Chapter 3 – Conquest of Jamaica

King’s Square, St. Jago de la Vega (Spanish Town) | James Hakewill
A Picturesque Tour of the Island of Jamaica (1825)

Following their abortive attempt to capture Santo Domingo, Penn and Venables were loath to return to England empty-handed and face the Lord Protector. They needed somehow to salvage their professional reputations—they needed a consolation prize. To that end, the English commanders turned their attention to Santiago, the third-largest in the Caribbean, next to Cuba and Hispaniola. By the middle of the 17th century, Santiago had become a relatively insignificant provisioning base that they expected to be thinly peopled and weakly garrisoned.

On 9 May 1655, Admiral Penn’s 38-ship fleet entered Puerto de Caguaya on Santiago’s southeast coast. Penn transferred to William Vesey’s 6th rate Martin, because it drew less water, saying “he would not trust the army if he could come near with his ships.” Other small vessels followed the Martin under the walls of the Caguaya fort (later renamed Passage Fort), which was on the shore of a small bay at the Rio Cobre’s mouth. The larger ships anchored in the harbour. The Martin maintained a brisk cannonade until all ships had disembarked their troops. At this, the Spaniards took flight without waiting for the English to attack.

Venables would not land until he saw that the Spaniards were not resisting. As one source put it: 

“… he continued walking about, wrapped up in his cloak, with his hat over his eyes, looking as if he had been studying of physic more than like the general of an army.”

Venables’ troops had landed about six miles southeast of the capital, Villa de la Vega and—as inefficient as these land forces undoubtedly were—they captured the town from the outnumbered Spaniards on 11 May and the whole island by 17 May. Bad luck and mismanagement continued to plague the invaders, however. The first piece of bad luck came in the form of fishermen sighting the English fleet as it approached Jamaica and setting off the alarm, thereby giving the Spaniards enough time to gather their food and valuables and flee before the English entered the town. By the time Venables’ land force entered Villa de la Vega, the Spanish islanders had fled.  And before leaving, they freed their cattle and other livestock or drove them into the hills. Some of the Spanish planters fled to Cuba, while others withdrew to the mountains with their slaves and continued to resist. 

Soon after taking control of Villa de la Vega and the surrounding area, the English renamed the island “Jamaica” using their form of its original Taíno name, “Xaymaca.” They also renamed the capital “Spanish Town.”

Luck was still not on the side of the invaders, however. On 25 May (according to the Swiftsure’s log), Thomas Wills’ Discovery caught fire in the steward’s room. In time the flames reached her magazine and all her 120 barrels of gunpowder blew up, endangering the Swiftsure, which rode next to her. The loss of the 4th rate Discovery was made greater by the loss of provisions she had onboard. And, only that day, Swiftsure’s lower deck guns had been transferred to her. Fortunately, most of the guns were recovered.

Penn and Venables stayed in Jamaica for a month, overseeing to the pacification of the island and sending cruisers along the Spanish Main. However, since Spain did not have a strong naval presence in the Caribbean, the English land forces did not need a large fleet to defend them. Besides, provisions were running low and had become hard to replenish in Jamaica. Accordingly, the English commanders resolved to return home and take most of the fleet with them, believing the ships would be more useful nearer to home. The ships left in Jamaica were the Torringyton, Martin, Gloucester, Marston Moor, Laurel, Dover, Portland, Grantham, Selby, Hound, Falmouth, and Arms of Holland, with three brigs and a dogger.

Once the capital was in English hands, Penn, hoping to be the first to give his version of events to Cromwell, rushed back to England. When he left Jamaica on 25 Jun, he appointed Vice-Admiral William Goodson as naval Commander. Penn arrived at Spithead on 31 Aug. The ailing Venables followed Penn, arriving in September 1655. Major General Richard Fortescue succeeded Venables as commander of land forces in Jamaica.

Penn and Venables were not warmly welcomed, however. Cromwell stripped them both of their commands for abandoning their posts, and he had them imprisoned in the Tower of London. Their imprisonment was brief, however, and both were released in October 1655 on condition of surrendering their commissions and commands and making the appropriate apologies. Penn withdrew from public life and retired to his estate in Ireland. He died on 16 Sep 1670. Penn’s eldest son was William Penn (1644–1718), the Quaker who founded Pennsylvania.

Venables’s ruined career had a brief revival in 1660 when he was appointed governor of Chester by General Monck. He was soon replaced, however, and retired to Cheshire. In 1662, he published a successful book on angling: The Experienced Angler. He died on 10 Dec 1687.

Together, these men had established Jamaica as a central base at the heart of Spain’s America, from which England could launch attacks. However, the new English colony presented too great a danger to trade routes and treasure ships to be easily abandoned by Spain.

Continued …