Once seen as a terminal diagnosis, HIV can now be managed as a chronic disease for those with access to care and life-saving pharmaceuticals. However, while antiretroviral drugs (ARV) have contributed to a reduction in HIV-related deaths, progress in the fight to eradicate HIV – particularly in underserved communities – has stalled (CDC, 2020; Millett et al., 2012). Using data from Khanna and colleagues' (2016) uConnect study – a project examining the health of Young Black Men who have Sex with Men (YBMSM) from the South Side of Chicago – this study aimed to identify the relationship between marijuana use, executive functioning, and HIV serostatus among members of this group. Specifically, analyses were run to understand how marijuana use and executive functioning interact with – and individually impact – HIV serostatus. In other words, does marijuana use impair executive functioning? Are higher levels of marijuana use associated with HIV seropositivity? Are impaired executive functions associated with HIV seropositivity? And summarily, does the potential negative impact of executive functioning mediate the relationship between marijuana use and health outcomes? Linear regressions were used to determine the relationships between marijuana use frequency and executive function composites and subdomains. Logistic regressions were used for binary outcomes, specifically marijuana’s impact on HIV serostatus and executive functions’ impact on HIV serostatus. Secondary models were created that adjusted for covariates recognized in relevant literature. Results suggest that heavy levels of marijuana use are associated with poorer executive functioning across all domains and indexes. After controlling for demographic and psychiatric variables, analyses failed to find any significant relationships between marijuana use, executive functioning, and HIV serostatus. Thus, the hypothesis that marijuana use and executive are significantly associated with HIV serostatus among YBMSM was not supported by the data. Future longitudinal research needs to be conducted to determine if broad structural barriers drive disparities in HIV care continuum outcomes.