Any fundamental examination of managerial practices must consider a philosophical conundrum at the heart of market exchange. Economically, the opportunity for profit seems to demand somebody else’s loss, and ethically, we must not take advantage of others’ misfortune. In a market system involving a multiplicity of stakeholders, profit opportunities may arise in which relationships between winners and losers are distant, indirect, or even nonexistent; their motives are multivalent; and their market participation may be intentional or accidental. Reflecting two decades later (...) upon several cases arising from the 9/11/2001 terrorist attacks, this paper describes several examples of profiting from loss that demonstrate the ubiquity and variety of the problem. It also invokes numerous bodies of literature that demonstrate the inherent complexity and interdisciplinarity of the problem and the absence of determinative principles to answer the question of when it is justifiable to profit from loss. The paper positions casuistry, the ancient philosophical art of case analysis that resembles modern business pedagogy, as a complement to ethical theory. The Loss Agency-Division of Benefits framework developed in the paper demonstrates the value of philosophy to managerial practices when economic theory is insufficient for ethically classifying and evaluating forms of profiting from loss. (shrink)