The original inspiration of Hannah Arendt’s last work, The Life of the Mind, was the question of whether human thinking could help us resist evil. Arendt concluded that its answer was positive: thinking was a shield against evil. But, subverting this claim, her magnum opus, The Origins of Totalitarianism, showed that thinking could not have served as a moral safeguard in the history of Nazism. Conversely, Arendt’s interpretation of that same history, in her most controversial work Eichmann in Jerusalem, revealed an all too real defense against evil: human judgment. But, paradoxically, the model of judgment that she sketched in her philosophy of mind denied the survival of judgment under the historical conditions of Nazism, transforming its existence into a mysterious puzzle. This essay thus argues that Arendt’s philosophical thinking—her conceptions of thinking and of judgment—clashed with her understanding of the history of Nazism, and this conflict disorganized her views on morality in the time of this, the greatest political and historical crisis of the modern West.