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This contribution reflects on my personal experience of publishing a biography of a controversial apartheid figure. The experience demonstrated that there are three layers of context that influence the writing and interpretation of biography: attempts to understand the context in which the historical figure lived and operated; attempts to reflect on the context in which the biographer writes; and the context in which the resulting biography is received and interpreted. I focus on the third layer, in particular the interpretative context created by the #RhodesMustFall movement. This movement, which initially converged around the statue of arch-imperialist Cecil John Rhodes, elevated the importance of historical figures in public discourse. However, it was clearly not a question of understanding the complexity of any given historical figure, which is the purview of the biographer, but rather about what the historical figure represents. Historical figures are, in effect, human symbols. The contribution then reflects on instances that demonstrate the tension between the biographer’s attempts to understand a complex historical figure and that individual’s symbolism. The most notable example of this tension was the outrage when the apartheid-era killer, Eugene de Kock, arrived in person when a biography of him was being celebrated.