Abstract The purpose of this qualitative study was to explore the development of urban elementary teacher leaders as captured in narrative data and analyzed through the theoretical lenses of role identity, distributed leadership, teacher leadership and urban teacher leadership. The narratives of five teacher leaders provided rich descriptions that made it possible to: (a) examine possible mechanisms for encouraging leadership assertion choices; (b) identify support practices for encouraging leadership within future teachers in the urban context; and (c) provide insight for building leadership roles in the school environment for those who coordinate professional development activities. Data were collected via semi-structured interviews and post-interview reflections over the course of three months. All of the participants in the study worked in urban settings for the duration of the study and were employed by the same school system in the southeastern United States. Narrative analysis, analysis of narratives and a cross-case analysis strategies were used to reveal participants’ perceptions of individual roles, their journeys of leadership development, and the influences of their experiences in urban contexts on their leadership choices. Recommendations were made to enhance preparation, mentoring, and professional development of potential and current urban teacher leaders.