As a professor of educational leadership, and a former superintendent of schools, the author understands and appreciates the value and benefit of a positive working relationship between a board of education and its superintendent of schools. Within this context it is important to note that for much of the 20th Century, education was incorrectly viewed as being "apolitical" (Lutz & Merz, 1992). More recently, a number of theories have been formalized in an attempt to better understand the tentative political nature of superintendent-board relations. While these theories help clarify the political nuances of school board-superintendent relations, there is simply not much in the professional literature dedicated to the examination of the historical development of both institutions. Assuming that an historical examination of the complex and problematic nature of superintendent-board relations would improve the level of understanding of both entities, a discussion of their historical development is offered in an attempt to more effectively understand the demands and nuances of each. This paper offers historical perspectives in an attempt to more effectively understand the current status of the institution.