Imperial Designs: Cromwell's Conquest of Jamaica

The Lord Protector’s move on Jamaica transformed Britain’s early empire.

Nautical chart of Hispaniola and Puerto Rico, c.1639.

A massive fleet set sail for Hispaniola in 1654 to conquer the Spanish Caribbean island for the Lord Protector, Oliver Cromwell. Repulsed after three weeks by a much smaller and poorly armed force, the fleet limped away to Jamaica. Botching that conquest as well, the army hunkered down for what would prove a long guerilla war against a small but tenacious remnant of the island’s population. The fleet’s commanders scurried home, where Cromwell threw them in the Tower for abandoning their posts. It was not the Protector’s finest hour.  

This campaign, Cromwell’s ‘Western Design’, has been largely forgotten. A plan of ludicrously audacious ambition, the scheme to dispatch a massive force to conquer the Spanish Americas usually receives a brief dismissal. It has been variously derided as a throwback to Elizabethan Hispanophobia or an expensive and humiliating failure of little permanent consequence. That the Design brought England the island of Jamaica has been deemed a ‘consolation prize’. Although it became a valuable imperial possession in the next century, Jamaica’s status as the site of Britain’s deepest engagement in the enslavement of Africans also retroactively taints that accomplishment. The Protectorate, indeed the entire Interregnum, fits awkwardly into histories of Britain, organised around monarchical reigns. We recall Cromwell favourably as a brilliant general and less approvingly as the mastermind behind the entire Interregnum debacle. We do not remember his role promoting empire or expanding England’s territorial reach. 

The Western Design was nonetheless a pivotal moment in the creation of the British Empire. In its planning and execution, the Design signalled the state’s dawning capacities and emerging aims. In directly confronting Spain in the Americas, Cromwell’s scheme realised a long-standing policy goal and reshaped the international situation. The acquisition of Jamaica transformed British engagement in the world. 

When the Cromwellian state dispatched a massive fleet to the West Indies, it reconfigured the relationship between the state and colonial expansion in three respects. First, the Western Design directly involved the state in seizing lands in the extra-European world. Previously private individuals – whether alone or acting within a chartered company – had managed the work of expansion. With government permission, these delegates planted and managed colonies that operated under the broad but distant authority of the English monarch. With the Design, the government performed the work itself for the first time. Second, the state deployed unprecedented resources. The Protector’s ‘invincible Armada’ rivalled any that had gone to the Americas in the previous century and a half of European engagement. The state gathered men, ships and materials for a massive campaign, all shrouded by a remarkable level of secrecy. The intentionally vague name ‘Western Design’ arose from that concealment; the term replaced a still more opaque ‘Present Design’ after the fleet’s sailing revealed its general destination. Finally, the campaign altered the state’s relationship to distant possessions. Cromwell intended to extract resources from colonies, placing demands in accordance with the government’s expanded expectations as well as its extended reach. When the fleet passed months at Barbados, the islanders confronted novel demands. These new intrusions, innovative at the time, would become routine in the British Empire. 

Besides changing England’s relationship with its imperial possessions, the Design profoundly altered the international situation. In planting a colony, England directly confronted Spain for the first time. The Spanish Habsburgs claimed all of the Americas as their exclusive domain (excepting Portuguese Brazil), but they occupied only territories around the equator. English intrusions had earlier focused on unoccupied areas – either the less attractive lands north of Florida or the tiny islands of the eastern Caribbean. According to Spain, these settlements constituted illegal intrusions; yet, they lacked resources to drive out every interloper. They tacitly ignored those colonies seated beyond the realm of Spanish activity. When an English company earlier planted the shortlived Providence Island colony, Spanish forces attacked it three times before finally eliminating it. In invading the Spanish islands of Hispaniola and Jamaica, the English ignored their usual circumspection. No longer did they heed the prohibition contained in numerous colonial charters against taking lands already occupied by another ‘Christian Prince’.

Their successful occupation of Jamaica shifted the geopolitics of the West Indies. The assault brought wider war with Spain – the first war started in the Americas that shifted to Europe. That war, although its European theatre petered out without official resolution in the late 1650s, continued in the Caribbean until the 1670 Treaty of Madrid. In that agreement, Spain acknowledged not only Jamaica but all England’s American holdings. Responding to the rise in English activity, the French moved in as well. By 1660, they controlled tiny Tortuga, off the coast of Hispaniola; subsequently, France colonised the western end of that larger island, creating what would become St Dominique. 

England’s aggression and the resultant response of other powers changed the nature of conflict in the Caribbean. Hostilities in the region previously pitted various interlopers against Spain, but after 1655 warfare became more complex, with several states fighting each other. The West Indies thereby earned its designation, coined by the historian Eric Williams, as ‘the cockpit of Europe’ – the site where Europe fought its battles. Henceforth, wars in Europe involving any state with possessions in the Americas invariably spilled over into the Caribbean. The Second and Third Anglo-Dutch Wars included a West Indian component, whereas the first war had not. 

The acquisition of Jamaica mattered for the future of empire. Emerging as a valuable possession, it contributed to the massive increase in sugar consumption that would irrevocably transform the European diet. Intensive British engagement in the slave trade followed Jamaica’s conquest. That island first witnessed the trans-shipment of slaves destined for Spanish America and later absorbed numerous enslaved peoples. As the Legacies of British Slave-ownership project has shown, numerous Britons became implicated in the institution, including many who never left Britain. Jamaica was Britain’s premier slave colony when it finally moved to end the trade. 

The Western Design, although remembered, if at all, as a failure, drastically altered England’s engagement in the wider world. It brought the state into the business of colonisation; it saw England directly confront Spain in the process; and it elevated the importance of the Caribbean in European conflicts. Even in failure, the Design taught key lessons about what expansion and empire entailed. As Charles II’s Restoration government built on the accomplishments of the Interregnum, it understood the gains but also the demands that empire generated. 

Carla Gardina Pestana is Professor of History at the University of California, Los Angeles and the author of The English Conquest of Jamaica: Oliver Cromwell’s Bid for Empire (Belknap Press, 2017).