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This paper examines the history of relations between psychiatry and psychoanalysis based on questions pertaining to the psychoanalytic psychotherapy of psychotic disorders. New information was obtained through an empirical analysis of 59 case reports from everyday clinical practice and 20 case reports from a well-known research trial. Attention was paid to careful retrospective DSM-IV assessment and standardized outcome evaluation. Then, the data were computed and the results were used to contrast current beliefs on what the best treatment options are in this field. These findings suggest that studies on the many clinical and psychopathological questions raised by the psychoanalytic treatment of individuals with psychotic symptoms had been biased by poor diagnostic assessment and inadequate hypothesis testing. Careful reconsideration of these issues may improve the relationship between psychiatry and psychoanalysis, and their respective clinical approaches.