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Using urban, suburban, and rural high schools as case studies alongside interviews with nationally identified teacher leaders, this paper examines teacher leadership development for school improvement through a theoretical model. The model was developed from the literature on teacher leadership, work redesign, and organizational leadership. The varied school contexts present different challenges and demonstrate the need for equifinality. Initial findings demonstrate that 1) principal leadership is the single biggest support or constraint related to teacher leadership development. 2) Schools give limited consideration to principal development, school conditions, and the design of teachers’ work to support teacher leadership. 3) The capacity for teacher leadership is associated with teachers’ view of the nature of leadership.