Carla Gardina Pestana, The English Conquest of Jamaica: Oliver Cromwell’s Bid for Empire (Cambridge: The Belknap Press of Harvard University Press, 2017).
It is an exciting time to be a scholar of Caribbean history. From conferences to publications, the past decade has seen historians of early America, Latin America, and the Atlantic world turn to the Caribbean for insights into the development of empire, slavery, race, and commerce. In this resurgence of Caribbean historiography, the seventeenth century has emerged as a pivotal period. That said, by taking a relatively well-known event like the Western Design, UCLA Professor and Joyce Appleby Endowed Chair of America and the World, Carla Gardina Pestana, demonstrates the value of exploring the early Caribbean in her new book The English Conquest of Jamaica: Oliver Cromwell’s Bid for Empire. Pestana’s work aptly shows the profound intellectual pay-off for historians willing to explore the seventeenth-century Caribbean with bigger questions about imperialism, race, religion, and gender.
The accepted narrative about the Western Design and the English conquest of Jamaica goes something like this: Oliver Cromwell, flush with success in Ireland, dispatched a massive amphibious fleet in late 1654 to strike at the heart of Spanish America. The commanders of that fleet, Robert Venables and William Penn, decided to attack the Caribbean island of Hispaniola first in order to use it as a base to conquer the rest of Spain’s American empire. However, the Spanish defeated the English at Hispaniola and a significant portion of the invaders died of disease or enemy lances. The commanders, fearful of returning to London with nothing to show for their efforts, decided to take the lightly populated island of Jamaica instead. And, while the invasion there proved successful, the English colony struggled to take root until the Restoration of the Stuart monarchy brought administrative oversight to the island in the form of trade regulations and royal governors. From there, Jamaica transformed seemingly overnight into a sugar-producing monstrosity that consumed the labor and lives of enslaved Africans for the profit of absentee planters in England.
Perhaps because this narrative is so often repeated in scholarship more concerned with the eighteenth-century history of Jamaica, the last full-length monograph about the Western Design was S. A G. Taylor’s 1965 classic, The Western Design: An Account of Cromwell’s Expedition to the Caribbean. However, Pestana has recently given us reason to linger over the early history of English Jamaica. She argues that, “because its seizure was deemed a consolation prize,” the invasion of English Jamaica “has not been appreciated as the innovation that it in fact represented” (256). This is especially problematic as many of the imperial advances commonly associated with the Restoration monarchy actually started under Cromwell and involved the invasion of Jamaica. First, the Western Design innovated the use of state finance for naval operations that presaged the rise of British maritime dominance in the eighteenth century. Second, the invasion of the West Indies changed the relationship between London and the colonies, as imperial administrators conceived of the colonies as a single entity for the first time and sought to organize imperial governance over those territories to maximize revenue potential. In other words, rather than a false start, Cromwell’s Western Design and the subsequent conquest of Jamaica “formed a template for England’s and later Britain’s imperial future” (248).
Organized into nine chronological chapters, The English Conquest of Jamaica traces the Western Design from the planning stages through to the post-Restoration settlement of Jamaica by English planters. According to Pestana, the planning of the Western Design signaled the beginning of an imperial relationship in which officials in London conceived of the colonies as “a unit rather than independent entities” (12). This translated to an expectation between Cromwell and his advisors that the colonies would lend men and supplies to the fleet. However, as Pestana explains, “West Indian realities complicated recruitment,” in ways unanticipated in London (52). Namely, Venables and Penn confronted the dual issues of debt and labor obligations as they sought to carry men off of the Leeward Islands for the invasion of Hispaniola. Men who owed money or labor to others could not legally leave the island and the commanders of the Western Design confronted obstinate local officials who tried to prevent servants or debtors from joining the Design.
