When U.S. immigration authorities deported Graham Greene from Puerto Rico in 1954, the British author made an unplanned visit to Havana and the former MI6 officer had stumbled upon the ideal setting for a comic espionage story. Three years later, he returned in the midst of Castro’s guerrilla insurgency against a U.S.-backed dictator to begin writing his iconic novel . Twelve weeks after its publication, in January 1959, the Cuban Revolution triumphed, soon transforming a capitalist playground into a communist stronghold. Combining biography, history, politics, and a measure of psychoanalysis, investigates the real story behind Greene’s fiction. It includes his many visits to a pleasure island that became a revolutionary island, turning his chance involvement into a political commitment. His Cuban novel describes an amateur agent who dupes his intelligence chiefs with invented reports about “concrete platforms and unidentifiable pieces of giant machinery.” With eerie prescience, Greene’s satirical tale had foretold the Cold War’s most perilous episode, the 1962 Cuban Missile Crisis. Exploiting a wealth of archival material and interviews with key protagonists, delves into the story behind and beyond the author’s prophetic Cuban tale, focusing on one slice of Greene’s manic life: a single novel and its complex history.