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Criminologists in the Positive tradition have long been interested in the effects of time-stable personality traits on offending. A large body of research now shows that a wide variety of traits (e.g., impulsivity, an angry disposition, callousness, and risk seeking) distinguish those who commit crimes from those who do not. Yet, very little of this work has drawn from comprehensive personality models, such as the Five-Factor Model. This is problematic because without these models, traits are studied haphazardly and with little understanding of how they come together to describe the criminal personality. Thus, the purpose of this dissertation is to advance scholarship on the personality correlates of crime by examining the relationships between the five major dimensions of personality (the Big Five) and offending. In addition to these main effects, the current study also examines mediating and moderating effects to understand how the Big Five affect offending and whether these effects are contingent on levels of criminal opportunity. To this end, data from the Pathways to Desistance Study—a longitudinal study of 1,354 youth adjudicated for serious crimes—was examined. Results from the analyses showed that (1) higher levels of Conscientiousness, Agreeableness, Emotional Stability, and Openness predicted less offending six months later, (2) these effects operated partially through moral disengagement (a measure of antisocial attitudes), and (3) the effects of Agreeableness were conditional on levels of criminal opportunity (i.e., time spent in unstructured socializing with peers and perceived neighborhood disorganization). The theoretical implications of these findings and directions for future research are discussed.