This book grapples with what it means when education and democracy are at an end: when these two foundational aspects of our society seem to have reached a culminating point, no longer appearing to produce and make sense amid the crises of our time. Engaging topical political events and mobilizing a variety of cultural resources, Di Paolantonio shows that today the possibility of the future and the significance of an expansive transgenerational sensibility are radically in question as trends toward destruction, cruelty, and banality are steering world-defying calamities, and sparking “chronopathologies” of doom and despair among the planet’s occupants. Unfolding his argument through a series of accessible chapters that draw on contemporary philosophy, educational thinking, and cultural-artistic works, Di Paolantonio explores how the transgenerational sensibility retains a possibility we might tap for overcoming the impasses of our time.