Three decades after South Africa’s first democratic election, the country remains the most unequal society on earth. This reflects in part the continuing legacies of apartheid, from access to land, education and employment opportunities to the inability to address the spatial design of apartheid cities and towns. While most agree that this reality continues to detrimentally shape the life opportunities of the majority of South Africans, there is increasing evidence that it is also undermining the post-apartheid settlement – whether in the form of public protests, corruption or simply increasing disillusionment with the political and constitutional order. Since market-led reform policies have clearly failed to produce the necessary redistributive justice required to address apartheid’s legacies, it is time to explore more interventionist options. This chapter proposes a transformational tax to address the legacies of apartheid and to provide the basis for a new social contract that will further the promise of South Africa’s 1996 constitutional order. In exploring this proposal, it employs a comparative analysis of global wealth taxes to reflect on the forms and purposes of a proposed transformational tax.