The present study used Model-Based Cluster analysis to identify primary and secondary psychopathy variants in a mixed-gender sample of 150 adjudicated adolescents (60 % male; M = 15.2 years old). Distinct primary and secondary psychopathy groups emerged and were entered into a structural equation path model for the purpose of predicting group differences in emotional experiences reported between youth assigned to each variant. Youth characterized by secondary psychopathy reported experiencing significantly more frequent and more intense negative affect than their primary psychopathy counterparts. Frequency and intensity of affect also mediated the association between psychopathy variants and symptoms of depression, in which the secondary psychopathy group endorsed significantly more symptoms of major depression than the primary psychopathy group. Overall, these results suggest that different causal processes and affective experiences may underlie distinct trajectories to primary and secondary psychopathy variants in adjudicated adolescents. As such, youths comprising the secondary subtype of psychopathy may be more aptly considered “callous and emotional,” compared with the primary subtype who present as prototypically callous and unemotional.