"Political criminals" of the early 20th century were adjudged to be psychopaths, a term which was generally accompanied by a negative moral judgement. However, other more positive appraisals were also made at this time. These contradictory moral judgements by psychiatrists expose the need for an examination of the historical development of concepts, traditions and moral debates associated with political criminals (anarchists, assassins, revolutionaries). This will be undertaken in the context of psychiatry/ criminology, security (and surveillance) policy as well as culture and the arts in German-speaking countries from 1880 to the early 1920s.