The United States has shared an intricate and turbulent history with Caribbean islands and nations since its inception. In its relations with the Caribbean, the United States has displayed the dueling tendencies of imperialism and anticolonialism that characterized its foreign policy with South America and the rest of the world. For nearly two and a half centuries, the Caribbean has stood at the epicenter of some of the US government’s most controversial and divisive foreign policies. After the American Revolution severed political ties between the United States and the British West Indies, US officials and traders hoped to expand their political and economic influence in the Caribbean. US trade in the Caribbean played an influential role in the events that led to the War of 1812. The Monroe Doctrine provided a blueprint for reconciling imperial ambitions in the Caribbean with anti-imperial sentiment. During the mid-19th century, Americans debated the propriety of annexing Caribbean islands, especially Cuba. After the Spanish-American War of 1898, the US government took an increasingly imperialist approach to its relations with the Caribbean, acquiring some islands as federal territories and augmenting its political, military, and economic influence in others. Contingents of the US population and government disapproved of such imperialistic measures, and beginning in the 1930s the US government softened, but did not relinquish, its influence in the Caribbean. Between the 1950s and the end of the Cold War, US officials wrestled with how to exert influence in the Caribbean in a postcolonial world. Since the end of the Cold War, the United States has intervened in Caribbean domestic politics to enhance democracy, continuing its oscillation between democratic and imperial impulses.