Detained minors display substantial mental health needs. This study focused on two features (psychopathology and self-esteem) that have received considerable attention in the literature and clinical work, but have rarely been studied simultaneously in detained youths. The aims of this study were to examine gender differences in psychiatric disorders and clusters of self-esteem, and to test the hypothesis that the cluster of adolescents with lower (versus higher) levels of self-esteem have higher rates of psychiatric disorders. The prevalence of psychiatric disorders was assessed in 440 Belgian, detained adolescents using the Diagnostic Interview Schedule for Children-IV. Self-esteem was assessed using the Self-perception Profile for Adolescents. Model-based cluster analyses were performed to identify youths with lower and/or higher levels of self-esteem across several domains. Girls have higher rates for most psychiatric disorders and lower levels of self-esteem than boys. A higher number of clusters was identified in boys (four) than girls (three). Generally, the cluster of adolescents with lower (versus higher) levels of self-esteem had a higher prevalence of psychiatric disorders. These results suggest that the detection of low levels of self-esteem in adolescents, especially girls, might help clinicians to identify a subgroup of detained adolescents with the highest prevalence of psychopathology.