Background: This article considers the speculative and pedagogical character of campus abolitionist organizing. Extending education research into the knowledge (re)producing functions of radical activism, we draw upon the Black Radical Tradition to theorize the intersections of learning and imagination in both activism and education. Method: The article centers an autoethnographic case study emerging from the authors' experiences at University of Pennsylvania and their conflicted positions as campus organizers and educational laborers. Centering a direct action around university reparations, the paper draws on recollections of the event and its preparations as well as audiovisual and written documentation. Findings: Analyzing our experiences as educational laborers and organizers struggling toward liberation, we document movement-driven learning practices and strategies for navigating contradictions between the university's professed public mission and the realities of its exploitation of neighboring communities, which has been the focus of national campus organizing in the wake of the 2020 protests for racial justice. Contribution: We offer the concept of organizing pedagogies to foreground the role of activism in producing and disseminating knowledge and fostering contexts for collective learning, as well as the role of the radical imagination in shaping activist educators' mobilizations to advance freedom struggles within and beyond campus.