Closely examining the relationship between the political and the utopian in five major plays from different phases of Shakespeare’s career, Hugh Grady shows the dialectical link between the earlier political dramas and the late plays or tragicomedies. Reading Julius Caesar and Macbeth from the tragic period alongside The Winter’s Tale and Tempest from the utopian end of Shakespeare’s career, with Antony and Cleopatra acting as a transition, Grady reveals how, in the late plays, Shakespeare introduces a transformative element of hope while never losing a sharp awareness of suffering and death. The plays presciently confront dilemmas of an emerging modernity, diagnosing and indicting instrumental politics and capitalism as largely disastrous developments leading to an empty world devoid of meaning and community. Grady persuasively argues that the utopian vision is a specific dialectical response to these fears and a necessity in worlds of injustice, madness and death.