Starting on the eve of the arrival of Columbus and ending with the 2020 US presidential election, this book provides us with a front-row seat as we witness the evolution of modern Cuba, with its dramatic history of conquest and colonization, of slavery and freedom, of independence and revolutions made and unmade. Throughout, Ferrer explores the sometimes surprising, often troubled intimacy between Cuba and its neighbor to the north, documenting not only the influence of the United States on Cuba but also the many ways Cuba has been a recurring presence in US affairs.