In late 1654, English leader Oliver Cromwell launched the Western Design armada against Spain's colonies in the Caribbean. In April 1655, General Robert Venables led the armada in an attack on Spain's fort at Santo Domingo, Hispaniola. However, the Spanish repulsed this poorly-executed attack, known as the Siege of Santo Domingo, and the English troops were soon decimated by disease.
Weakened by fever and looking for an easy victory following their defeat at Santo Domingo, the English force then sailed for Jamaica, the only Spanish West Indies island that did not have new defensive works. Spanish Jamaica had been a colony of Spain for over a hundred years. In May 1655, around 7,000 English soldiers landed near Jamaica's Spanish Town capital. The English invasion force soon overwhelmed the small number of Spanish troops (at the time, Jamaica's entire population only numbered around 2,500).
In the following years, Spain repeatedly attempted to recapture Jamaica, and in response in 1657 the English Governor of Jamaica invited buccaneers to base themselves at Port Royal on Santiago, to help defend against Spanish attacks. Spain never recaptured Jamaica, losing the Battle of Ocho Rios in 1657 and the Battle of Rio Nuevo in 1658. Governor Edward D'Oyley succeeded in persuading one of the leaders of the Spanish Maroons, Juan de Bolas, to switch sides and join the English along with his Maroon warriors. In 1660, when Don Cristobal de Ysasi realised that de Bolas had joined the English, he admitted that the Spanish no longer had a chance of recapturing the island, since de Bolas and his men knew the mountainous interior better than the Spanish and the English. Ysasi gave up on his dreams, and fled to Cuba.
For England, Jamaica was to be the 'dagger pointed at the heart of the Spanish Empire,' although in fact it was a possession of little economic value then.
Early British colonisation
Cromwell increased the island's white population by sending indentured servants and prisoners captured in battles with the Irish and Scots, as well as some common criminals. This practice was continued under Charles II, and the white population was also augmented by immigrants from the North American mainland and other islands, as well as by the English buccaneers. But tropical diseases kept the number of whites well under 10,000 until about 1740. The white population increased, through migration from Britain, to 80,000 in the 1780s.
Although the slave population in the 1670s and 1680s never exceeded roughly 9,500, by the end of the seventeenth century imports of slaves increased the black population to at least three times the number of whites. In the eighteenth century, the population of black slaves in Jamaica increased significantly from one decade to the next, despite the fact that the slave ships coming from the west coast of Africa preferred to unload at the islands of the Eastern Caribbean. At the beginning of the eighteenth century, the number of slaves in Jamaica did not exceed 45,000, but this population rose to about 75,000 in 1730, and passed the 100,000 mark in the 1740s. In 1778, the black slave population passed 200,000, and by 1800 it had increased to over 300,000.
Beginning with the Stuart monarchy's appointment of a civil governor to Jamaica in 1661, political patterns were established that lasted well into the twentieth century. The second governor, Lord Windsor, brought with him in 1662 a proclamation from the king giving Jamaica's non-slave populace the rights of English citizens, including the right to make their own laws. Although he spent only ten weeks in Jamaica, Lord Windsor laid the foundations of a governing system that was to last for two centuries: a Crown-appointed governor acting with the advice of a nominated council in the legislature. The legislature consisted of the governor and an elected but highly unrepresentative House of Assembly.
England gained formal possession of Jamaica from Spain in 1670 through the Treaty of Madrid. Removing the pressing need for constant defence against Spanish attack, this change served as an incentive to planting. For years, however, the planter-dominated Jamaica House of Assembly was in continual conflict with the various governors and the Stuart kings; there were also contentious factions within the assembly itself. For much of the 1670s and 1680s, Charles II and James II and the assembly feuded over such matters as the purchase of slaves from ships not run by the royal English trading company. The last Stuart governor, the Duke of Albemarle, who was more interested in treasure hunting than in planting, turned the planter oligarchy out of office. After the duke's death in 1688, the planters, who had fled Jamaica to London, succeeded in lobbying James II to order a return to the pre-Albemarle political arrangement and the revolution that brought William III and Mary to the throne in 1689 confirmed the local control of Jamaican planters belonging to the Assembly. This settlement also improved the supply of slaves and resulted in more protection, including military support, for the planters against foreign competition. This was of particular importance during the Anglo-French War in the Caribbean from 1689 to 1713.
However, even though the Spaniards no longer threatened Jamaica, the early English settlers had to ward off attacks from the French. In 1694, Jean-Baptiste du Casse led a force of three warships and 29 transport ships that landed at Port Morant in eastern Jamaica, where they burnt plantations, destroyed over 50 sugar-works, kidnapped hundreds of slaves, and killed and tortured many white colonists. Du Casse then sailed down the southern coast, eventually landing at Carlisle Bay, with the object of marching on to Spanish Town. However, a militia company of planters and their slaves defeated du Casse, who then destroyed Carlisle Bay, and withdrew to St Domingue.
The sugar monoculture and slave-worked plantation society spread across Jamaica throughout the eighteenth century.
