This chapter interrogates how shifting contexts profoundly impacted Ngugi’s notion of history and his overall vison. Over the years Ngugi’s oeuvre has largely betrayed the conviction that African writing could intervene in the continent’s historiographical pursuits, and also in the actual determination of historical experience. As a result of complications in context, one sees in Ngugi’s later writing an attempt to reinvent himself in the process of interpreting and reinterpreting a perennially confounding postcolonial world in which the writer has been hewn from his history by the realities of migration, exile and globalisation. His later work is characterised by self-reflexivity as he wrestles with and casts doubt on the nature of narratives, especially their position, role or intervention in Africa’s historiography in a context that continues to defy logic. The act of writing is problematised and depicted as emblematic of a contemporary world where the increasing fluidity and unreliable nature of narratives call into question the very notion of historiography. Overall, Ngugi’s later major writing emerges as an epic journey of loss of faith that simultaneously questions, indicts and deconstructs the act of writing in a world where history seems contrived, concocted, deliberately chaotic and even stranger than ever before.