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Youth involved in the justice system remain an underserved population at elevated risk for multiple problems, including substance abuse, mental health, and sexually transmitted infections.  Many of these youth have experienced painful childhoods involving multiple forms of victimization, including abuse and exposure to trauma.  Among the causes of the problems of these youth, family issues remain significant factors needing increased elucidation.  Using data on male and female youth entering the justice system, we studied the relationships among: (1) family member alcohol abuse, family member other drug abuse, and biological parent spending time in jail or prison, and (2) youth involvement in bullying, experience of depression, being sexually assaulted, and alcohol/other drug involvement in the past year.  Results indicated family problems of alcohol use, drug use, and parental incarceration were positively correlated across both genders; and youth problems of drug use, depression, bullying, and sexual assault were also generally positively associated with one another across gender.  Gender differences were found in the prevalence of each of these problem areas, with female youth reporting higher rates of family alcohol and other drug abuse problems, parental incarceration, involvement in bullying, being sexually assaulted, and depression, than male youth. There were significant relationships between a number of family problems and youth problems, with gender differences in a number of these relationships.  For example, among boys, no family problem factors were related to being sexually assaulted, whereas among girls a significant, positive relationship was found between family alcohol problems and being sexually assaulted.  Practice implications of the findings are discussed.