Psychopathy is typically considered to include a myriad of personality traits. We explored how psychopathic features, assessed using the Psychopathy Checklist: Youth Version (PCL: YV; Forth, Kosson, & Hare, 2003), are interrelated in a network model among 1170 serious offending boys. Results showed callous/lack of empathy and irresponsibility are among the most frequently co-occurring features. Callous/lack of empathy, manipulation for gain, and serious criminal behavior were the most influential items among delinquent boys with elevated psychopathic tendencies. This study extends the understanding of psychopathic traits as an interconnecting network of features into offending adolescent boys, suggesting that certain interactions between certain features in youth may facilitate the manifestation of psychopathy into a stable personality trait in adulthood and also highlights the possibility that more common and less common symptom constellations make up psychopathy in delinquent youth. However, it should be noted that the level of psychopathic traits matter as to which features are central, with grandiose manipulative traits common at high levels of psychopathy (discriminating), and callous traits common even at low thresholds. These findings suggest that network analyses should consider the level of psychopathic traits (high v. med-to-low) when discussing which features are “central” or common.