The tendency in our political moment for fascists to appropriate medieval symbols and stories for their own ends was preceded by the same phenomenon in the middle of the twentieth century. Then, as now, thinkers of various kinds challenged the Nazi mischaracterization of the Middle Ages, with some thinkers going even further, finding in the medieval world potential solutions to problems that plague modernity. Hannah Arendt was one of those thinkers. Her engagement with the Middle Ages was profound, stemming from her dissertation on St Augustine, to her sustained discussion of both Augustine and John Duns Scotus in her final work, The Life of the Mind. Arendt’s appropriation of these thinkers was political in the early part of her career, in which Augustine provided her with a framework for a political community based on the shared experience of loving one’s neighbor, a vision she articulated in her dissertation, Love and Saint Augustine, but that also appeared at key moments as a potential solution to the problems discussed in The Origins of Totalitarianism. Later in her career, Arendt’s writings on medieval thinkers turned more phenomenological, as she explored those aspects of the human condition that underpinned her earlier political work. For Arendt, Augustine, and especially Duns Scotus, provided a robust understanding of free will, which is necessary for political activity and the creation of new forms of living together. Ultimately, Arendt beliefs, especially about race, make it impossible to uncritically adopt her positions in our own moment. And yet, her thoughts about the Middle Ages can still provide us important ways to think about our present crises.