The current proliferation of authoritarianism across both core and periphery is one political articulation of the current crisis of the capitalist world-system. Authoritarianism similarly proliferated in previous periods of crisis, in the 1970s and 1980s in the peripheries, and in the 1930s and 1940s in the core. In Part I of this essay, I detail how world-systems analysts have long been attuned to describing and analyzing chaotic moments in between systemic cycles of hegemony, but less attention has been given to the rise of authoritarianism in these chaotic phases. The multiple crises of hegemonic transition engenders an ideological contestation between Fascism and Communism revealing the limitations of Liberalism, the foundational ideology of the world-system. In such periods of hegemonic breakdown, anarchists developed autonomous strategies of resisting authoritarian rule at both the point of production (the worker-occupied and self-managed workplace) and at the point of leisure (the autonomous zone of the infoshop or café as resources and interventions in the joint struggle against capitalism and authoritarianism. These theories are important to recover for the contemporary fight against a resurgent authoritarianism across the world-system in the current conjuncture.