San Juan, a settlement of the Spanish Empire

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In 1508, Juan Ponce de León founded the original settlement Caparra (named after the province Caceres, Spain, the birthplace of then-governor of Spain's Caribbean territories Nicolas de Ovando), which today is known as the Pueblo Viejo sector of Guaynabo, just to the west of the present San Juan metropolitan area.

A year later, the settlement was moved to a site then called Puerto Rico, Spanish for "rich port" or "good port," after its similar geographical features to the island of Gran Canaria in the Canary Islands. In 1521, the newer settlement was given its formal name, San Juan Bautista de Puerto Rico, in honor of John the Baptist, following the tradition of christening the town with both its formal name and the name which Christopher Columbus had originally given the island.

The ambiguous use of San Juan Bautista and Puerto Rico for calling both the city and the island led to a reversal in practical use by most inhabitants: by 1746, the name for the city (Puerto Rico) had become that of the entire island, while the name for the Island (San Juan Bautista) had become the name for the city.

La Puerta de San Juan (San Juan Gate)

San Juan, as a settlement of the Spanish Empire, was used by merchant and military ships traveling from Spain as the first stopover in the Americas. Because of its prominence in the Caribbean, a network of fortifications was built to protect the transports of gold and silver from the New World to Europe. Because of the rich transports, San Juan became a target of the foreign powers of the time.

The city was witness to attacks from the English led by Sir Francis Drake in 1595 and by George Clifford, Earl of Cumberland, in 1598. Artillery from San Juan's fort, El Morro, repelled Drake; however, Clifford managed to land troops and lay siege to the city.^[10] After a few months of British occupation, Clifford was forced to abandon the siege when his troops began to suffer from exhaustion and sickness. In 1625 the city was sacked by Dutch forces lead by Boudewijn Hendricksz, but El Morro withstood the assault and was not taken. The English attacked again in 1797, during the French Revolutionary Wars, led by Sir Ralph Abercromby (who had just conquered Trinidad). His army laid siege to the city but was forced to withdraw in defeat as the Puerto Rican defenses proved more resilient than those of Trinidad. Various events and circumstances, including liberalized commerce with Spain, the opening of the island to immigrants as a direct result of the Royal Decree of Graces of 1815, and the colonial revolutions, led to an expansion of San Juan and other Puerto Rican settlements in the late 18th and early 19th century.

In May 1898, United States Navy ships, among them the USS Detroit, USS Indiana, USS New York, USS Amphitrite, USS Terror and USS Montgomery, commanded by Rear Admiral William T. Sampson, bombed San Juan during the Spanish-American War, though the city was not occupied. On July 25, General Nelson A. Miles landed at Guánica (in southwestern Puerto Rico) with 3,300 soldiers and took over the island with little resistance. Spain ceded the island to the United States later the same year by signing the Treaty of Paris.

Camp Las Casas, located in the district of Santurce, served as the main training camp for the Puerto Rican soldiers prior to World War I and World War II; the majority of the men trained in this facility were assigned to the 65th Infantry Regiment of the United States Army. This regiment has been active since 1898, and it is still active today. Camp Las Casas was eventually closed down, and in 1950 a public housing project by the name of Residencial Fray Bartolome de Las Casas was constructed on its former location.

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