The Western Design: An Account of Cromwell’s Expedition to the Caribbean

Taylor, S. A. G., The Western Design: An Account of Cromwell’s Expedition to the Caribbean, Kingston: Institute of Jamaica and the Jamaica Historical Society, 1965.

The Anglo–Spanish War was a conflict between the English Protectorate under Oliver Cromwell and Spain, between 1654 and 1660. It was caused by commercial rivalry. Each side attacked the other's commercial and colonial interests in various ways such as privateering and naval expeditions. In 1655, an English amphibious expedition invaded Spanish territory in the Caribbean. The major land actions took place in the Spanish Netherlands. In 1657, England formed an alliance with France, merging the Anglo–Spanish war with the larger Franco–Spanish War.

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Jamaica was the casus belli that resulted in the actual Anglo-Spanish War in 1655.[5] Weakened by fever, the English force then sailed west for the Colony of Santiago (present day Jamaica), the only Spanish West Indies island that did not have new defensive works. They landed in May 1655 at a place called Santiago de la Vega, now Spanish Town. They came, and they stayed, in the face of prolonged local resistance that was reinforced by troops sent from Spain and New Spain (México). In 1657 the English Governor invited the Buccaneers to base themselves at Port Royal on Santiago, to deter the Spanish from recapturing the island. For England, Jamaica was to be the 'dagger pointed at the heart of the Spanish Empire,' although in fact it was a possession of little value then.[4] Cromwell, despite all difficulties, was determined that the presence should remain, sending reinforcements and supplies. New Spanish troops sailing from Cuba, lost the Battle of Ocho Rios in 1657 and the Battle of Rio Nuevo in 1658, failing in their attempts to retake Jamaica.