African-American youth are disproportionately affected by parental incarceration and the consequences of parental substance use. Many adapt to the loss of their parents to prison or drug addiction by engaging in sex-risk behavior, particularly the sex trade. These youth may engage in this risky behavior for a number of reasons. Although previous research has examined this issue, most of these studies have focused on runaway or street youth or youth in international settings. Empirical evidence on correlates of trading sex for money among urban African-American youth is practically missing. Using a sample of 192 African-American youth living in urban public housing, this paper attempts to rectify this gap in knowledge by assessing how individual and parental factors are related to the likelihood of a youth trading sex for money. The sample for this study reported a mean age of 19; 28 % reported having traded sex for money; 30 % had a father currently in prison; and 7 % reported having a mother currently in prison. Maternal incarceration and paternal substance use were associated with a higher likelihood of trading sex for money. Given the potential health risks associated with trading sex for money, understanding correlates of this behavior has important implications for the health of this vulnerable population of youth and urban health in general.