Homeless youth are at increased risk for involvement in the criminal justice system. This study investigated childhood trauma as a risk factor for arrest or jail among a sample of youth seeking services at drop in, shelter, and transitional housing settings, while controlling for more established risk factors including: substance use, peer deviance, and engagement in survival behaviors. Standardized and researcher developed measures collected quantitative data through face-to-face interviews with youth (N = 202). Two sequential logic regression models identified significant predictors of arrest and jail, with a particular interest in the effects of childhood maltreatment. Youth with a history of physical abuse were nearly twice as likely to be arrested and to be jailed compared to non-abused youth, controlling for the significant influence of drug use and survival behaviors. These findings suggest the need for trauma screening and trauma-informed services for homeless youth at risk of illegal behavior.