This study sought to compare the long-term course and outcome of a group of special hospital discharges subdivided by theft legal classification into those with psychopathic disorder or with mental illness, Serial case-note reports on 75 men and 20 women with psychopathic disorder were compared with 70 men and 19 women with mental illness (93% schizophrenia) on a number of outcome measures. The mentally ill were matched to a consecutive group with psychopathic disorder and all the patients were on restriction orders. Mortality for both men and women was twice that of the population base rate adjusted for age and the length of follow-up but there was no difference between the two groups. Both sex and the legal classification affected the course of patients after their discharge. Men with psychopathic disorder were twice as likely to be convicted and four times more likely to be imprisoned compared with mentally ill men. They were also three times more likely to obtain work and four, times more likely to develop a relationship. Females generally had a more satisfactory outcome than males irrespective of the MHA classification. These results show that outcome after discharge is complex with re-offending and psychosocial adjustment being discordant. We, confirm previous findings, that offending is more common among men with psychopathic disorder after discharge, despite which the long-term course for many in this group was very good. We also identify men with mental illness as having a poor psychosocial outcome.