This chapter investigates the tragic character of decision, where freedom collides with necessity and history. Drawing on Kierkegaard’s Philosophical Crumbs and his Concept of Anxiety, it argues that decisions must be made in conditions of radical uncertainty and risk, where truth cannot be secured by rational calculation. Classical tragedy illustrates how decision exposes individuals to guilt, offense, and irreducible responsibility. Philosophy, theology, and law likewise reveal that justice cannot be separated from this temporal, tragic dimension. Decisions unfold within history but are never entirely determined by it, opening a space for freedom that is simultaneously burdened by finitude. The chapter develops a phenomenology of the encounter, showing how conscience and openness define the tragic character of decision. Law, in particular, requires decisions that remain haunted by guilt and insufficiency. Far from being reducible to technique, decision is a profoundly existential act, inscribed in time and inseparable from tragedy’s unresolvable paradox.