This article examines the dynamic between educational leadership in terms of school administration and social studies education pedagogy. The article examines the tension between the mandate for school principals in an age of increased school accountability, and the essence and delivery of social studies pedagogy. The data compiled examine the extent to which the personal political ideology of the teacher influences pedagogy. Utilising an interpretive approach incorporating case study analysis, semi-structured interviews were conducted with seven active and recently retired social studies teachers in Nova Scotia, Canada. The findings reveal that social studies teachers hold a variety of negative opinions regarding outcomes-based models of instruction and, subsequently, take liberties with content outcomes--creating a dilemma with significant administrative implications. This article discusses these findings and offers recommendations for administrators when dealing with teachers who take curricular liberties in the social studies arena.