Mathematics education and its links to democracy and development are explored in this article, with specific reference to the case of South Africa. This is done by engaging four key questions. Firstly, the question of whether mathematics education can be a preparation for democracy and include a concern for development, is discussed by drawing on conceptual tools of critical mathematics education and allied areas in a development context. Secondly, the question of how mathematics education is distributed in society and participates in shaping educational possibilities in addressing its development needs and goals is used to examine the issues emerging from mathematics performance in international studies and the national Grade 12 examination; the latter is explored specifically in respect of the South African mathematics curriculum reforms and teacher education challenges. Thirdly, the question of whether a mathematics classroom can be a space for democratic living and learning that equally recognises the importance of issues of development in contexts like South Africa, as a post-conflict society still healing from its apartheid wounds, continuing inequality and poverty, is explored through pedagogies of conflict, dialogue and forgiveness. Finally the question of whether democracy and development can have anything to do with mathematics content matters, is discussed by appropriating, as a metaphor, South Africa’s Truth and Reconciliation Commission’s framework of multiple ‘truths’, to seek links within and across the various forms and movements in mathematics and mathematics education that have emerged in the past few decades.