This paper explores the history of Shakespeare's influence on the South African educationl, political and philosophical landscape. It addresses the past, engages with the present and envisions the future. It homes in specifically on issues around oppressive violence and silencing, and the role that Shakespeare's texts can play in overriding this. It also engages actively with the current debates around Shakespeare in the South African curriculum, introducing new methods of teaching and assessing Shakespeare that consider the contexts and needs of South African teachers and students. The argument culminates in a focus on the 400 year celebration of Shakespeare's death held on Robben Island in 2016, which featured The Robben Island Bible, a Complete Works of Shakespeare disguised as a sacred text, annotated by political prisoners on the island, including Nelson Mandela.