The Dynamic Leadership Succession model is used to analyze a leadership succession case in an urban school district. The qualitative findings show that the district did not forecast school leadership needs well; however, the principal sought to develop and mentor teacher leaders as her assistant principals. Second, sustaining efforts within the district were, at times, haphazard, as demonstrated by the two study participants as they were inducted into their respective roles of principal and assistant principal. Finally, the district failed to deliberately plan for leadership transitions.