Through the presentation of three historical accounts, this article explores the roles imagination and speculation may play within the writing and study of history. By looking at these three incidents, each drawn from the history and historiography of art education over the past 150 years, through a perspective that embraces the value of utilizing imagination and grounded speculation, it is believed that a reasoned and supported case is made for each of the three historical interpretations put forth. It is intended that by engaging in this process of historical speculation, others in art education will be enkindled to explore the past and read about the history of this field in new and adventuresome ways, thus demonstrating the beneficial roles imagination and grounded speculation may play in generating much-needed historical inquiry and discussion in art education. (Contains 9 footnotes.)