Today, Jack Hodgson is best-known as a tenacious anti-apartheid militant and for his role in Umkhonto we Sizwe (MK), the armed wing of the African National Congress. Details about his earlier life as a miner on the Rand and the Copperbelt are virtually unknown, and this helps explain why it has been assumed in the literature that Hodgson’s opposition to racial discrimination was consistent throughout his life. In fact, Hodgson was a shop steward in a whites-only trade union on the Copperbelt and a staunch proponent of the colour bar. This chapter explores Hodgson’s life and political transition to stress the role of subjectivity and argue that the impact of material conditions and experiences is not homogeneous. Many biographies of individuals involved in African nationalist movements depict a straightforward trajectory of radicalisation in response to experiences of injustice and oppression. Although Hodgson was radicalised by his experiences of industrial unrest and war, the many thousands of others who participated in these events alongside were not, or not in the same way. His biography is an illustration of how people’s lives are not an ordered sequence of actions and events, but often contradictory and fractured.