This study examined the personality characteristics of juvenile probation officers and drew implications of its findings for the relationship between officers and their delinquent clientele. Twenty-six male probation officers and seven female probation officers were administered the MMPI and the La Forge and Suczek Interpersonal Check List, two components of the Leary Interpersonal Diagnostic System. Probation officers appeared rigidly conventional, controlling and hyperresponsible while idealizing behavior which is oppositional, and unconventional. This supported the hypothesis that probation officers may unwittingly reinforce delinquent behaviors in relationships with delinquent adolescents to achieve various expression of their unconventional feelings and behaviors. Methods for helping officers gain insight into this process were suggested.