The role of American intelligence in the Cuban missile crisis is crucial to understanding perceptions and judgements of key actors in October 1962. Dino Brugioni’s Eyeball to Eyeball provides a detailed ‘insider’s’ account that combines memoir and history. It focuses on the role of aerial intelligence which was vital to how the crisis was managed in Washington. Brugioni’s account also provides a representation of events that explores both military/operational aspects and political decision-making in Washington most importantly that of President John F. Kennedy. Brugioni argues that was a victory for Kennedy and for America. Twenty years of scholarship and revelation have challenged this conclusion, a conclusion which this article examines. Likewise the idea that the crisis marked a notable success for the CIA is revisited in the light of new information and assessments.