The district-level implementation of a systemic educational change in teacher evaluation mandated at the state level was studied at the elementary and middle school level in a small rural school system. The historical background of teacher evaluation processes from early American schooling to the 1909s was studied. The pilot case study then examined some personal reflections and the experiences and findings of seven principals and five assistant principals. The historical exploration demonstrated a movement from checklists of character traits toward a system that focused on both improved teaching and improved student learning. Personal reflections of one principal suggested that the present evaluation system was a positive reform. Results from the administrators show that paradoxes and contradictions exist inherently within teacher evaluation. The multiple data sources show an awkward and complex process of evaluation. However, the difficult and awkward process results in a more accurate and fair method of assessing how teachers actually affect student learning. The current teacher evaluation system, although imperfect and cumbersome, offers a better process than previously used methods. (Contains 27 references.) (Author/SLD)