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|Battle of San Juan (1625)|
|Part of the Eighty Years' War|
Seventeenth-century Spanish painting commemorating Hendricksz's defeat at San Juan de Puerto Rico. By Eugenio Caxés, Museo del Prado.
|Commanders and leaders|
|Juan de Haro y Sanvitores||Boudewijn Hendricksz|
The Battle of San Juan was fought on 29 September 1625, and was an engagement of the Eighty Years' War. A Dutch expedition under the command of Boudewijn Hendricksz attacked the island of Puerto Rico, but despite besieging San Juan for several months, was unable to capture it from Spain.
On 24 September 1625, 17 Dutch ships arrived at San Juan de Puerto Rico, whose Spanish governor — naval and military veteran Juan de Haro y Sanvitores — had been in office less than a month. Nevertheless, he got ready to receive the enemy as best he could preparing El Morro's battery to close the main entrance to the San Juan Bay, and sending his predecessor, Juan de Vargas, to nearby Boquerón with militia to hinder any landings in the Escambrón Inlet.  
Hendricksz implemented a bold plan. At 1:00 P.M. the next day the entire Dutch fleet sailed directly into San Juan’s harbor:
Roode Leeuw, Witte Leeuw, Leyden, Blauwe Leeuw, Goude Valck, Utrecht, Nieuw Nederlandt, Hoop van Dordrecht, Kleyne Tijger, Hoorn, Medemblik, Gouden Molen, Vlissingen, West Kappel, Goude Sonne, Koningin Hester, and Jonas.
They exchanged shots with the harbor castle, inflicting superficial damage and killing four Spaniards, before gaining a safe anchorage within the roadstead off Puntilla Point, beyond range of de Haro’s artillery. However, shoals prevented an immediate disembarkation of troops. The delay allowed Spanish civilians to flee inland, while the governor marshaled his slender strength within San Felipe del Morro citadel. He installed six additional bronze 12-pounders in its embrasures and mustered 330 men, of which 220 were effective. He also had abundant supplies.
On 26 September, Hendricksz led 700–800 men ashore and occupied the empty city. Two days later the Dutch also occupied the small, wooden El Cañuelo fort, which stood on a rock islet in the harbour. The main citadel proved impossible to storm, so the Dutch began digging saplines and installing a six-gun battery atop Calvario Heights by 29 September. At 9:00 A.M. the next day Hendricksz called upon de Haro to surrender. de Haro rejected the offer so action resumed. Capt. Jan Jasperz de Laet of West Kappel exited the harbour on 1 October to chase away a Spanish ship arriving with supplies. On the night of Friday, 3–4 October, the Spaniards sallied out of their citadel in two companies of 40 men apiece under Capts. Sebastián de Avila and Andrés Botello, but accomplished little.
They enjoyed better fortune at noon on 5 October, when 50 men under Capt. Juan de Amézqueta y Quixano of the Puerto Rican militia destroyed the advance Dutch works, killing a captain, a sergeant, and eight sappers. Guerrillas from the interior under Capt. Andrés Vázquez Botello de Carrera also began plaguing the besiegers. On the night of 5 October they killed Nieuw Nederlandt’s captain and a 20-man boat party in the harbor. Ten days later they destroyed a similar force up Bayamón River.
By October 16 the guerrillas had grown so bold as to recapture El Cañuelo. A force of 30 men in two launches arrived and killed two of its Dutch occupiers, capturing another 14. Faced with this increased pressure, Hendricksz found himself trapped inside the harbor. He again called upon de Haro to capitulate on 21 October, threatening to burn the city, but was again rebuffed. Hendricksz then put San Juan to the torch, and the Dutch reembarked at 10:00 A.M. the next day, hotly pursued by Puerto Rican units. The invaders now had to run the gauntlet of Spanish artillery in order to escape, which led them to hesitate for a full fortnight before they finally fled on 2 November.
The 30-gun, 450-ton Medemblik ran aground and was left behind for the exultant Spanish. Juan de Amézqueta boarded her and extinguished the slow fuse that was burning toward her magazine. De Haro was unable to savor the victory because a cannon had exploded near him during these final exchanges, spraying him with two dozen fragments that eventually killed him. Hendricksz, meanwhile, retired to San Francisco Bay for a month to recover from the setback. In addition to the loss of Medemblik, numerous other Dutch vessels had sustained damage, and 200 men have perished (as opposed to 17 Spanish fatalities during the siege). Hendricksz nonetheless detached his five best vessels on a privateering cruise toward Santo Domingo before attempting to lead his entire fleet west again in late November. Driven back by storms, he cruised south toward Isla Margarita (Venezuela), despite advance warnings having preceded him.
- Lane, Kris (2015). Pillaging the Empire: Global Piracy on the High Seas, 1500-1750. Routledge. p. 62. ISBN 1317524470.
- Government Printing Office (1996). Forts of Old San Juan: San Juan National Historic Site, Puerto Rico. DC: Government Printing Office. p. 43. ISBN 091262762X.
- David F. Marley. Wars of the Americas: A Chronology of Armed Conflict in the New World, 1492 to the Present ABC-CLIO(1998) ISBN 0-87436-837-5
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