Policy makers have long recognized the importance of considering past experience, history, and the use of Analogical reasoning when making policy decisions. When elite political actors face foreign policy crises, they often use their past experience, refer to history, and use Analogical reasoning to help them frame their decisions. In the case of the ill-fated invasion of Cuba at the Bay of Pigs, the use of Analogical reasoning revolving around past covert successes may have created an environment for faulty foreign policy decision-making. Former members of the Office of Strategic Services (OSS) filled the ranks of the Central Intelligence Agency (CIA) and held key positions within the Eisenhower and Kennedy administrations. OSS success with guerrilla warfare, sabotage, and intelligence gathering during World War II, coupled with early CIA covert successes (specifically in Guatemala), may have led President Kennedy to make the wrong policy decisions with regard to dealing with Fidel Castro and Cuba. This research explores the use of Analogical reasoning during the decision-making process by way of process-tracing. Process-tracing attempts to identify the intervening processes between an independent variable (or variables) and the outcome of the dependent variable. We look at six critical junctures and compare how Groupthink, the Bureaucratic Politics Model, and Analogical reasoning approaches help explain any causal mechanisms. The findings suggest that Analogical reasoning may have played a more significant role in President Kennedy's final decision to invade Cuba than previously thought. The findings further suggest that by using the Analogical reasoning approach, our understanding of President Kennedy's foreign policy in Cuba is enhanced when compared to the Groupthink and Bureaucratic Politics Model approaches emphasized in past research.