The question that the Jacob Zuma rape trial and its aftermath raised was how a country like South Africa, with such a wonderful Constitution and expansive Bill of Rights, could generate such negative and retrogressive attitudes towards women. In line with this inquiry, this article raises three issues: The first focuses on the legacy of apartheid violence and specifically the cultures of masculinity, the underbelly of apartheid violence. Second, the article explores the findings of the Truth and Reconciliation Commission (TRC), a vital part of the post-apartheid transformation agenda, to examine how the TRC pursued violations of women’s human rights. The third part of the analysis is an examination of the last twelve years of constitutional transformation in South Africa, and particularly the pursuit of gender equality and the eradication of violence against women.