How can we reinvigorate the human capacity for political judgement as a practical activity capable of addressing the uncertainties of our postfoundational world? The book takes up this challenge by drawing on the historically attuned perspective of 20th-century philosophies of existence - in particular the work of Jean-Paul Sartre, Simone de Beauvoir, Albert Camus and Hannah Arendt. Displacing the lingering rationalist temptations, Masa Mrovlje engages these thinkers' aesthetic sensibility to delve into the experiential reality of political judgement and revivify it as a worldly, ambiguous practice. The purpose is to illustrate the prescient political significance of existentialists' narrative imagination on two contemporary perplexities of political judgement: the problem of dirty hands and the challenge of transitional justice. This engagement reveals the distinctly resistant potential of worldly judgement in its ability to stimulate our capacities of coming to terms with and creatively confronting the tragedies of political action, rather than simply yielding to them as a necessary course of political life.