This study examined the childhood history of maltreatment, peer relations, and externalizing problems among individuals who manifested low, moderate, or high symptom levels of paranoid personality disorder (PPD) in adolescence. Participants included 174 children who attended a longitudinal summer camp research program between the ages of 9 to 12. Multiple sources of information (self-, peer, and counselor reports) were utilized. Subsequently, they participated in a personality disorder assessment during adolescence (mean age = 15.30). The results indicated that children who manifested higher levels of PPD symptoms in adolescence had higher odds of having a history of child maltreatment. Children who manifested high levels of PPD symptoms in adolescence showed a faster growth rate for peer bullying and externalizing problems in childhood. In addition, their peers rated them as less cooperative, less likely to be leaders, and more likely to initiate fights. These findings suggested that children who manifested elevated PPD symptoms in adolescence had shown early signs of behavioral disturbances in childhood, some of which gradually worsened as they approach adolescence.