In Eichmann in Jerusalem , Hannah Arendt struggled to defend the possibility of judgment against the obvious problems encountered in attempts to offer legally valid and morally meaningful judgments of those who had committed crimes in morally bankrupt communities. Following Norrie, this article argues that Arendt’s conclusions in Eichmann are equivocal and incoherent. Exploring her perspectival theory of judgment, the article suggests that Arendt remains trapped within certain Kantian assumptions in her philosophy of history, and as such sees the question (...) of freedom in a binary way. The article argues that Adorno’s philosophy of freedom provides the resources to diagnose and overcome Arendt’s shortcomings. Adorno’s position provides a way of embracing the antinomical character of judgment, by emphasising the need for elements of reason and nature in the phenomenon of freedom. In Adorno’s lights, judgment becomes an attempt to express a ‘spirit of solidarity’ with the tragic status of the potentially free but actually unfree subject of modernity. (shrink)