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The study of adolescent psychopathy has grown from being a fringe element in psychology to a mainstream topic for research. One issue that divides scholars centers on the relationship between conduct problems and attention-deficit hyperactivity disorder (ADHD) and their relationship to adolescent psychopathy. Some state the former factor has the most crucial relationship while other scholars categorically disagree, claiming that ADHD is the strongest. The majority of adolescents assessed for adolescent psychopathy are residents at state training schools; however, many of the behaviors associated with psychopathy are seen in students assigned to their district’s alternative educational setting. In order to gauge which factor had strongest relationship with psychopathy, 80 male students, ranging in age from 12 to 18 years old, placed at interim alternative educational settings for misbehavior were assessed using the Antisocial Process Screening Device---Youth Edition (APSD-Y) to determine level of psychopathy. In addition, ADHD was assessed using both the Behavior Assessment Scale for Children- Second Edition (BASC-2) and Conners-Wells’ Adolescent Self-Report Scale-L (CASS:L); likewise, both instruments were used assess conduct problems. Each assessment instrument used a self-report method. Results indicated that of the two factors, conduct problems had a statistically significant relationship with adolescent psychopathy, while the relationship between ADHD’s and psychopathy was nonsignificant. The implications are straight forward. Adolescents with impulsivity problems are regularly sent to interim alternative educational settings for misbehaving; however, the findings of this study indicate that impulsivity alone should not be the focus when considering pathways to psychopathy. Rather, conduct problems should be considered a contributing factor as it shares a significant relationship with psychopathy. A secondary analysis using an Independent T-test was used to explore the differences between the Low and High scoring APSD-Y groups. Clinical significance was found between the two APSD-Y groups with the BASC-2 Externalizing and the CASS:L Externalizing subscales, as well as the BASC-2 Conduct Problems and the CASS-Conduct Problem scores.