While C. G. Jung largely eschewed the term “narcissism” following his split with Freud, his writings describe in archetypal language conditions that closely resemble narcissistic disorders. One such archetype, the puer œternus, appears phenomenologically similar to clinical descriptions of Heinz Kohut, in particular his case of “Mr. Z”, and what has been termed elsewhere as hyper-vigilant (as opposed to oblivious) narcissism. While narcissism as a concept has been addressed at length in post-Jungian literature, this paper uses Kohut's case as a starting point to explore the corresponding alchemical process of life-renewal, the ambivalence of regression, and the dangers of the lesser coniunctio, or the archetypal basis of the weak ego's desire for incest with the collective unconscious in the form of the Great/Terrible Mother. It also addresses the clinical relevance of this topic when working with the individual who fits Kohut's description of Tragic Man, or Jung's puer œternus.