In this article, we propose a new vision of educational development that reimagines how graduate instructors are socialized and professionalized in academic settings. We describe a transgressive learning community that empowers graduate instructors with tools to reveal, mitigate, and disrupt oppressive structures in higher education. Our learning community is founded on critical race and feminist conceptualizations of pedagogical inquiry in its design, implementation, and assessment to serve underprivileged, underserved, and historically underrepresented graduate students. We argue that the intersections of marginalized and graduate student identities create distinct experiences of discrimination, marginalization, tokenism, isolation, and impostor syndrome due to a lack of sustained teaching mentorship within the academy. The transgressive learning community model that we propose in this article functions to create spaces of transgressive and transformational pedagogical engagement for graduate students who exist at the intersections of these identities.