In this essay, the authors reflect on the ongoing teacher effectiveness debate. W. David Hibler is an experienced language arts teacher, who has taught in public high schools and middle schools in Alaska, North Carolina, and New York City. Jeffrey Aaron Snyder is a historian of education who writes about schooling in the twentieth-century United States. Combining their expertise, this essay lines up the personal history of an individual teacher with the larger historical trajectory of the teaching profession to offer a unique perspective on the critical issues surrounding teacher evaluations. The authors argue that student "compliance," on the one hand, and student "engagement," on the other hand, have long been the two key dimensions for evaluating teacher performance. Reviewing the inherent tensions in teacher evaluation initiatives between accountability objectives and the aims of growth and development, the authors conclude that teachers should be assessed with the same care and regard that the best educators devote to assessing their students.