HIV burden in the United States is geographically and demographically heterogeneous. While efforts over the last few decades have reduced HIV incidence, young black men who have sex with men (YBMSM) account for a significant portion of new HIV diagnoses compared to any other race and age group. The Centers for Disease Control and Prevention has allocated funding to help reduce HIV in the YBMSM community; however, their recommended screening/treatment criteria do not emphasize demographic specificity. To better guide more applicable screening guidelines specifically for YBMSM, we examine demographic, behavioral, sexual network, and biological predictors of HIV status among YBMSM in two demographically distinct cities with high HIV burden in the United States: Chicago, IL and Los Angeles, CA. We perform multivariable logistic regressions to identify predictors of HIV in these populations. We found that having a history of syphilis was the only statistically significant predictor across both cities despite inclusion of other characteristics previously shown to be associated with HIV among YBMSM. Syphilis history could be a powerful HIV risk indicator for YBMSM and, therefore, should be integrated into clinical screening practices for critical biomedical prevention options like HIV pre-exposure prophylaxis.