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The author considers the role of the human person’s imagination, including its creative “illusion-crafting,” in the integration of existential anxiety and grief. Such anxiety and grief are deemed revelatory of truths about human existence, in particular human being’s “thrown-relationality,” and the “embeddedness-vulnerability” that derives from it. As such, the integration or dissociation of such affectivity is central in the developmental question of whether the person ontologically as well as psychologically owns and individuates around her inherently relational existence. The author advocates for a clinically trusting attitude toward the person’s imagination. This attitude would be grounded in the presumptively generative function of subjectivity imaginatively facilitating its own integration of painful existential emotion. The author illustrates varieties of sustaining illusion—including transitional phenomena, transference “phantasy,” metapsychological entities, everyday colloquialisms, and reifying linguistic imagery—that advance the person’s integration of such painful affect into her sense of self. Integral to all such forms of illusion is an emotional process called “decontextualization.” Autobiographical material of traumatic fatherloss and maternal denial is offered to show that shattered confidence in one’s capacity to craft sustaining illusion is as central to emotional trauma as the shattered content of such illusion. Finally, after showing that people bond and group together around shared illusions, the reader is encouraged to cherish and feel pride in, rather than disdain for, the human imagination, its illusion-crafting, and the important role these creative phenomena play in the person’s integration and tolerance of existential anxiety and grief.