This paper utilizes the theoretical framework of complexity theory to compare and contrast leadership and educational change in two urban schools. Drawing on the notion of a complex adaptive system--an interdependent network of interacting elements that learns and evolves in adapting to an ever-shifting context--our case studies seek to reveal the complexities, tensions, characteristics, and related implications for school leadership derived from using this heuristic to understand adaptive change. In particular, we highlight the need to disrupt the status quo as a precursor to adaptive change, the power generated by distributing authority through decentralized networks, the importance of relational trust, and the impact of school culture.