South Africa is poised at a critical moment in its de/colonizing efforts. Engulfed in laudable anti-apartheid policies and legislation, South Africa has created a strong base for addressing colonial and apartheid legacies of racial, economic and political oppression. Despite these efforts, education continues to be a complex and contested terrain as the new ideology of human rights and social justice for "all" is negotiated, challenged and imagined. What is imperative at this historical juncture is an analysis of how de/colonizing efforts are translated in key educational environments. I present this analysis through the interplay of the de/colonizing narrative of complicity and resistance of Gugu, a Black South African teacher. Contextualized within both historic-political and contemporary educational discourse, rhetoric and legislation, Gugu's narrative offers a space to examine the complex and contradictory roles apartheid and post/apartheid education play in engendering and resisting de/colonization and recolonization. (Contains 11 notes.)