This paper reads Roger Simon's concept of "transactional memory" in relationship to D. W. Winnicott's theory of "transitional space" to examine the emotional dimensions of making historical significance. Drawing on a personal memory of archival study with Simon, I suggest that his attention to the ethical qualities of remembrance at the same time offers a theory of remembrance as a work of creative play that sets into motion the painful and hopeful process of working through the anguish of loss.