Prior to 1994, the South African education system was entrenched by authoritarian leadership in which ultimate authority was vested in school principals and power was not distributed to other members of the school. However, the importance of distributed leadership has increasingly gained prominence across the world. After apartheid in 1994, the government has attempted to educate school leaders on the efficacy of distributing leadership among all stakeholders and its effectiveness on learner achievement. This paper outlines distributed leadership and the need for it in schools. It then unpacks the South African school contexts during apartheid in relation to their management and leadership and considers the extent of departure of the current schools from those characteristics of the apartheid dispensation. The paper argues that, notwithstanding the government's efforts to implement educational reform in the nature of school leadership, the apartheid legacy still lives on, largely because the conditions that characterised the racially segregated schools during apartheid and their influence upon leadership still prevail. Since leadership is shaped by prevailing conditions and circumstances, this paper suggests a need to interrogate the nature of leadership across schools representative of the racial division of schools under the apartheid dispensation.