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In its correspondence with Pastor Pfister about a young American man, A.B., Freud wonders about the diagnosis and is surprised that this patient seems to shift from neurosis to psychosis. This examination raises questions about Lacan’s structural approach and approach to neurosis, psychosis, and perversion. By revisiting the case in detail, we try to rebuild A.B.’s structure. First of all, it is important to put the case into perspective, in the context of Freudian theory and its evolution. Then, the diagnosis of schizophrenia can be questioned. Lastly, A.B. seems to be “Gingerbread Man,” a case mentioned by Freud in Inhibitions, Symptoms, and Anxiety (1926). This is a case of infantile phobia, which means that maternal castration was experienced. A trait of perversion, in the form of fetishistic masturbation, appears crucial in this (at least partial) recognition of castration. However, without being able to know the diagnosis with certainty (due to some missing elements), we show that Freud is rather close to a structural approach and in his attempts he tries precisely to pose a diagnosis in terms of structure.