In this book, I have shown some of the limits to traditional approaches to principal leadership in urban schools. I began by describing both the positive assets and harsh social and economic realities within many of low-opportunity communities. I also highlighted how the conditions of today’s urban schools and communities is not a function of poor choices by families or lazy principals and teachers, but rather part of a long and ugly history of racially explicit government policies that have segregated cities and fostered the development of unequal public schools. I used Baltimore, Maryland and El Paso, Texas as reference cities to highlight how racism and segregation denied urban families and students of color from access to healthy food and healthcare, safe communities, employment opportunities, and quality schools. I took further effort to detail more than 200 years of urban school reform, which included how the principal’s role evolved, to demonstrate that top-down school reforms and traditional leadership approaches have rarely provided urban students of color with meaningful opportunities for social mobility. I narrowed in on the social processes and interactions within schools to further demonstrate how traditional approaches failed to meet the needs of students and families. I detailed the work of scholars who have shown how the rituals, routines, structures, policies, and social interactions within many schools frequently work against students of color by failing to value their cultural capital, identities, and assets.