Adolescent suicide has been described as a major public health problem calling for the aid of researchers willing to better identify factors related to suicide risk. Suicide is the third-leading cause of death for 15 to 24 year olds. Despite the fact incarcerated adolescents act in self-destructive ways, minimal research has focused on suicide behavior among incarcerated adolescents. Existing data indicates that suicide among adolescent males is especially prevalent in the juvenile justice system. Several variables have been identified as risk factors for suicidal behavior, including interpersonal relationship dysfunction, substance abuse, and psychological variables such as depression and dichotomous thinking. Incarcerated males have been shown to be more prone to these risks than the general population. There is a need to highlight these risks in context of this population, identifying behavior patterns over the life span. Addressing the need to identify behavior patterns within the incarcerated male youth population, this study focuses on one adolescent male involved with Utah's juvenile justice system who subsequently completed suicide. The identified youth suffered from substance abuse; its effects were devastating to himself and those around him. Furthermore, his hypersensitivity to disappointing others permeated his lifelong traits and behavior patterns. Interviewees reported that such hypersensitivity began early in life, prominently influencing his subsequent self-inflicted guilt in adolescence when drug use, the decision to drop-out of school, and incarceration became traumatic. As this case study exemplified, counselors, teachers, school psychologists, family, and friends need to be aware of the increased potential for suicide in incarcerated adolescents, particularly those who struggle with substance abuse and a comorbid disorder.