of supervision,’ and to valorize colleagues who contributed their scholarly canons to the field. An introductory narrative describes the goals and hopes of a field that emerged through Morris Cogan’s popular clinical supervision, and other scholars who adopted and altered his principles with dreams of a road to effective school reform. It tells of the benefits as well as the dysfunctions of practices that occurred over the decades, including the all-encompassing metric world of public schooling. The nightmare includes a technocratic system that provides a view of teaching and supervision dominated by politicians, entrepreneurs, and special interest foundations, and serves a view of schooling based on valuing of cultural uniformity, a punitive notion of accountability, and an uncritical perspective of patriotic nationalism, corporate thinking and class, race, and gender privilege. Foucault’s Panopticon is used as an analytic device for instructional supervision in order to portray a power relationship between the observer and the teacher. Not only does the nightmare reveal what has been happening over the past decades, but it also serves as a cautionary tale for the challenges we are now facing in the pandemic-era schooling of the 2020’s.