This article tests the predictions of expected-utility and prospect theories against the most important dimensions of the Cuban missile crisis. Largely through use of the most recently released information on the crisis from the American and Soviet governments, I attempt to ascertain the anticipated benefits, costs, and probabilities of success associated with each of the major policy choices that the key leaders in both superpowers perceived before each of the major decisions throughout the crisis was made. Using this information and the logic of extensive-form game-theoretic models of choice, I construct a baseline for expected-utility theory that helps us to understand when prospect or expected-utility theory provides the better explanation for a particular decision. Prospect theory predicts that when individuals perceive themselves to be experiencing losses at the time they make a decision, and when their probability estimates associated with their principal policy options are in the moderate to high range, they will tend to make excessively risky, non–value maximizing choices. I find that the evidence for the Cuban missile crisis supports this prediction for the most important decisions made by both Khrushchev and Kennedy.