Research on moral economy and medicine has focused on the Global North, disregarding colonialisms’ impact on contradictions between medical values and medical markets. Using historical sources and interviews with Puerto Rican physicians, this study examines the conflict between medical ideals and economic realities in the periphery, exploring morals, markets, and medicine in Puerto Rico. Early medical development in Puerto Rico under the Spanish and United States colonial regimes culminated in a contradictory set of medical values: government responsibility for providing healthcare, biomedical superiority, medical work as a patriotic duty, and medical legitimacy as reliant on American medicine. Puerto Rico’s attempts to institutionally balance the right to universal healthcare with use of expensive biomedical technology within the political and economic subjugation accompanying its relationship to the United States has culminated in a private, for-profit, HMO-style healthcare system (Reforma) and a healthcare crisis characterized by lack of resources and medical inaccessibility. Puerto Rican physicians’ professional identities help them make sense of moral economy contradictions, emphasizing their connection to American medicine while claiming superiority to mainland doctors for their ability to “do more with less” to ensure patients’ access to biomedical services. Doctors use their professional identities to inform and interpret socially-embedded, redistributive, cross-Caribbean community responses to the island’s healthcare crisis. This research illustrates how medical moral economy functions within a colonial environment, how neoliberalism and biomedicine are pushed onto Southern contexts better served by a sociomedical approach to care, and how neoliberal healthcare systems are supported by informal community networks.