Though England had established settlements in the Caribbean for decades, Oliver Cromwell's ambition to conquer Spain's “hub of empire” and establish a larger English presence in the West Indies signaled an entirely new development in the country's history. Both republican and imperial, the so-called Western Design represented the first large-scale English invasion of the Americas, utilized a navy rather than privately financed ships to enter these faraway waters, and permanently altered the country's geopolitical and commercial interactions with the world. Yet in the end, the Western Design was a failure, with only Jamaica seized as a consolation prize, and a not very enticing one at that. But what about that island?

The English Conquest of Jamaica is a much-needed addition to the historiography of the English Atlantic world and the ongoing debate around the origins of the British Empire. Relying on an exhaustive use of primary sources, Carla Gardina Pestana provides a narrative and analytical history not only of Jamaica's conquest and settlement, but also of the previous failed English attempt to take Hispaniola. Pestana seeks to disrupt the assertion, established most famously by Richard Dunn, that described the Western Design as a “provisional” episode in empire history, “mired” in “freebooters” and “plunder” (13); while Cromwell “failed to conquer Spanish America,” she writes, “that fact should not obscure what his Design did accomplish” (14).

The problem is that none of the “enhanced state power” and “imperial vision” (48, 26) that she discusses in the introduction ever came to fruition in 1650s Jamaica, which raises the question as to whether this was the beginning of an “empire,” when none of it quite worked at the time (and when the word itself was understood differently, as Nicholas Canny has pointed out). England “had more naval resources at its command than ever before” and five commissioners to implement the design (28, 36); but “intricate planning had not foreseen colonial conditions” (53), as “colonies were as unprepared for the fleet as the fleet was for … the colonies” (56). Recruits, especially from already settled islands such as Barbados, proved to be difficult, while weapons were in short supply to the point where pikes had to be fashioned from cabbage palmettos. The attempt to take Hispaniola, beginning in April 1655, proved disastrous, with the fleet unable to land at an appointed location, and the army sinking into demoralization and cowardice. The resulting failure was “shattering,” requiring the “work of interpreting the fiasco,” especially when the favorable providence that had sustained the English so far took a decidedly downward turn (89, 94).

Next up was the “less-desirable” yet already well-settled Jamaica, where the English sought “not to pillage but to plant” (122). Pestana is particularly good in describing the hellish conditions of disease and starvation that belied the rosy-scenario letters and treatises that described the island as a “fantasy of plenty” (142). Importantly, the English were not interested in “making Jamaica into a bigger Barbados,” and, specifically, cultivating the slave-labor commodity—sugar—that would ultimately save the colony in the future (149, 153). But rather than reflecting any kind of administrative efficacy or state planning, provisions from home were scant, the supply chain “moved haltingly,” new settlers were sparse in coming, the troops ordered to stay and plant were disgruntled, the colony remained a militarized territory, and resistance continued to shadow the English in the form of Spanish guerillas or former slaves (165, 182).

In the end, any semblance of civil government or success would not be achieved until 1665, and while Charles II retained previous officers and planners (who conveniently professed a royalism all along), this did not mean that the Cromwellian settling of Jamaica in any way “led the way.” Pestana does not quite assert this either, for hers is a book that describes an always contingent design that began in failure and only slowly crawled its way out: a design that collapsed and then was redesigned, perhaps, in the wake of new and vastly attenuated realities. In conveying this story, she has written a significant work, even if the book is historiographically undersourced and rarely mentions the scholars of those disputed “traditional narratives” with whom she takes issue. There are also many redundancies that an editor should have noticed and cut. Nevertheless, The English Conquest of Jamaica belongs with the work of Karen Kupperman, Hilary Beckles, and others, in illuminating the dark origins of a colony that would only become darker in the years to come.