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Abstract The expanding sugar trade linking Portugal, Brazil, and the Netherlands in the sixteenth and seventeenth centuries required enforcement mechanisms to guarantee that overseas agents would act honestly and diligently. While the recent literature emphasizes that multiple mechanisms were substitutes in addressing this problem, this article highlights that merchants chose different mechanisms to govern distinct types of transactions and explains why. A reputational mechanism relying on social and economic constraints within an ethnic diaspora governed more complex and higher-value arrangements. A different mechanism linking economic incentives to professional reputations across the diasporas plying this trade route predominated in simpler and smaller transactions. Finally, long-distance and transnational judicial enforcement supplemented these two reputational mechanisms. Capable of matching the value and complexity of transactions with the attributes of governing mechanisms, merchants were able to diversify their transactions, expand the market for agents, better allocate agents to tasks, and stimulate competition among them. The resulting decrease in agency costs was critical in such a significantly competitive market as the sugar trade. Evolving institutional choice thus reinforced the expansion of trade. These hypotheses are corroborated by data from a prosopography of merchants of Jewish origin, derived from notarial records from Oporto and Amsterdam, and from Inquisition files.