In recent decades, a number of factors have contributed to the growth of alternative educational programs in urban settings. Public perception of cities as dangerous places and national media attention to high profile incidents of school violence are two influences. Here, Tallerico and Burstyn center on a subset of in-depth interview data provided by the administrative team members responsible for leading and managing alternative school over a five-year period and addresses insights provided by administrative leadership as well as the light that the evolution of alternative schools shed on the opportunities and challenges for administrators of other urban educational system.