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This paper describes the psychoanalyses of two individuals, a child (Andrew) and an adult (Quentin), who suffered from early disruptions in their families. Their fathers played prominent roles as caregivers during prolonged periods and buffered the traumatic loss of their mothers. Both Andrew and Quentin had family histories of depression and both developed depressive and characterological difficulties marked by disturbances in the regulation of aggression, with sadistic and masochistic features. Their early childhoods and experience of recurrent loss, longing, and anger were reconstructed during psychoanalysis. Psychoanalysis was therapeutically useful in relieving acute symptoms and in helping both patients move ahead in their development more securely and less burdened by diffuse, inner- and outer-directed rage. Andrew returned for psychotherapy twice, in early and late adolescence, and it was possible to follow the course of his character development during the transition from childhood into young adulthood. Using the clinical psychoanalyses as a base, the paper describes aspects of the development of character with a special emphasis on the roles of loss and the representation of aggression.