This study explores the shifting roles of teacher unions in pre-and post-independence Namibia, against the backdrop of a changing political context. My aim was to understand the roles of teacher unions both before and after independence in Namibia, and to explain how they changed in the different political contexts. To do so, I examined the teacher union roles in three distinct phases, namely pre-independence, immediately post-independence, taking in the period from 1990 to 1999, and the last decade, from 2000 up until today. In approaching the research questions, I worked on the assumption that understanding and explaining the roles of teacher unions in pre- and post-independence Namibia could best be achieved by interacting with participants who were or had been involved in education and the teacher unions in Namibia. I argued that their experiences would be important in constructing knowledge on the unions, particularly regarding their roles before and after independence. I chose a narrative design for the study, because it allowed me to interact with the participants to gain deeper meanings from their individual perspectives. Narrative design was appropriate to this research, because it also allowed me to trace the way events in education mirrored those in the national political arena, and to explain why particular tendencies emerged. I used the information collected during the interviews and document analysis as the data for the study. Four themes emerged regarding the roles of teacher unions in the contexts of pre- and post-independence Namibia, around which I conceptualized the study. These were the shifting historic roles of these unions in Namibia, the institutional frameworks and modalities for union participation, the contextual factors relating to the roles of the unions, and the changed roles of the unions in contemporary Namibia. The findings of the study suggested, firstly, that teacher unions play different roles in different political contexts, and that these roles are shaped by contextual factors. Secondly, the research established that the unions in the post-independence contexts did not necessarily have a vision of a labour-driven process of radical strategic change, as postulated by the theory of strategic unionism. Instead, the findings suggest that teacher unions in contemporary Namibia are influenced and shaped by the broader political and social factors of a new hierarchical political culture, by political and economic middle-class aspirations, and by undefined party-government-teacher union relationships. I conclude the study by suggesting an expansion of the concept of strategic unionism to include the nuances of political and economic contexts and aspirations.