In the years immediately prior to, and of, the Second World War textual glimmers of an unnamed Roger Casement can be detected in a preoccupation with the ghostly return of Irish history. As Ireland grappled with what role she could or should play in the (impending) war, a role complicated immeasurably by the precarious border and new Northern statelet, numerous authors grappled with an Irish history compromised by unclear allegiances and betrayal. This chapter uses a collection of mid-twentieth century texts – James Joyce’s Finnegans Wake (1939), Jorge Luis Borges’ ‘The Theme of the Traitor and the Hero’ (1944) and Elizabeth Bowe’s The Heat of the Day (1948) – to map how the interlinking preoccupations of espionage, betrayal and, frequently, sexual intimacy, are deeply connected, implicitly or explicitly, to the haunting spectre of Casement.