Today, San Juan is Puerto Rico's most important seaport, and is the island's manufacturing, financial, cultural, and tourism center. The population of the Metropolitan Statistical Area, including San Juan and the municipalities of Bayamón, Guaynabo, Cataño, Canóvanas, Caguas, Toa Alta, Toa Baja, Carolina and Trujillo Alto, is about 2 million inhabitants; thus, about half the population of Puerto Rico now lives and works in this area. San Juan is also a principal city of the San Juan-Caguas-Fajardo Combined Statistical Area. The city has been the host of events within the sports community, including the 1979 Pan American Games, 1966 Central American and Caribbean Games, events of the 2006, 2009 and 2013 World Baseball Classics, the Caribbean Series and the Special Olympics and MLB San Juan Series in 2010.
In 1508, Juan Ponce de León founded the original settlement which he called Caparra. It was named after the Province of Cáceres in Spain, the birthplace of Nicolás de Ovando, then the Governor of Spain's Caribbean territories, Today it is part of 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 town of Puerto Rico of Gran Canaria in the Canary Islands. In 1521, the newer settlement was given its formal name, Puerto Rico de San Juan Bautista.
The ambiguous use of San Juan Bautista and Puerto Rico for both the city and the island in time 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, leading to the city being identified as Puerto Rico de Puerto Rico on maps of the era.
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 cargoes, 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 (in what is known as the Battle of Puerto Rico) 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. After a few months of English 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 led by Captain Balduino Enrico (also known as Boudewijn Hendricksz/Bowdoin Henrick), but El Morro withstood the assault and was not taken. The Dutch were counterattacked by Captain Juan de Amézqueta and 50 members of the civilian militia on land and by the cannons of the Spanish troops in El Morro Castle. The land battle left 60 Dutch soldiers dead and Enrico with a sword wound to his neck which he received from the hands of Amézqueta. The Dutch ships at sea were boarded by Puerto Ricans who defeated those aboard. After a long battle, the Spanish soldiers and volunteers of the city's militia were able to defend the city from the attack and save the island from an invasion. On October 21, Enrico set La Fortaleza and the city ablaze. Captains Amézqueta and Andrés Botello decided to put a stop to the destruction and led 200 men in an attack against the enemy's front and rear guard. They drove Enrico and his men from their trenches and into the ocean in their haste to reach their ships.