Non-Hispanic Black/African American men who have sex with men (AAMSM) have been disproportionately affected by criminal justice (CJ) involvement and HIV. One potential pathway between CJ involvement and high HIV prevalence and incidence among AAMSM is through risky sexual behavior. The goal of this study was to explore the association between recent CJ involvement, i.e., having been arrested and/or in prison/jail in the past 6 months, and transactional sex in a sample of AAMSM in Baltimore. We analyzed the baseline data of 396 AAMSM from a pilot behavioral HIV intervention conducted in Baltimore, MD, between October 2012 and November 2015. A multivariate logistic regression model was conducted to explore the association between recent CJ involvement and transactional sex. A total of 65 (16%) participants reported recent CJ involvement, and 116 (29%) reported transactional sex in the past 90 days. After adjusting for age, education, employment, sexual identity, HIV status, and drug use, recent CJ involvement was significantly associated with transactional sex (AOR 3.31; 95% CI 1.72; 5.70). Being 24-40 years (AOR 2.73; 95% CI 1.17, 6.33) or over 40 years older (AOR 3.80; 95% CI 1.61, 8.98) vs. younger and using drugs (AOR 4.47; 95% CI 2.43, 8.23) also remained independently associated with recent transactional sex. Findings of the current study contribute to the literature on the association between recent history of CJ involvement and transactional sex among AAMSM. More evidence-based HIV prevention interventions for people involved in the CJ system who are at high risk for contracting HIV, particularly racial and sexual minorities such as AAMSM, are urgently needed.