"Education Before Liberation" became the mantra of the struggle against apartheid oppression in South Africa. Apartheid policies predestined the Black majority to servitude and dehumanization. The advent of democracy heralded a plethora of transformative curriculum policies with the express intent to counter the destiny that the Apartheid regime had envisioned for the Black majority. The current curriculum canon which is premised on the tenets of critical pedagogy espouses the ideals of social justice and democracy, and embodies the intent to educate for liberation and social transformation. This article addresses the central question: How do the material tensions of enacting critical pedagogical tenets manifest in post-apartheid South African education through the narratives of educators as transformative intellectuals? In responding to this enquiry, in this article I will (a) sketch an analysis of teachers’ identities as enshrined in retrospective and current curriculum policies; and (b) draw on data from a qualitative study conducted at schools in Johannesburg, South Africa, to explore educators’ personal and professional narratives of pleasure and pain as they persevere in being transformative intellectuals within disadvantaged school communities in an emerging democracy. This article argues that if the ideals of democracy is central to the curriculum for students, then the education system needs to ensure that the personal and professional wellbeing of teachers should form an integral part of the human rights discourse.