This chapter presents Miguel de Unamuno’s engagement with Cervantes’ Don Quixote as a profound meditation on tragedy. For Unamuno, Don Quixote embodies the tension between illusion and reality, persistence and failure, faith and despair. His “quichottism” is not mere folly but a form of existential heroism: a refusal to accept the finality of death and meaninglessness. The chapter explores how Unamuno, in dialogue with Nietzsche, Pascal, and Kierkegaard, develops a philosophy of immortality, longing, and faith, grounded in the tragic impossibility of resolution. Don Quixote’s struggle illustrates the human condition: to live is to fight against despair, even at the cost of absurdity. Unamuno’s tragic vision embraces paradox, affirming life in its brokenness and uncertainty. Law and politics, the chapter concludes, can also learn from Quichottism: true justice requires faith beyond rational calculation, sustained by the tragic endurance of hope where certainty is unattainable.