This study examined the associations of sexual risk behaviors, substance use, mental health, and trauma with varying levels of gang involvement in a sample of Los Angeles based homeless youths. Data were collected from 505 homeless youths who self reported various health information and whether they have ever identified as or been closely affiliated with a gang member. Multivariable logistic regression assessed associations of lifetime gang involvement with risk taking behaviors and negative health outcomes. Results revealed seventeen percent of youths have ever identified as a gang member and 46% as gang affiliated. Both gang members and affiliates were at greater risk of many negative behaviors than non-gang involved youths. Gang members and affiliates were more likely to report recent methamphetamine use, cocaine use, chronic marijuana use, having sex while intoxicated, and symptoms of depression, symptoms of post traumatic stress disorder. They were also more likely to have experienced childhood sexual abuse and witnessing family violence. Gang members were more likely to ever attempt suicide, experience recent partner violence, and report physical abuse during childhood. Results suggest that lifetime gang involvement is related to a trajectory of negative outcomes and amplified risk for youths experiencing homelessness. Additionally, being closely connected to a gang member appears to have just as much as an impact on risk as personally identifying as a gang member. Given the lack of knowledge regarding the intersection between youth homelessness and gang involvement, future research is needed to inform policies and programs that can address the specific needs of this population.