When the British captured Jamaica in 1655, the Spanish colonists fled, leaving a large number of African slaves. These former Spanish slaves created three Palenques, or settlements. Former slaves organised under the leadership of Juan de Serras allied with the Spanish guerrillas on the western end of the Cockpit Country, while those under Juan de Bolas established themselves in modern-day Clarendon Parish, Jamaica and served as a "black militia" for the English. The third chose to join those who had previously escaped from the Spanish to live and intermarry with the Arawak people. Each group of Jamaican Maroons established distinct independent communities in the mountainous interior of Jamaica. They survived by subsistence farming and periodic raids of plantations. Over time, the Maroons came to control large areas of the Jamaican interior.
Throughout the seventeenth century, and in the first few decades of the eighteenth century, the Maroons took a heavy toll on the British troops. The English colonial authorities sent local militia and English army units against them, but the Maroons successfully fought a guerrilla campaign against them in the mountainous interior, and forced the British government to seek peace terms to end the expensive conflict. In the second half of the seventeenth century, de Serras fought regular campaigns against the English forces, even attacking the capital of Spanish Town, and he was never defeated by the English.
In the early eighteenth century, English-speaking escaped Akan slaves were at the forefront of the Maroon fighting against the British. Cudjoe led the Leeward Maroons in western Jamaica, while Quao and Queen Nanny were the leaders of the Windward Maroons in the Blue Mountains of eastern Jamaica. The rebellion finally ended, however, with the signing of peace agreements in 1739 and 1740.
Jamaica's pirate economy
Spanish resistance continued for some years after the English conquest, in some cases with the help of the Jamaican Maroons, but Spain never succeeded in retaking the island. The English established their main coastal town at Port Royal.
Under early English rule, Jamaica became a haven of privateers, buccaneers, and occasionally outright pirates: Christopher Myngs, Edward Mansvelt, and most famously, Henry Morgan.
In addition to being unable to retake their land, Spain was no longer able to provide their colonies in the New World with manufactured goods on a regular basis. The progressive irregularity of annual Spanish fleets, combined with an increasing desperation by colonies for manufactured goods, allowed Port Royal to flourish and by 1659, two hundred houses, shops, and warehouses surrounded the fort. Merchants and privateers worked together in what is now referred to as "forced trade." Merchants would sponsor trading endeavors with the Spanish while sponsoring privateers to attack Spanish ships and rob Spanish coastal towns. While the merchants most certainly had the upper hand, the privateers were an integral part of the operation. Nuala Zahedieh, a lecturer at the University of Edinburgh, wrote, "Both opponents and advocates of so-called ‘forced trade’ declared the town’s fortune had the dubious distinction of being founded entirely on the servicing of the privateers’ needs and highly lucrative trade in prize commodities." She added, "A report that the 300 men who accompanied Henry Morgan to Portobello in 1668 returned to the town with a prize to spend of at least £60 each (two or three times the usual annual plantation wage) leaves little doubt that they were right.”
The forced trade became almost a way of life in Port Royal. Michael Pawson and David Busseret wrote "...one way or the other nearly all the propertied inhabitants of Port Royal seem to have an interest in privateering." Forced trade was rapidly making Port Royal one of the wealthiest communities in the English territories of North America, far surpassing any profit made from the production of sugarcane. Zahedieh wrote, "The Portobello raid [in 1668] alone produced plunder worth £75,000, more than seven times the annual value of the island’s sugar exports, which at Port Royal prices did not exceed £10,000 at this time."
An illustration of pre-1692 Port Royal
Henry Morgan, governor of Jamaica
English map of Jamaica from the 1670s
European colonies in the Caribbean during the 18th century
1692 earthquake and the collapse of Port Royal
On 7 June 1692, a violent earthquake struck Port Royal. Two-thirds of the town sank into the sea immediately after the main shock. According to Robert Renny in his 'An History of Jamaica' (1807): "All the wharves sunk at once, and in the space of two minutes, nine-tenths of the city were covered with water, which was raised to such a height, that it entered the uppermost rooms of the few houses which were left standing. The tops of the highest houses, were visible in the water, and surrounded by the masts of vessels, which had been sunk along with them." Before the earthquake, the town consisted of 6,500 inhabitants living in about 2,000 buildings, many constructed of brick and with more than one storey, and all built on loose sand. During the shaking, the sand liquefied and the buildings, along with their occupants, appeared to flow into the sea.
In the immediate aftermath of the earthquake, it was common to ascribe the destruction to divine retribution on the people of Port Royal for their sinful ways. Members of the Jamaica Council declared: "We are become by this an instance of God Almighty's severe judgement."  This view of the disaster was not confined to Jamaica; in Boston, the Reverend Cotton Mather said in a letter to his uncle: "Behold, an accident speaking to all our English America." After the earthquake, the town was partially rebuilt. But the colonial government was relocated to Spanish Town, which had been the capital under Spanish rule. Port Royal was devastated by a fire in 1703 and a hurricane in 1722. Most of the sea trade moved to Kingston. By the late 18th century, Port Royal was largely abandoned.