Control of Jamaica established an English presence in the Caribbean from which English privateers and pirates could attack Spanish shipping and colonies; additionally, the English developed a plantation system based on African slave labor. Formal control was ceded fifteen years after the initial attack via the Treaty of Madrid, July 8, 1670.
The attack on and conquest of Jamaica were part of the Western Design, developed by England’s lord protector Oliver Cromwell,
The Spanish opposition to the English attempt to plant a colony at Providence Island and Spanish cruelty toward Native Americans convinced Cromwell that peaceful relations between England and Spain were not possible. Opposition to the Western Design was raised in England by those who felt the plan was too ambitious, while others advocated attacking mainland South America near the Orinoco River. Many New England colonists feared the dangers of tropical heat and disease. Planters on Barbados worried that such an attack would ruin England’s reputation with Native Americans and slaves and hurt commerce.
The proposal was discussed in the Council of State in June, 1654, and in August, 1654, England demanded freedom of religion and the official right for free trade for English in Spanish territories, although there was already much “unofficial” trade. On August 18, 1654, instructions were issued to the co-commanders, General at Sea Sir William Penn
In December, 1654, about forty ships with three thousand troops sailed from Portsmouth, England, and when they reached Barbados, an additional five thousand raw recruits were added, in February, 1655. The ships’ crews were placed on reduced rations, and Penn and Venables were squabbling. The fleet’s instructions designated the main target to be either Hispaniola or Puerto Rico, with Cuba as a secondary objective. In mid-April, 1655, the fleet attempted to land on Hispaniola, but the rocky coastline posed a problem. They eventually landed about 30 miles (48 kilometers) from Santo Domingo, the island’s major settlement. Sickness and a tough march to the settlement were major factors in the English defeat on April 17, 1655; after being routed again on April 25, 1655, the English withdrew. They had lost four thousand men.
The expedition then sailed to Jamaica, hoping to find something to show for its efforts. Spanish fisherman alerted authorities to the approaching English fleet, which anchored at what is now Kingston Harbor. The Spanish, recognizing that they had no way to defend against such superior forces, evacuated with their possessions. Penn led an assault with the ship Martin to probe the defenses of the harbor’s fortress, and then the Martin was beached near the fortress and English troops landed without resistance on May 10, 1655. However, they lost an important advantage when they did not pursue the fleeing Spanish troops to the settlement of Santiago de la Vega.
In the following days, the English gained control of key settlements, but disease, lack of provisions, and extremely poor morale caused the English to fare poorly against the Spanish and Maroons, former slaves, who waged guerrilla warfare against them. Lack of a supporting fleet helped account for the significant toll among the English troops—about half of them were dead by December, 1655. Already, on June 25, 1655, Penn and his portion of the fleet had sailed back to England, and Venables and his ships returned shortly after that. Since neither commander had received orders to return, they were technically guilty of desertion.
Penn and Venables were jailed for their unauthorized return, and Cromwell was livid over the failure of the expedition to achieve its primary objectives. Especially galling was Penn’s failure to attack the Spanish treasure fleet, which had arrived in Havana, Cuba, three weeks after he had left. Penn had received word of its arrival while at sea, but he decided against returning to the Caribbean to engage it. Venables wrote an account of the voyage in which he laid blame for the failure on poor organization, the officers, and the quality of the men, but his strongest accusation was against Penn for landing so far from Santo Domingo. Historians agree that the biggest factor in the expedition’s failure was the divided command and animosity between Penn and Venables. Other factors that contributed to the expedition’s failure were lack of accurate information about Spanish possessions in the Caribbean and logistical problems of operating at such a great distance from England.
Spanish reaction was initially relatively mild—an embargo was placed on English trade, and English merchants and goods in Spanish ports were seized. Privateers from the Spanish Netherlands were launched against English shipping, and Spain formally declared war on England in March, 1656. The English decided against any additional large-scale expeditions and focused attention on attempting to hold on to Jamaica, encouraging English colonists to settle there, and seeking to capture the Spanish treasure fleets. Spanish guerrilla activity largely ceased after April, 1660, when Jamaica’s last Spanish governor, Don Christoval Arnaldo y Ysassi
The failure of the Western Design was Oliver Cromwell’s greatest disaster, causing him to rethink whether the operation had God’s blessing. Tremendous money went into the planning and provisioning of the expedition, and serious financial consequences resulted from the expedition’s inability to capture the treasure fleet in order to “pay for itself.” The immediate consequence was that, contrary to Cromwell’s assumptions, the assault led to war with Spain in Europe. Cromwell had hoped that attacks in the New World would be tolerated without wider consequences in the Old World. Although conditions on Jamaica were extremely rough and difficult and the English government lamented the fact that few settlers migrated to Jamaica, the colony gradually stabilized and increased the English presence in the Caribbean, becoming an important part of the growing British Empire.
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Baumber, Michael. General-At-Sea: Robert Blake and the Seventeenth-Century Revolution in Naval Warfare. London: John Murray, 1989. Part 4 is valuable for understanding the naval war between England and Spain that resulted from the Western Design and the English capture of Jamaica. -
Capp, Bernard. Cromwell’s Navy: The Fleet and the English Revolution, 1648-1660. Oxford, England: Clarendon Press, 1989. Places the Western Design and the capture of Jamaica within the broader context of Cromwell’s use of the navy for military and foreign policy purposes. -
Gardiner, S. R. 1655-1656. Vol. 4 in History of the Commonwealth and Protectorate. London: Longmans, Green, 1903. Reprint. Gloucestershire, England: Windrush Press, 1989. Although over a century old, this classic work’s treatment of the attack in chapters 45 and 48 is still extremely valuable. -
Kupperman, Karen Ordahl. “Errand to the Indies: Puritan Colonization from Providence Island Through the Western Design.” William and Mary Quarterly, 3d ser. 45 (1988): 70-99. This article focuses on the religious motivations behind English Puritan attempts to establish a “godly” settlement in the Caribbean area. -
Pincus, Steven C. Protestantism and Patriotism: Ideologies and the Making of English Foreign Policy, 1650-1668. New York: Cambridge University Press, 1996. This work analyzes the impact that religious views and public opinion had on the formation and execution of English foreign policy. -
Venning, Timothy. Cromwellian Foreign Policy. New York: St. Martin’s Press, 1995. Chapter 5, “The Western Design,” analyzes why Cromwell exercised less caution in the attack on the Spanish in the Caribbean compared with his handling of international relations with France.
Oliver Cromwell; Philip IV.