Hubert Jennings's Lisbon memoirs bring something new to the study of Fernando Pessoa. This article reads Pessoa through the eyes of Jennings and situates both in the context of British decolonization, Portuguese colonial warfare, Commonwealth immigration, and 1960s political upheavals – in order to better understand their differential implication in imperialist ideologies. Close reading of these memoirs reveals a Jennings who identifies himself with Pessoa's ways of seeing, feeling, thinking, and writing. These multiple convergences in effect bear out Pessoa's prophecies of the coming of a new Portuguese cultural empire that would spread across the globe. At the same time, Jennings's residence in Lisbon, in an era when the British and Portuguese empires were receding, triggered nostalgia for the imperial England of his youth. An unpublished short story by Jennings and Chapter V of his memoirs are presented as annexes