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This paper explores the therapeutic work of Ana Barroso with Liam, a boy enduring acute psychological fragmentation following a traumatic accident that was compounded by intergenerational projections of unresolved grief and loss. Liam’s internalization of the analyst’s containing presence facilitated the reconstruction of a cohesive self. Parallel insights emerge from an adult patient treated by the discussant with a similar armored psyche, marked by a flat internal world and manic defenses against loss. Both cases highlight the critical role of creativity and imaginative and containing therapeutic interventions in reintegrating fragmented psyches and fostering the capacity for connection and symbolization.