Recent developments in criminology have included a revival of interest in offenders' biographies and inner emotional experiences, and a stress on the importance of self-understanding for an understanding of crime. These approaches recall discussions of probation practice from the 1950s to the early 1970s, in which writers sought to make sense of the psychoanalytic emphasis of social work training. The article discusses the most striking of these efforts, by Clare Winnicott and William Jordan, and explores their relevance to current thinking and research on probation, in which the importance of the relationship between offender and supervising officer is once again receiving close attention.