Juvenile offenders are particularly at risk for HIV because of their substantially high rates of risk behaviors, high rates of substance use disorders and psychopathology. Most studies have focused on risk behaviors among incarcerated youth. This study sought to determine if an arrest history could serve as a marker for HIV risk and substance abuse among a community-based sample of high-risk adolescents and young adults. Adolescents (N=1400; mean age=18 years) who participated in a larger multi-site HIV prevention program in three states (GA, FL and RI) provided baseline data on sexual risk, substance use, attitudes and mental health history. Participants were grouped as arrestees (N=404) and non-arrestees (N=996) based on self-reported arrest history. Juvenile arrestees reported more alcohol and drug use, substance use during sex, unprotected sex acts, STI diagnoses, suicide attempts and psychiatric hospitalizations than non-arrestees. Having an arrest history may serve as a marker for adolescent HIV risk and substance abuse. Effectively screening adolescents for legal history and responding to the psychosocial and health needs of these high-risk adolescents could increase necessary engagement in substance use and mental health treatment, reduce HIV risk in the community, and reduce costs to the legal, medical and mental health systems.