Early settlement

For 15 years San Juan Bautista was neglected except for an occasional visit by a ship putting in for supplies. In 1508 Juan Ponce de León, who had accompanied Columbus and worked to colonize Hispaniola, was granted permission to explore the island. On the north coast Ponce de León found an exceptionally well-protected bay that could harbour a large number of sailing vessels; on high ground beside the bay he founded Caparra, the island’s first town and the site of its first mining and agricultural operations. By 1521 the town was moved to an islet at the northern end of the harbour and renamed Puerto Rico (“Rich Port”). Through time and common usage the port became known as San Juan while the name Puerto Rico came to be applied to the whole island.

The Taino soon lost reverence for their Spanish “protectors,” who expected the Indians to act as vassals, paying tribute in gold and food as well as accepting instruction in the Christian religion. Meanwhile, European diseases (to which the Spaniards were largely immune) and maltreatment had begun to devastate the Taino population. In 1511 the Indians rebelled but had only temporary success against the better-armed Spanish, who again subjugated them. The Spanish subsequently brought Indian slaves from nearby islands and black slaves from Africa in order to fully staff their placer mines. However, gold production markedly declined after the 1530s, and many of the Europeans migrated elsewhere.

Those who remained set up sugarcane and ginger plantations with their African slaves, but the colony continued to lead a precarious existence. Carib groups from neighbouring islands made frequent raids, carrying off food and slaves and destroying property. Puerto Rico was further ravaged by disease, and it was plundered by French, British, and Dutch pirates. During the mid-16th century French forces repeatedly burned and sacked San Germán, the island’s second settlement. Increasing numbers of colonists left the island.

In the second half of the 16th century Spain, recognizing the strategic importance of Puerto Rico, undertook to convert San Juan into a military outpost by using a financial subsidy from the Mexican mines. Initially they built a fortified palace for the governor called La Fortaleza (“The Fortress”), followed by the massive San Felipe del Morro (El Morro) castle, which was perfectly located to dominate the narrow entrance to the harbour. Finally they added a stronger and larger fortress (San Cristóbal) to the northeast, on the Atlantic side of the city. In the early 17th century the city was surrounded by a stone wall 25 feet (8 metres) high and 18 feet (5 metres) thick, two parts of which still stand. These defenses made San Juan almost impregnable.

In 1595 Sir Francis Drake attacked the city with a sizable fleet but failed to silence its guns. Three years later the British soldier George Clifford, 3rd earl of Cumberland, captured the city but was soon forced to abandon it after his troops fell victim to disease (probably dysentery). In 1625 the Dutchman Bowdoin Hendrik captured and burned the town but failed to subdue El Morro, where the governor had taken refuge.

San Juan, the most exposed military outpost guarding Spain’s New World empire, received political and economic attention from the mother country; however, the island’s rural inhabitants, or jíbaros, were typically ignored by Spain and scorned by the residents of San Juan. The jíbaros thus fended for themselves and cultivated their own small landholdings. As the French, British, Danish, and Dutch fought over and settled the Lesser Antilles during the 17th and 18th centuries, the colonial authorities of San Juan rarely ventured beyond their walled defenses for fear of buccaneer attacks; however, the jíbaros, ignoring the edicts of Spain, prospered somewhat by trading clandestinely with non-Spanish merchants. Ginger, hides, sugarcane, tobacco, and cattle from the island were in great demand. The settlers’ contact with foreigners did not turn them away from their mother country—as the Spanish crown had feared—instead, they remained loyal and willing to participate in military expeditions.