Author of Il Regno del Sud (1946), an influential first-hand history of the Kingdom of Italy that was set up in Allied territory after the 1943 armistice, Agostino degli Espinosa did much to shape Italian memory of the Allied occupation of Italy. In this article I examine for the first time degli Espinosa’s doubts about Italy’s postwar future, which appear in the margins of his history, and which come to the fore in his fiction. I argue that the critical re-evaluation of the work of this emblematic but understudied figure can shed light on Italy’s divided memories of the Second World War and the Allied occupation.