Framed within historical pragmatics, this chapter revisits and explains the nature of Portuguese encounters along the western coast of Africa as reported by sailors, missionaries, and merchants. The chapter examines sources written in Portuguese, Dutch, Danish, French, or, later, English. Although Portuguese was used as the trade lingua franca in forts such as Elmina, there is no evidence that it ever pidginized. This disputes the long-held assumption in creolistics that the initial contacts between Europeans and non-Europeans systematically produced pidgins. An important reason is that the use of Portuguese was restricted to the brokers, also known in colonial history as intermediaries, middlemen, and go-betweens. By the seventeenth century, the coastal fortifications were also quite cosmopolitan contact settings where various Europeans speaking different languages and Africans interacted with each other in diverse languages, often without interpreters. Professional interpreters were needed particularly for expensive-commodity transactions. The chapter shows that contact between different populations and “brokers on the move” led to the emergence of new Portuguese varieties in the Cape Verdean archipelago and in Rios de Guiné, just like Portuguese itself had developed from the contact of populations migrating within the former Roman Empire.