Psychopathy and trauma exposure are robustly associated with youth conduct problems, but the interrelation of these constructs is unclear. The objective of the present study is to examine psychopathy mediation effects related to trauma events and trauma reactions and juvenile delinquency, conduct disorder, crime seriousness, and proactive overt aggression outcomes. The sample consisted of N =388 ( M = 16.01 years, SD = 1.03 years, age range = 13–18 years) male youths from Portugal. Path analysis procedures revealed that psychopathy partially mediates the relation between trauma events and the juvenile delinquency, conduct disorder, crime seriousness outcomes, and fully mediates the relation between trauma events and the proactive overt aggression outcome. Trauma reactions have no direct significant effect on psychopathy, and psychopathy does not mediate the relation between trauma reactions and the examined outcomes. Research on trauma and adverse childhood experiences should encompass both events and reactions to those events as they have differential associations with psychopathy and externalizing outcomes. Trauma-informed service, supervision, and treatment is essential for understanding antisocial development and psychological maladjustment among youth.