The history of Puerto Rico began with the settlement of the archipelago of Puerto Rico by the Ortoiroid people between 3000 and 2000 BC. Other tribes, such as the Saladoid and Arawak Indians, populated the island between 430 BC and 1000 AD. At the time of Christopher Columbus's arrival in the New World in 1492, the dominant indigenous culture was that of the Taínos. The Taíno culture died out during the latter half of the 16th century because of exploitation by Spanish settlers, the war they waged on the Taíno, and diseases introduced by the invaders.

Located in the northeastern Caribbean, Puerto Rico formed a key part of the Spanish Empire from the early years of the exploration, conquest and colonization of the New World. The island was a major military post during many wars between Spain and other European powers for control of the region in the 16th, 17th and 18th centuries. The smallest of the Greater Antilles, Puerto Rico was a stepping-stone in the passage from Europe to Cuba, Mexico, Central America, and the northern territories of South America. Throughout most of the 19th century until the conclusion of the Spanish–American War, Puerto Rico and Cuba were the last two Spanish colonies in the New World; they served as Spain's final outposts in a strategy to regain control of the American continents.

In 1898, during the Spanish–American war, Puerto Rico was invaded and subsequently became a possession of the United States. The first half of the 20th century was marked by the struggle to obtain greater democratic rights from the United States. The Foraker Act of 1900, which established a civil government, and the Jones Act of 1917, which made Puerto Ricans U.S. citizens, paved the way for the drafting of Puerto Rico's Constitution and the establishment of democratic elections in 1952. However, the political status of Puerto Rico, a Commonwealth controlled by the United States, remains an anomaly more than 500 years after the first Europeans settled the island.