Neoliberal restructuring of education is a global phenomenon that has been actively resisted by a number of K-12 teachers’ unions acting at the state and global level. These efforts have been well documented by union activists within each organization, but the accounts have been descriptive rather than analytic in nature and have masked internal, micro-political struggles for democracy, social justice, and equity faced by teacher unionists struggling to democratize their own federations. This paper uses a micro- political perspective to analyze the career histories of 25 activists affiliated with a Canadian provincial teachers’ federation that self identifies as a social justice union. By analyzing moments of conflict and collaboration between groups of activists who compete for resources but are not necessarily at cross purposes, this paper contributes to the efforts of those hoping to increase the durability of social justice teacher union activism at a local, organizational, and global level.