In this article we take the example of smuggled brazil wood to study the complex relationship between smuggling and the development ofoverseas empires. We trace the legal framework provided by the Portuguese monarchy and the WIC for the exploitation of brazilwood, from the logging in Brazil to the import into the European consumption markets. We also provide a glimpse of the many groups and the different ways in which the legal frameworks were circumvented by the cunning of private entrepreneurs looking for profit and efficiency in the business of acquiring and distributing brazil wood from production outlets into consumption markets. Furthermore, in order to understand the different gradations and added complexities of avoiding established colonial monopolies, we showcase the entrepreneurial choices that contributed to the subversion of the legal frameworks imposed by the institutions of early modern empires.