We present Groddeckian psychoanalytic psychosomatics in practice through two case studies. Groddeck pioneered the application of psychoanalysis to organic diseases, but his ideas have not been explored adequately. It is necessary to reappraise his concepts to develop their potential in psychoanalysis. We aim to demonstrate the efficacy of the Groddeckian approach by presenting two cases: a case of conversion of a boy who entered a semi-comatose state due to unattended emotional experiences and a man who developed a “sick role” resisting all medical interventions. In both histories, it is possible to see how disease and subjectivity intertwine in a complex unity of mind and body.