Jamaican History & Culture – English Conquest


On 10 May 1655, an English fleet of 38 ships and 8,000 men anchored in Caguaya Bay, the landing place for Villa de la Vega, the capital of Santiago. The Spanish colony, thinly populated and weakly defended, was no match for so large an invasion force. Santiago is, of course, the West Indian island we know as Jamaica. Caguaya Bay, as it was known to the Taíno and Spanish, was renamed Cagway Bay (later, Port Royal) by the English in 1655.

The Lord Protector of England, Oliver Cromwell, was given to believe the Spanish colony of Hispaniola was weakly defended and could be taken easily. So he sent an expeditionary force to secure a base of operations in the Spanish West Indies from which to strike at the Spanish Main and weaken Roman Catholic influence in the New World. Cromwell appointed Robert Venables as the General Commander of land forces. And he appointed General-at-Sea William Penn as the commander of the naval force.  William Penn was the father of William Penn, who founded Pennsylvania. While both were experienced and competent officers, neither was given the expedition’s overall command—an oversight that would prove unwise.

Admiral Sir William Penn (1621–1670)
Admiral Sir William Penn, 1621–1670
by Sir Peter Lely

A fleet of eighteen warships and twenty transport vessels set sail from Portsmouth on Christmas Day of 1654, arriving at Barbados a month later, where a significant number of additional troops were recruited. Their numbers were impressive on paper, but the recruits were untrained and lacked military discipline. Furthermore, supplies were already running low, and friction was developing between the joint commanders Penn and Venables. By the way, among those accompanying General Venables’s forces was a young Welshman named Henry Morgan. I’ll have more to say about that young man later in this story.

Morale suffered when troops were ordered not to plunder Spanish settlements because the English authorities wished to capture them intact for later colonization.

On 13 April 1655, the fleet arrived off Santo Domingo, the main settlement on Hispaniola. Weather prevented them from landing close to the town, however. Therefore, the English forces had to land some twenty-five miles west of Santo Domingo, a three-day march away. Thus, any hopes of surprising the Spanish defenders were dashed, since the colonists had time to reinforce their defences and prepare for the impending assault.

The expeditionary force was not well equipped for the terrain they encountered—water bottles had not been provided, for example—and the English suffered greatly from heat and lack of fresh water. Many fell ill, including General Venables. When they did reach Santo Domingo, they were ambushed and almost routed before the general ordered a withdrawal. The Englishmen remained onshore for about a week trying to recover for many were sick and most were without shelter or adequate supplies.

On 24 April, with Penn’s fleet bombarding the town from the sea, Venables led a second land assault on Santo Domingo. However, another Spanish ambush ended that land attack. So, recognizing their expedition had become a dismal failure, its commanders agreed to abandon any further attempt on Hispaniola. Returning to England and facing Cromwell empty-handed was an unattractive prospect, however. So Penn and Venables desperately needed somehow to salvage the situation and their damaged reputations. Thus they sought an easier target. 

This, Penn and Venables decided, would be the neighbouring island of Jamaica, which had by that time declined to the point that it was an insignificant provisioning base. They needed to give the Lord Protector a “consolation prize,” and Jamaica would fit the bill.

The English force captured Jamaica with ease—except for an area on its north side. It was there that the Spanish governor with most of the Spanish planters and their slaves had retired to wage a guerilla war against the invaders.

Jamaica—as a central base from which the English could launch attacks on Spanish trade routes and treasure ships—presented too much of a danger to Spain to allow it to be abandoned. So, from 1655 to 1660, Spanish forces led by Governor Don Cristobal Arnaldo Ysassi made several unsuccessful attempts to recapture the island. Small bands of Spanish soldiers landed from time to time to reinforce Yssasi. They came from Havana, San Domingo and Porto Rico and were joined by Spanish refugees from Jamaica who had fled earlier to Santiago de Cuba.

The most important battle ever fought on Jamaican soil took place at Rio Neuvo in June 1658 when the English commander and new governor Colonel Edward D’Oyley defeated a large force under Ysassi’s command.

The English killed more than 300 Spaniards and captured great quantities of food and arms. Ysassi withdrew to the hillsides and jungles on the north side of the island with his force’s survivors. And, although he continued to wage guerilla warfare for several more months, by 1660, the Spaniards had had enough. Ysassi, with his remaining supporters, fled by canoe to Cuba.

