As apartheid ended in South Africa, the hope that its constitution would bring transformative change animated debates over the role of courts and assessment of their reasoning. Having emerged from an era of vicious inequality and discrimination, the Constitution symbolised a project for achieving positive social change based on a new political and moral legal foundation. This new foundation found expression in the idea of transformative constitutionalism. This chapter assesses how courts have explained selected decisions that raise transformative questions, including those around the death penalty, natural resources, employment equity, health care and marriage equality. While courts have extended rights, they have also stated concerns with budgets, or with conflicting concerns in public policy. This chapter suggest that all government organs should perceive constitutional values as the foundation for an egalitarian society, yardsticks for political accountability, and standards for transformative action.