Cleckley (1941) hypothesized that true or "primary" psychopathic individuals have "good" intelligence. This study examined the relation between psychopathy and intelligence in 122 detained children and adolescents. We used the Psychopathy Checklist–Youth Version (PCL–YV; Forth, Kosson, & Hare, 2003) to assess psychopathy and administered novel intelligence measures to tap diverse interpretations of the intelligence construct (e.g., traditional and triarchic intelligence). Structural equation modeling indicated that dimensions of psychopathy and intelligence were related in unique and important ways. In particular, psychopathy traits reflecting a superficial and deceitful interpersonal style were positively related to intellectual skills in the verbal realm (Kaufman's Brief Intelligence Test [K–BIT]; Kaufman & Kaufman, 1990) and a nontraditional intellectual measure reflecting creativity, practicality, and analytic thinking as measured by Sternberg's Triarchic Abilities Test (STAT; Sternberg, 1993). Finally, the results also suggested that psychopathy traits reflecting disturbances in affective processing were inversely associated with verbal intellectual abilities. Thus, Cleckley's hypothesis was partially supported by the data, when taking into account the facets of psychopathy and when examining intelligence from the perspective of traditional and more novel and contemporary intellectual models.