The paper explores the role of secret intelligence in literature and society and its role in both promoting and threatening freedom. Ranging from the Cold War to the ‘war on terror’, this paper gives prominence to ‘the spying game’ with special reference to the Asia-Pacific region. What are the perils and pleasures of spying? How do spies resolve the moral dilemmas of the ‘second oldest profession’? What freedoms do they enjoy? What constraints? How does their work impinge on the freedoms of others? Novels by David Malouf, Nicholas Hasluck, Janette Turner Hospital, Brian Castro and Christopher Koch provide insight into these questions while drawing readers into their webs of intrigue.