Effective school leadership is at the center of educational reform in urban environments. Constituents expect school leaders to transform under-performing schools. However, the educational leadership field relies on traditional ideologies that largely ignore Black principals’ experiences and exclude their voices from politically engaged conversations on leadership. The purpose of this qualitative study was to explore four contemporary Black school leaders’ perspectives of their practices in urban environments. Cultural Historical Activity Theory and Distributed Leadership Theory informed the multiple case study. I employed ethnographic data collection methods of prolonged engagement, interviews (formal and informal), shadowing, documents and artifacts, on-line discussions, field and reflexive journals, and memos, which allowed for crystallization of the data. I adopted and adapted grounded theory and analytic induction to interpret and re-present the Black school leaders’ educational philosophical beliefs, perspectives of traditional preparation, and conceptualizations of leadership that influenced their practices. The findings revealed that the four contemporary Black school leaders from middle and high schools held belief systems that challenged traditional structures and differed from White majority leaders’ beliefs, which aligned with white supremacy and deficit ideologies. The participants thought differently about the purpose of education for all students, especially marginalized groups. These thoughts helped shape their conceptualizations of effective school leadership as an alternative to traditional canons. Their leadership ‘model’ afforded them the ethical latitude to challenge the political sociocultural structure of ‘minimum competency’ standards to afford their students ‘high performance’ school communities. The findings also highlighted traditional leadership programs as ineffective and irrelevant for preparing aspirants to affect substantive changes in contextualized school environments, particularly when the classroom discourse obfuscates issues of equity, race, class, and cultural diversity. Furthermore, the findings revealed participants’ practices, undergirded with moral imperative, humanism, and social justice perspectives, were strategically implemented to dismantle unjust structures. In so doing, they were able to provide students equitable school conditions that allowed them to learn to their highest capacities. Indeed there is the urgent need to include race, ethnic, class, and culturally diverse perspectives in program preparations, policies, and theoretical paradigms to help shape how we think and thus practice school leadership.