Cromwell's “Western Design”—the Protectorate's military effort to challenge Spanish hegemony in America—is typically narrated as a tale of poor planning, humiliating defeat, and catastrophic loss of life. Carla Pestana challenges this careworn account of imperial opportunities lost. Using sources that have been “overlooked or used without regard” for “context” or “origin” she painstakingly reconstructs the activities of the English navy and army, following them from Barbados to Hispaniola to Jamaica (2). Pestana deftly melds military, religious, and cultural histories, producing a fresh interpretation of the “monumental nature” of the Western Design which resulted in England's seizure of Jamaica in 1655 (12). Pestana portrays the Cromwellian scheme as the denouement of a revolutionary moment—one that reshaped the English state and permanently altered the power dynamics between England and Spain. She also unsettles longstanding assumptions about the most significant events and the most important players in the history of colonial Jamaica. Engaging in more than a decade of imperial conflict, the Western Design's hard-bitten leaders and motely group of soldiers bear little resemblance to the more familiar pirates, merchants, and planters who take pride of place in conventional accounts of the West Indies. Religiously inspired and more often just struggling to survive, they had motives that diverged sharply from the “profit maximization” impetus that is traditionally cited as driving England's involvement in the region (154).

Following a roughly chronological timeline, Pestana alternates between chapters that detail English military activities in the Caribbean and those that analyze literary representations of the events. Although secrecy shrouded the Western Design, its scale raised European expectations of another Cromwellian success before the venture was launched. But, as the men who set sail for the Caribbean learn, the best laid plans of mice and men go awry. Chapter 2 exposes the disjuncture between metropolitan plans and “colonial conditions,” a theme that Pestana returns to throughout the book (53). When Cromwell's men reach Barbados, they encounter resentment rather than the subservience they expect. After struggling to enlarge their troops with local recruits and failing to acquire necessary firearms and food supplies, the military sets out for Hispaniola where the divergence between imperial strategy and local circumstances intensifies. Chapter 3 follows the footsteps of an ill-equipped and poorly provisioned army as it embarks on a long march in the tropics without adequate water or food. Thousands of men died of starvation, dehydration, and disease (88). With chapter 4, Pestana returns to Europe, exploring the religious dimensions of English and the Spanish interpretations of the event in print culture.

The reader does not learn about Jamaica—the place in the book's title—until chapter 5. It is in the second half of the book that Pestana makes her most important contributions. She challenges a historiography that treats Jamaica as predestined to become dependent upon plantations worked by enslaved Africans. Instead, the period of English military occupation of the island points toward a different trajectory. Contesting the seminal work of Richard Dunn, Pestana argues that the first generation of soldier-settlers had no interest using Barbados as a blueprint for Jamaica. The march toward sugar and slave labor was not inevitable. Instead, early English settlers followed Spanish precedent, practicing mixed agriculture and rearing livestock. They lacked the resources to purchase enslaved Africans and displayed little interest in doing so. However, people of African descent feature prominently in Pestana's work, though not in their standard roles as slaves or maroons. She takes issue with characterizations of varied groups of African-descended peoples as “maroons,” arguing that this misnomer downplays their significance to both the English invasion and the “international rivalries” (184). Instead, Pestana emphasizes the importance of ladinos—a Spanish term for the African-descended people who were born on the island and spoke Spanish (146–47)—who fought against the English and also forged alliances with them (208). Pestana implicitly identifies these people as the most adaptable and successful of Jamaica's settlers and views instances of peaceful alliances and the creation of mixed-race communities as offering “a different path for relations between English and Africans” (246).

The English Conquest insists upon the innovative nature of the Western Design and stresses its importance in forging a nascent English empire. As Pestana states, the Western Design “brought England to the centre of the Caribbean sea,” forcing Spain to accept the presence of its rival (185; 213). Though it was not an immediate success, the Western Design inalterably shifted power relations between European empires in the Americas. These bold assertions prime the reader for a strong account of how Cromwell's plans directly transformed England's position in the world. Yet by ending the book in the 1680s, Pestana leaves these expectations somewhat unfulfilled. Most of her work details the failures, rather than the strengths, of the English state overseas. On a similar note, she foreshadows Jamaica's centrality to the empire without offering strong evidence of the colony's significance. The book provides a more historically grounded and gritty blow-by-blow account of a new brand of military colonialism launched by Cromwell in the mid-seventeenth century, one that discloses England's weaknesses as much as its strengths on the international stage during this time.