Scholars of agrarian change have long debated the nature of capitalist transition in the countryside, including whether the deepened interlinking of local, national, and transnational economic activities make past trajectories of agrarian transformation unlikely to reoccur in the present. This essay makes the case that Giovanni Arrighi's work has much to add to our understanding of the agrarian question in global historical perspective. We focus in particular on Arrighi's research on trajectories of change in the Calabrian region of southern Italy, and his essay “Capitalist Development in Hostile Environments.” In this piece, Arrighi and co-author Fortunata Piselli develop two key insights. The first is that the pathways to capitalism are diverse, non-linear, and historically contingent such that within one country—or, in the case of Italy, a single subnational region—multiple trajectories can be found. The second is that the outcomes of capitalist transition vary based on a country's position in the international hierarchy of wealth, meaning that agrarian transformation is compatible with both economic development and underdevelopment. We describe the three methodological principles that enabled Arrighi to develop his analysis of capitalist transition and explain how the papers collected in this special issue reflect and extend the Arrighian approach to agrarian political economy.