Youth involved in the criminal justice system exhibit elevated rates of sexual risk behavior (SRB), placing them at high risk for sexually transmitted infections (STIs) and other deleterious outcomes. High levels of youth-maternal connectedness have been shown to act as a protective factor for SRB in nationally representative studies and in studies with primarily White youth samples. However, there are mixed findings in the research literature on the association of maternal connectedness and SRB among African American and Latino youth, a population who are disproportionately over-represented in the criminal justice system. Additionally, no studies to date have examined the role of maternal connectedness in SRB among justice-involved youth. This dissertation used archived data to determine if maternal connectedness can buffer against the negative effects of adverse childhood experiences (ACEs) on SRB among justice-involved youth. A secondary aim was to explore the prevalence of ACEs among youth in the sample, including several new ACE items that focus on adversity occurring outside the home. Participants (N=263) were sentenced or detained adolescent males at a large correctional facility in New York City, aged 16-18 and predominantly African American and Latino. Data were collected from the baseline interview of an intervention study conducted from 2009-2010. Youth participated in an individually administered, computer-based survey covering a range of topics, such as sexual health history, family relationships, substance use, and exposure to adverse events. Consistent with the literature, our sample of detained youth reported a high degree of SRB and a significant number of adverse experiences. Logistic regression analysis found that total ACE scores do not predict risky sexual behavior, even when controlling for maternal connectedness, substance use, age, and number of days incarcerated/detained. However, every participant endorsed exposure to at least 2 ACEs and 92% endorsed exposure to 4 or more, suggesting that the restriction in range may have obfuscated a relationship between total ACE scores and sexual risk-taking. The new ACE items, including poverty, racial discrimination, and neighborhood violence were prevalent. Additionally, several of the individual ACE items, including physical abuse, emotional abuse, and racial discrimination were independently associated with sexual risk outcomes. Maternal connectedness was negatively correlated with one type of risky sexual behavior—frequency of substance use during sex. Maternal connectedness and total ACE scores were, as predicted, negatively correlated. These findings suggest that our sample of incarcerated youth have experienced such a profound degree of adversity and trauma that perhaps ACE scores alone cannot adequately predict their engagement in risky sex. The fact that so many of the adolescents in the study endorsed the new ACE items also provides strong support for dissemination of the revised ACE inventory. This study highlights the need for greater research on risk and protective factors influencing adolescent SRB, as well as psychosocial correlates of ACEs among at-risk youth. Furthermore, given the syndemic nature of SRB and high prevalence of STIs, HIV, and ACEs in urban communities of color, future research should consider a more comprehensive and integrative approach to preventing both childhood adversity and unwanted sexual risk outcomes. Directions for future research and clinical implications are discussed.