Academic administrators are evaluated periodically. Thus, every decision comes with potential career consequences. This simple observation has important implications for understanding how higher education institutions are managed. This paper takes a step towards understanding how universities evaluate their academic administrators by investigating Canadian university decanal reappointments. The sample included 13 reappointed and one non-reappointed deans and the analysis focused on organizational politics. The paper proposes a framework based on formal, normative, and moral criteria to adjudicate political behaviour and finds reappointment politics to be simultaneously embedded, necessary, and problematic. The implications for research, practice, and policy are discussed.