Chapter 2 considers the microregion of the Leeward Islands in terms of political economy and commercial practices. Since cross-imperial trade played such a crucial role in the formation and development of the region’s intercolonial networks, an understanding of the extent and texture of this trade, as well as the related dynamics of smuggling and investment, is key to fully grasping the other aspects of the microregion. Not only did commercial practices drive contact and competition between colonies and groups, but the flow of trade was also a crucial concern for the various regulatory attempts of individual empires in the region, in terms of both inter-imperial interaction and intra-imperial legislation. The analysis presented here forms part of the foundation for the following chapters, by examining the networks and structures of the inter-imperial microregion and some of the ways in which European metropoles responded to local conditions. The chapter also illuminates some of the shifts taking place within the region as a consequence of the emerging globalization of the early nineteenth century, a process that the Leeward Islands were initially at the center of in the Atlantic context but that ultimately led to their near-disappearance from the global economic stage.