Over the course of the late 1920s and into the 1930s, states tightened their borders, cracking down on migration and on transnational trade as a response to global economic turmoil and racialized discourses of immigrant inassimilability. In Mexico, popular discourse increasingly attributed economic decline to the presence of immigrants whose nationality, race, and religion marked them as undesirable. Sephardic Jewish migrants who emigrated from Ottoman and once-Ottoman states had begun to arrive in Mexico at the turn of the century, and relied on their connections with coreligionists in, and frequent travel to the eastern Mediterranean, France, and the United States for social and economic upward mobility within Mexico. Growing xenophobic discourse and restrictive economic and migratory policies in Mexico, the United States, and Turkey threatened the livelihoods, and sometimes the lives, of these migrants. This paper argues that Sephardic Jewish migrants responded to immigration and commercial restrictions along the various nodal points of their diaspora by mobilizing commercial, familial, and patronage networks that traversed the Mediterranean, Atlantic, and Caribbean. Drawing on court, immigration, secret police, and consular records, as well as press sources from Turkey, France, the United States, Cuba, and Mexico, this paper traces the development of the illicit trafficking of silk, heroin, and people, which followed preexisting Sephardi commercial and familial trajectories and which was sometimes literally embedded within licit merchandise. It thus explores how migrants circumvented legal regimes at local, national, and international levels, the fluidity with which they played divergent legal systems against each other, the persistence of deep transnational ties in spite of state attempts to legislate against precisely this type of behavior, and how such ties enabled individuals to adapt when their merchandise, and they themselves, became illegal.