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This paper examines the use of litigation by merchants of Jewish origin plying the sugar trade route – Brazil, Portugal and the Netherlands – in the late sixteenth and early seventeenth century. It argues that the legal system was not only feasible but actually used to solve commercial disputes among traders of various origins across wide distance and different political units, even during wartime. Litigation was also frequent within the Western Sephardic and converso tradesmen, which allegedly constituted a closely-knit trading diaspora. In fact, legal coercion coevolved and interplayed with the informal mechanism for securing compliance with mercantile norms and agreements rather than competed with them for prevalence. When the informal mechanisms failed, merchants turned to the more costly, slower and doubtful legal verification and enforcement. This paper is based on notarial records from Amsterdam and Oporto, and inquisitorial files from Portugal.