This chapter employs the transnational as the operative framework to analyse various literary representations of a Malay historical figure who was christened Enrique by the Portuguese circumnavigator Ferdinand Magellan in the sixteenth century, which was a period of European colonial expansion in Southeast Asia. Contemporary novels engage an imaginative reworking of Enrique’s personal life and historical times in this early colonial period. Briefly discussing Harun Aminurrashid’s Panglima Awang (1958) and Carla M. Pacis’ Enrique El Negro (2002), this chapter will focus mainly on examining the fictionalisation of Enrique in Danny Jalil’s Enrique the Black (2021). The Malay protagonist’s transnational migration and mobility can be seen to facilitate his learning and unlearning of a colonial and Orientalist discourse of his Malay identity. Economic and cultural globalisation have led to transnational contestations of race and religion in Southeast Asia, including the Malay and Muslim identities of Enrique. By analysing his transnational travels, a critique of colonial and post-postcolonial transnational processes of globalisation is observed in the literary renderings of Enrique’s experiences of traversing national boundaries and cultural landscapes that produce in him a sense of shifting homes.