As the largest amphibious fleet launched by the English to date, there are many theories as to why the invasion of Hispaniola failed so spectacularly. Some attribute it to the tropical disease environment or the mismanagement of the forces, but Pestana argues that it was the size of the invasion force that likely led to its defeat. Through a careful analysis of the kinds of deadly diseases confronted by Europeans in the Caribbean in the mid-seventeenth century, she asserts that, “Bad diet and poor water quality seem the most likely causes of the high rate of illness among the troops” (89). This claim supports her overall intervention that a smaller, more mobile force, like that of Francis Drake who sacked the capital city of Hispaniola nearly a century earlier, would have been capable of seizing the Spanish island. As it was, Venables and Penn lacked the food, water, weapons, and ammunition to equip such a large force that, because of its size, moved slowly. Rather than a rapid attack supported from sea, the English forces spent too much time bogged down miles from Santo Domingo, consuming supplies and dying of dehydration. As Pestana explains, the invasion of Hispaniola “arguably neither required nor benefitted from a massive but relatively ill-supplied force” (92).
The failure to secure Hispaniola proved more than embarrassing for Cromwell, as Pestana explains. After all, Cromwell’s ascension to power depended upon his ability to claim that his actions received divine sanction – an argument that proved more difficult to maintain after an overwhelming defeat. According to Pestana, “This failure moved England a step closer to the demise of its revolution” and Cromwell’s critics used it to attack the providentialism that undergirded the Commonwealth (93). And, almost as quickly as Penn and Venables gathered their shattered force for an attack on Spanish Jamaica, the engines of propaganda began to produce promotional literature that extolled the superiority of that smaller island as a prize. Despite the fact that during the years following the invasion, “the army was barely functioning and the displaced population had not been subdued,” Pestana explores the construction of “the party line” that Jamaica was preferable to Hispaniola (139, 141). Perhaps it should not be surprising that the promotional literature neglected any discussion of the island’s previous residents especially since the English were still fighting the Spanish and populations of African descent for control over the island.
The second half of The English Conquest of Jamaica turns to the five years of guerilla warfare, death, and struggle that preceded the full settlement of the island by English planters. It is here that Pestana’s work contributes to a historiography that too often treats the conquest period as a prelude to eighteenth-century Jamaica. Perhaps most impressive, Pestana skillfully teases out a coherent narrative from a complex situation on the island. As she argues, the English in Jamaica were actually engaged in two wars beginning in 1655, one against a Spanish resistance and one against independent African enclaves. This point serves as a powerful corrective to the tendency to portray the war for Jamaica ending with the expulsion of the Spanish and the subsequent conflict on the island as a campaign to destroy the remaining maroon settlements. According to Pestana, “Equating these refugees with later runaway slaves who created similarly independent communities in the mountains domesticates African resistance” (184). Through a careful analysis of who fought who, when, and where in Jamaica, Pestana complicates a simplistic conquest narrative, thereby creating space for understanding the role of people of African descent in the fight for control over Jamaica.
In her concluding chapters, Pestana maintains this delicate balance between complexity and effective narrative. Much as the fight over Jamaica proved two-fold in the 1650s, the settlement of the island also proceeded as a two-part process. Pestana explores not just how the English forces first had to conquer Jamaica from the remaining resistance, but also how successful settlement depended on disbanding the army. As she argues, this process “affirms Karen Ordahl Kupperman’s observation that successful colonies required civil institutions” (215). Jamaica flourished as an English colony only when it ceased being a garrison outpost. And, while that point might seem self-evident, The English Conquest of Jamaica explains for the first time how difficult and contested that process was on the island.
This book speaks to a gap in the historiography of Jamaica and one that is surprising considering the available source material about the Western Design and the invasion of the island. Building on historians like James Robertson, Pestana argues that part of our impartial knowledge about this period stems from the efforts of the second generation of Jamaican residents to obscure the island’s origins. According to Pestana, “The difficulty of Jamaica’s beginnings, combined with the defeat on Hispaniola and the later hostility to the Cromwellian Protectorate, meant that Jamaica’s origins were better forgotten” (252). In other words, Jamaican chroniclers from the 1670s forward constructed a narrative of the island that elided the years of struggle over the island precisely to obscure the island’s ties to a regime that committed regicide. Through a careful reading of the sources that survived the transition from Commonwealth to Restoration monarchy, Pestana provides a fluid, impressive book that will doubtless become standard reading for Atlanticists and early Americanists in the years to come.
 For a great bibliography on recent developments in Caribbean history, see Jesse Cromwell, “More than Slaves and Sugar: Recent Historiography of the Trans-imperial Caribbean and Its Sinew Populations,” History Compass 12, no. 10 (October 2014): 770-83.