This book examines U.S.-Cuba relations within the framework of the U.S.'s long-standing policy agenda of promoting a democratic transition in Cuba. The study builds a theoretical framework which is used to analyze the assumptions underlying the U.S. strategy. It presents a rich empirical analysis that gives insight into the U.S. policies which produced neither the collapse of the Cuban regime nor a transition to democracy. It is examined using a theoretical framework and an empirical analysis from both a top-down and a bottom-up approach.