Psychoanalytic supervision is moving well into its 2nd century of theory, practice, and (to a limited extent) research. In this paper, I take a look at the pioneering first efforts to define psychoanalytic supervision and its importance to the psychoanalytic education process. Max Eitingon, the “almost forgotten man” of psychoanalysis, looms large in any such consideration. His writings or organizational reports were seemingly the first psychoanalytic published material to address the following supervision issues: rationale, screening, notes, responsibility, supervisee learning/personality issues, and the extent and length of supervision itself. Although Eitingon never wrote formally on supervision, his pioneering work in the area has continued to echo across the decades and can still be seen reflected in contemporary supervision practice. I also recognize the role of Karen Horney—one of the founders of the Berlin Institute and Poliklinik, friend of Eitingon, and active, vital participant in Eitingon's efforts—in contributing to and shaping the beginnings of psychoanalytic education.