This article focuses on the larger project of identifying oppressive structures (during apartheid more specifically in this instance) and how educational policy/textbooks (post-apartheid) produce transformative knowledge for decolonization. It presents Black South African teacher perceptions and desires of what/how educational policy, history textbooks can intervene in apartheid indoctrination and what role these have in addressing the nation's meta-narrative of equity and social justice. I take up these teacher narratives as a way to further critique textbooks currently used and examine the written and visual content against post-apartheid decolonizing intentions. Teacher narratives and textbook analysis indicate that even prescriptive post-apartheid textbooks struggle to reimagine history wrought through with colonialism. Decolonizing analysis of visual images in the textbooks show how curriculum policy/practice in South Africa is a collision of anti-apartheid desires and post-apartheid reality. By examining grassroots linkages I attempt to expand the current dialogue on educational policy and textbook studies and to contextualize the field, both historically and contemporarily.