This descriptive case study examined how a principal in an urban elementary school in the southern United States became a leader working for social justice in education. The principal cited her parents’ values as contributing to her own seemingly countercultural beliefs and behaviors relating to racial and ethnic diversity, and described schools as essentially middle class phenomena, requiring students and teachers on either side of the class divide to become bicultural. The principal enacted a vision for empowering her students with the same support and freedom of choice available to members of more privileged segments of society. Evidence of interdependent micro, meso, and macro contexts, nonlinearity, and self-organization in the complex system relate the framework of the study to theories of complex systems, offering opportunities to apply understandings of complex systems to the problems of social justice leaders.