Here’s how historian Brig. General E.A. Cruikshank described those last days:

After enduring an extremity of hardship, hunger, and privation, Yssasi’s worst forebodings were fulfilled. On the 26th of February, 1660, Lieut.-Colonel Tyson with a party of only eighty men, guided over the mountains by some of these negroes, surprised his camp at Rio Hoja, near Moneague, killed his chief lieutenant and fifty others, took a few prisoners, and dispersed the rest of his men beyond recall. The English leader reported that Yssasi ‘ran so nimbly as to save himself from being taken.’
Negotiations were begun for a treaty of surrender, but failed. A boat bringing supplies from Cuba was captured in the bay of Ocho Rios, making further resistance all but hopeless. Two large canoes were fashioned out of cottonwood logs, sails were improvised from hunters’ sheets, Yssasi embarked with his remaining adherents at the little harbour, which has ever since been known as Runaway Bay, and safely crossed the hundred miles of tranquil water that separated him from Cuba. Spanish dominion over any part of Jamaica had come to an end. Some hundreds of impoverished fugitives found an asylum at Bayano, Santiago, and Trinidad, where they obtained lands and continued for the next ten years to cherish hopes of regaining their lost possessions, and form fruitless plans for that object.

In 1670, under the Treaty of Madrid, Spain officially ceded control of Jamaica and the Cayman Islands to England. It is interesting to note that before the English conquest, Jamaica was the property of Don Pedro Colon de Portugal y Castro, Duke of Veragua & La Vega, 1st Marquis of Jamaica, 7th descendant of Christopher Columbus. (The property rights of Columbus’s family that pertained to Jamaica had been recognized in 1508.) This, I gather, is why the Inquisition (Inquisición española) was never fully enforced in Jamaica. And, as a result, when the English captured the island in 1655, there where considerable numbers of Jews—known variously as “Portugals,” “Sephardim,” and “Marranos”—already settled in the Island. Many, perhaps most, were conversos who converted to Catholicism under threat. And some continued to practice Judaism in secret.

King Charles II of England
by Peter Lely
Collection of Euston Hall Suffolk
The English welcomed the Jews and considered them an integral part of the colony. The Jews were granted citizenship by Oliver Cromwell, and King Charles II confirmed this in 1660. Citizenship was important to the Jews, for it entitled them to own property. (Note that in those times, many Jews living in Europe were never granted citizenship there.) And perhaps most important of all, under English rule, Jamaican Jews could practice their religion openly.

Before fleeing the island, the Spaniards armed and freed their slaves, but not before terrifying them with stories about the “man-eating English.” The slaves they left behind were expected to continue the guerrilla war against the English until their Spanish masters could return and recapture the island. These freed slaves joined other runaway slaves in the mountains and became the semi-autonomous nation we know as Jamaican Maroons.

Penn and Venables left Jamaica soon after its capture, returning separately to England. Because both officers had left Jamaica without orders, they were relieved of their commands and immediately committed to the Tower of London. Venables was released after a brief stay, on condition he surrender his general’s commission and command in Ireland. Penn was also released, and he retired to his estate in Ireland.

It is important to remember that back then, many English people were convinced that Spain was a cruel and merciless enemy. Oliver Cromwell proclaimed this very notion in his speech to Parliament on  17 Sep 1656. “Abroad, our great enemy is the Spaniard,” he said. To him, conflict with Spain was a just and holy war. Cromwell intended Jamaica to be England’s base of operations against the Spaniards, both by land and sea.

Meanwhile, the English forces remaining in Jamaica were suffering from a shortage of supplies and low morale. Many were ill from dysentery and fevers. Famine threatened. Despite such difficulties, the new masters of Jamaica set about consolidating their victory. In the weeks following the conquest, priority became defence against recapture. Construction of Passage Fort, also known as Fort Cromwell, began at the tip of the sand spit, separating what is now called Kingston Harbour from the Caribbean Sea. From that location, the fort could control all access to the harbour through its narrow entrance.

After Christopher Columbus landed in the Bahamas in 1492, the Spanish term Antillas applied to the lands he “discovered,” and “Sea of the Antilles” became a common alternative name for “Caribbean Sea” in various European languages. By the 16th century, however, the name most commonly used by Europeans was the “North Sea.” Of course, the “South Sea” was the Pacific Ocean. Penn and Venables would certainly have use the name “North Sea.”

Soon a small community, known as The Point or Cagway Bay, would grow up around the fort. The name of the town would be changed to Port Royal, and the fort would be renamed Fort Charles in 1660 in honour of the restoration of Charles II and the English monarchy.

Soldiers were encouraged to cultivate the land plots that had been allotted to them. The small naval squadron stationed there would keep busy by capturing valuable prizes and bringing them into Cagway Bay (Port Royal). Thus began England’s—and later the United Kingdom’s—300-year rule of Jamaica.