This session will examine various ways in which medieval Iberians negotiated problems around ideas of legitimacy and sovereignty. The intercultural, interfaith rhythms of the Mediterranean world created multiple, overlapping systems of authority. Opportunities existed for cooperation, but also competition, as these papers will demonstrate the ways in which individuals created a political vocabulary with which to assert themselves and delegitimize others. The multiplicity of options for authority also fostered the opportunity to bounce between different types of jurisdictions, in order to seek the one that was most profitable for an individual or corporate entity. These papers will demonstrate the resulting tension between top-down approaches to the imposition of sovereignty and the bottom-up creation of means to resist and/or limit unchecked authority. However, resistance was not the only desired outcome of medieval Iberians. These papers will assert the possibilities of working within the system, as they examine the motives of exploitation and self-profit, leveraging the rhetoric and ideas of different groups for socio-economic, political, and personal gain. Finally, these papers will assert the role of historians in contextualizing conceptions of sovereignty and populism. These historiographically problematic concepts — including those buzzwords specific to Iberian contexts: Reconquista and Convivencia — remain at the forefront of popular imaginations of the Middle Ages. Taken collectively, these papers will challenge these modern myths through providing medieval perspectives on recurring crises of political sovereignty and legitimacy. This session responds to the MAA’s theme for co-sponsored sessions: Medieval Perspectives on Modern Crises.