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, injured badly or possibly killed.
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 Jamaica, 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 English colonisation
Cromwell's Protectorate 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 after the restoration of 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.
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.
In 1687, James II appointed the Duke of Albemarle as Governor, who pursued a policy of excluding the planter oligarchy from state offices. 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.