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The Dark Triad is represented by three inter-related personality characteristics thought to share a “dark core” – that is, to be associated with a range of negative outcomes. Few studies, however, have examined the association between the Dark Triad and delinquency. We investigate this link along with its connection to another potent predictor of crime, low self-control. Self-reports were collected from 1,000 high school youth in a large Saudi Arabian city. Assessments included the “Dirty Dozen” to measure the Dark Triad, an adapted Grasmick scale capturing self-control, and a traditional measure of delinquent involvement. The Dark Triad was strongly predictive of delinquency, especially violent delinquency where it accounted for the effects of self-control. Yet it exerted no significant effect on drug-based delinquency. However, an interaction between the Dark Triad and low self-control remained substantive and predictive across all models, where low self-control amplified the effects of the Dark Triad on delinquency. These findings suggest that the two scales likely tap into a broader personality construct, namely psychopathy. We call for a greater realization of the malevolent personality characteristics of certain offenders and their behavior which is likely to be more violent, callous, and predatory in nature.