While researchers have found that African American youth experience higher levels of juvenile justice involvement at every system level (arrest, sentencing, and incarceration) relative to their other ethnic counterparts, few studies have explored how juvenile justice involvement and number of contacts might be correlated with this broad range of problems. A convenience sample of 638 African American adolescents living in predominantly low-income, urban communities participated in a survey related to juvenile justice involvement. Major findings using logistic regression models indicated that adolescents who reported juvenile justice system involvement versus no involvement were 2.3 times as likely to report mental health problems, substance abuse, and delinquent or youth offending behaviors. Additional findings documented that the higher the number of juvenile justice system contacts, the higher the rates of delinquent behaviors, alcohol and marijuana use, sex while high on drugs, and commercial sex. These findings suggest that identifying and targeting youth who have multiple juvenile justice system contacts, especially those in low-resourced communities for early intervention services, may be beneficial. Future research should examine whether peer network norms might mediate the relationships between juvenile justice involvement and youth problem behaviors.