This chapter explores the antecedents to colonization and empire, central to the story of Britain’s relationship with Africa from the first century to the mid-twentieth century. The earliest relationships with Africa emerge from encounters between the British Isles and the foreign powers that invaded them: the Romans, Vikings and Normans. Further, how these foreign powers (as crown/state) administered the British Isles had an enduring influence on the character of British venturing and colonizastion. Moreover, on-going rivalries with European nations further shaped Britain’s crown/state policy towards trade, then imperialism, in Africa. Commercial venturing, and eventually military expedition-based venturing companies, were key to the Britain’s economic colonial and economic presence in Africa. We therefore explore the role of crown/state sponsorship of merchants and venturers. This evolution and dynamics of encounters between Britain and Africa can be captured theoretically through Michel Foucault’s concept of the heterotopia. As a final counter point to the often positive mid-twentieth accounts of the legacies of colonialism, the losses, from the perspective of Africans, is understood through Amartya Sen’s historical analysis of the contemporaneous and enduring negative impacts of colonialism.