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=== Spanish Colonial era === {{See also|Captaincy General of Puerto Rico}} 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.<ref>{{cite web|title=San Juan National Historic Site|url=http://www.nps.gov/archive/saju/faq.html#3|publisher=National Park Service|year=2000|access-date=2007-05-29|archive-date=March 13, 2012|archive-url=https://web.archive.org/web/20120313142618/http://www.nps.gov/pwr/404.htm#3|url-status=live}}</ref> [[File:Staat van Amerika, map of San Juan, Puerto Rico, 1766.jpg|thumb|San Juan and bay, Puerto Rico, 1766|left]] San Juan underwent 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, 3rd Earl of Cumberland|George Clifford, Earl of Cumberland]], in 1598. Artillery from San Juan's fort, [[Fort San Felipe del Morro|El Morro]], repelled Drake; however, Clifford managed to land troops and lay siege to the city.<ref name="history">{{cite web|title=History of Puerto Rico|publisher=Sol Boricua|year=2000|url=http://www.solboricua.com/history.htm|author=William Figueroa|language=es|access-date=2007-05-02|archive-date=March 6, 2012|archive-url=https://web.archive.org/web/20120306100715/http://www.solboricua.com/history.htm|url-status=live}}</ref> 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 [[Boudewijn Hendricksz|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.<ref>[http://efemerides.zoomblog.com/archivo/2006/09/24/don-Juan-De-Haro-Y-Los-Holandeses-24-d.html "DON JUAN DE HARO Y LOS HOLANDESES" (24 de Septiembre de 1625)] {{webarchive |url=https://web.archive.org/web/20150202024647/http://efemerides.zoomblog.com/archivo/2006/09/24/don-Juan-De-Haro-Y-Los-Holandeses-24-d.html |date=February 2, 2015 }}</ref>{{unreliable source?|date=January 2014}} 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.<ref name="PRH">[http://infomotions.com/etexts/gutenberg/dirs/1/2/2/7/12272/12272.htm The History of Puerto Rico From the Spanish Discovery to the American Occupation / Middeldyk, R.A. Van Identifier: etext12272 The History of Puerto Rico From the Spanish Discovery to the American Occupation] {{webarchive|url=https://web.archive.org/web/20080122112400/http://infomotions.com/etexts/gutenberg/dirs/1/2/2/7/12272/12272.htm |date=January 22, 2008 }}</ref> The British [[Battle of San Juan (1797)|attack]] in 1797, during the [[French Revolutionary Wars]], led by [[Ralph Abercromby|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.
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