The purpose of this article is to explore the relationship between social justice leadership and organizational decision making in order to make recommendations for how principals can make more socially just decisions in difficult school contexts. This article begins with a discussion of social justice leadership, facets and theories associated with social justice, and how facets can be contradictory and problematic in practice. Then, rational choice theory is presented to detail key assumptions and criticisms that are associated with decision-making in complex organizations. Next, rational choice theory is utilized as a straw man for analyzing principal decision-making in complex organizations in order to highlight how competing facets of social justice or inherent leadership dilemmas can arise and complicate decision-making. This article concludes with practice oriented recommendations for principals and other leaders seeking to create more socially just schools.