Who was 'Stanley'? What can this single case contribute to criminological theory? These questions remain inadequately answered despite two books and numerous articles devoted to The Jack-Roller. This article shows that scholars have been too willing to accept Stanley's account as 'told', over-eager to read him as a 'social type' and too slow to interrogate critically the relationship between Stanley's psychological defensiveness and his socio-cultural background. Reconsidering Stanley's account of himself from a psychoanalytically informed psychosocial perspective, this article sheds new light on Stanley's family relationships, jack-rolling and somewhat precarious desistance from crime. The central argument of this article is that it is only through exploring what Stanley said through the prism of his unconscious defences against anxiety that both the particularities and typicality of his life can be properly grasped and the case's wider theoretical significance fully realized.