Cape Town is home to a series of extreme disjunctive arrangements of wealth and poverty. Key to understanding the city is the deep inscription of historical injustice and its expression in contemporary forms of social injustice. In the paper that follows, we report on conversations with four indispensable commentators on the contemporary state of the city: artist Thania Petersen, architect and artist Ilze Wolff, museum practitioner Bonita Bennett, and heritage practitioner Calvyn Gilfellan. These conversations occur at a particular moment in South African life and being: in the aftermath of the Zuma presidency, in the aftermath of #RhodesMustFall, in the context of the perceived failure of the project of non-racialism, in the context of growing frustration over the intractability of historical inequality and the slow pace of change, and amid a heated national debate around the ANC government’s draft land expropriation bill. A common set of themes and preoccupations emerge: questions around race and religion; history, representation, and restitution; memory and forgetting; social justice and the abiding presence of historical injustice. Thinking inside and outside of the disciplines of art, architecture, and museum and heritage practice, these conversations present an accumulated body of wisdom and insight that might also be read as a transcript on the contemporary state of the city.