| Invasion of Jamaica | |||||||||
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| Part of theAnglo-Spanish War of 1654–1660 | |||||||||
17th-century map of Jamaica | |||||||||
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| Belligerents | |||||||||
| Commanders and leaders | |||||||||
| Strength | |||||||||
| 1,500 settlers[1] | ||||||||
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An English expeditionary force capturedSpanish Jamaica in May 1655, during theAnglo-Spanish War (1654–1660). It was part of an ambitious plan byOliver Cromwell to undermine or obliterate Spanish dominance in the Americas and to acquire new colonies there, known as theWestern Design.
Although major settlements like Santiago de la Vega, nowSpanish Town, were poorly defended and quickly occupied, resistance by escaped slaves, orJamaican Maroons, continued in the interior. The Western Design was largely a failure, but Jamaica remained in English hands, and was formally ceded by Spain in the1670 Treaty of Madrid. TheColony of Jamaica remained a British possession until independence in 1962.
In 1654,Oliver Cromwell and his Council of State planned a surprise attack onSpanish America. There were a number of reasons for this, including theCommonwealth's weak economic position, and finding an outlet for large numbers of disgruntled veterans from theWars of the Three Kingdoms.[2]
The expedition left England in December 1654, comprising a fleet of 17 warships and 20 transports, carrying 325 cannons, 1,145 seamen, and 1,830 troops (later reinforced by contingents from other English West Indian colonies to 8,000 strong).[3] Command was jointly held by AdmiralWilliam Penn, andRobert Venables, an experienced soldier recently returned from Ireland. The Spanish had been aware of these preparations since July, and ordered improvements to the defences ofHispaniola, correctly assumed to be the main target.[4] The fleet arrived inBarbados at the end of January 1655, and after two months of refitting, sailed for Hispaniola; on 13 April, Penn landed 4,000 men under Venables nearSanto Domingo.[3] Suffering from dysentery, and harassed by black and mixed-race Spaniards on the march,[5]the expedition failed with the loss of 1,000 men.[3] The English troops evacuated on 25 April.[3]
Even before this, relations between Penn and Venables were strained, and the failure at Hispaniola led to a complete breakdown. Although they had broad discretion, Venables sought to salvage the expedition by attacking the poorly defended Jamaica. Penn, however, opposed the plan so strongly that Venables feared the fleet might abandon his troops once ashore.[6]

On 19 May, two Spanish settlers saw Penn's fleet as it rounded Point Morant and warned Governor Juan Ramírez de Arellano; taken by surprise, the Spanish made what few defensive preparations they could. One of the English participants later recorded;
On Wednesday morning, being the 9th of May, we saw Jamaica Iand, very high land afar off. Wednesday the 10th our souldiers in numbers 7000 (the sea regiment being none of them) landed at the 3 forts...[7]
At dawn on 21 May, Penn's fleet enteredCaguaya Bay, which was extremely shallow. As a result, Penn transferred from the 60-gunSwiftsure toMartin, a lighter 12-gun galley, leading a flotilla of smaller craft, although some of these, including theMartin, still briefly grounded. There was an exchange of shots with the Spanish battery covering the inner anchorage, with resistance from a small number of settlers under Francisco de Proenza, a local estate owner, but they soon surrendered.[8]
Penn disembarked the landing force, which quickly occupied Santiago de la Vega, some six miles away. Venables, despite being sick, came ashore on 25 May to dictate terms; the island was annexed by the Commonwealth, and the Spanish inhabitants had to evacuate within a fortnight, on pain of death. After doing what he could to delay the inevitable, Ramírez signed on 27 May; shortly thereafter, he sailed forCampeche, Mexico, but died en route.[9]
Not all the Spanish accepted the English occupation; after evacuating noncombatants from northern Jamaica to Cuba, Proenza established his headquarters at the inland town of Guatibacoa. He allied with theJamaican Maroons based in the mountainous interior, underJuan de Bolas andJuan de Serras, inaugurating a guerrilla war against English occupation.[10]

Penn left for England with half the fleet on 25 June, to ensure his version of why the expedition failed was heard first. He was soon followed by Venables, who arrived in England on 9 September, emaciated and sick; justifying their fears, Cromwell threw them both in theTower of London. Although released soon after, they were removed from command; Penn was rehabilitated after the1660 Restoration, but this ended Venables' career.[6]
The troops left in Jamaica suffered heavily from disease and malnutrition; within a year, only 2,500 remained from the original invasion force of 7,000. Spanish losses were also severe; one of the first victims was de Proenza, who lost his sight, and was succeeded by Cristóbal Arnaldo de Issasi, whose family had been among the original Spanish settlers.[11]
When the English invaded, the Spanish freed their slaves, who fled into the interior, where they established free and independent communities asMaroons. Issasi was appointed governor in place of Ramirez, and, allied with the Maroons, under the leadership of de Bolas and de Serras, tried to frustrate English efforts to establish control over the interior.[12] Spanish attempts to retake Jamaica ended with defeats atOcho Rios in 1657, andRio Nuevo in 1658. After this, English governorEdward D'Oyley persuaded de Bolas to switch sides; without their support, Issasi finally accepted defeat, and fled to Cuba.[13]
Despite continuing their diplomatic efforts to have it returned, Spain eventually ceded theColony of Jamaica and theCayman Islands in the 1670Treaty of Madrid. Under British rule, the island became a hugely profitable possession, producing large quantities of sugar for export.[14]