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This paper was written in the context of a conference—the 2017 Annual Conference of the International Association of Psychoanalytic Self Psychology in Chicago—and a plenary panel, both dedicated to the theme, “Empathic Depths and Relational Leaps: Creating Therapeutic Possibility.” Jeffrey Stern’s paper, “The Pilgrim’s Progress: A Therapist and Patient Journey to London,” had been one of the inspirations for this choice of theme; and selecting it as the Keynote Address provided the ideal platform for launching it. Because the format of the evening Keynote Address afforded only a limited context for considering the far-reaching implications of the paper, it was decided to devote the first plenary session, the next morning, to an in-depth consideration of its ramifications for contemporary psychoanalytic practice. Because Jeffrey, an accomplished psychoanalytic scholar and author, had chosen to write his paper in the spirit of the treatment it was describing—namely in a narrative style closer to a short story than a discursive psychoanalytic paper—I felt the paper invited a theoretical analysis of what Jeffrey was implicitly doing with his patient Drum, and an attempt to put into words the extraordinary conditions that made their high-risk frame expansion plausible, and ultimately profoundly therapeutic.