After 1987, in pool halls and city parks, high school football games, storefront churches, youth centers, and other sites where police presence was minimal, high-ranking leaders from Chicago’s largest AfricanAmerican street gang ‘‘Nations’’ began meeting to discuss the latest period of change in their respective associations. Adorned in jewelry and expensive designer clothes, and transported in luxury cars, the leaders left little doubt that underground commerce was at the heart of the gang’s activities. In between discussions of collective exigencies, most of which centered around management of their crack-cocaine trade, members ‘‘signi¢ed’’ with stories of failed or successful money laundering, new opportunities for investment, or a recent commodity purchase. Crack cocaine had arrived in the city and, with it, lucrative pro¢ts for a twenty- and thirty-something class of young black men living in the poorest neighborhoods. The involvement of gang members in the burgeoning underground trade was by no means ubiquitous: not all of Chicago’s neighborhood gangs were entrepreneurial, nor did all members of the successfully commercial groups earn revenue that could support conspicuous consumption ^ in fact, the majority earned slightly above minimum wage. 1 However, such activity was without precedent: organized entrepreneurship was an atypical venture for many of these thirty-year old gang families.