This study looks at the experiences of pre-service teachers who began their student teaching assignments amidst the 2012 Chicago Teachers Union strike. Four yearlong student teachers reflected on their understandings of teaching, unionism, and activism before, during, and after the strike. Findings suggest pre-service teachers need greater opportunities to a) learn about the politics of school, b) work with families and community members outside of school, and c) develop as truth-telling political activists.