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This article is a speculative reflection on psychotherapy's ubiquitous interest in the representation of foundational experience in image and narrative. In particular, it presents an inquiry into the connections between Gaston Bachelard's phenomenology of the imagination, the narrative framing of Bowlby's attachment theory and the encounter with death experienced in the context of palliative care. Four real life narratives demonstrate the power of strong imagery in holding together the intense experiences of grief, anticipatory grief, and attachment. These narratives lead the reader through each of these connecting ideas, allowing a distinction to be made between the constructed meaning suggested by narrative (often including imagery), and the impact of that image itself (often contextualised within a narrative) before it is reflected on and created as an object of meaning. The author explores both the different and complementary nature of these distinctions using the seminal work of D. W. Winnicott on transitional phenomena and play. One speculative conclusion reached is that the kind of imagery and narrative generated by people encountering death can be understood as a form of brutal play, which allows individuals to negotiate the transitional, liminal experience of grief and anticipatory grief along with the attendant attachment experience evoked therein.