This article analyzes structures of feeling among the generation of trauma carriers who grew up under Pinochet’s dictatorship. Drawing on interviews with thirty-seven cultural producers (including filmmakers, novelists, visual artists, and memory activists), we shed light on the generational memory work involved in processing cultural trauma, emphasizing the emotional force behind memory transmission in postconflict societies dealing with legacies of terror. Drawing on Raymond Williams’s notion of structures of feeling, we explore how the generational memory of children during Pinochet’s dictatorship is shaped by melancholic intergenerational identification with past struggles. This intergenerational bond is characterized by melancholic affect in representing the previous generation, which is rooted in experiences of state violence and resistance and plays a key role in processing historical trauma and shaping contemporary social critique in postconflict Chile.