This book explores how a small number of male and female slaves, and some free women, at Rome in the first and second centuries ce prospered in business amidst a population of generally impoverished free inhabitants and of impecunious enslaved residents. It focuses on two anomalies to which only minimal academic attention has been previously directed: (1) the paradox of a Roman economy dependent on enslaved entrepreneurs who operated, and sometimes achieved personal affluence, within a legal system that supposedly deprived unfree persons of all legal capacity and human rights; (2) the incongruity of the importance and accomplishments of Roman businesswomen, both free and slave, successfully functioning under legal rules that in many aspects discriminated against women, but in commercial matters were in principle gender-blind and in practice generated egalitarian juridical conditions that often trumped gender-discriminatory customs. Slaves’ acquisition of wealth was actually aided by a surprising preferential orientation of the legal system: Roman law—to modern Western eyes counterintuitively—privileged servile enterprise to the detriment of free enterprise. This volume also examines the casuistry through which Roman jurists created “legal fictions,” facilitating a commercial reality utterly incompatible with the fundamental precepts that legal experts (“jurisprudents”) continued explicitly to insist upon.