This study examines the work of cooperating teachers (CTs) within a literacy leadership course to construct transgressive mentoring practices that work against the grain of what is typical in schools. Previous research on coaching preservice teachers has not focused on the work that inservice teachers do to provide mentoring towards transgressive teaching practices. We ask, how do CTs within literacy leadership courses construct transgressive mentoring practices? Through our qualitative analysis of primarily conversations about coaching, we document how seven CTs' reflections, individual and in community, led them to "inspection," "reciprocity" and "hope" in their practices as teachers and coaches. This study has implications for the teacher educators including the development of professional learning opportunities for CTs and for researchers who intend to study such learning communities across contexts.