The Western Design, 1655

The English attack on the Spanish West Indies was intended to secure a base of operations in the Caribbean from which to threaten trade and treasure routes in the Spanish Main, thus weakening Catholic influence in the New World. The Council of State first discussed the plan in June 1654. Cromwell's belief that he could attack Spain in the Caribbean yet avoid a war in Europe was influenced by the faulty advice of Thomas Gage — a renegade Dominican who had once been a missionary in the West Indies and was regarded as an expert on the region. Gage maintained that the Spanish colonies of Hispaniola and Cuba were weakly defended and could easily be seized by a determined force.

A committee headed by Major-General John Disbrowe was appointed to supervise arrangements for the expedition. Rather than send established regiments, it was decided to form five new regiments of foot by drafting troops from around the country, where a reduction of forces was taking place. When insufficient numbers were supplied from the regular army, vacant places were filled by raw recruits. Of around 2,500 infantrymen who sailed from England, only about 1,000 were experienced soldiers. Robert Venables, a veteran of the Irish wars, was appointed general commander of land forces. His complaints regarding the poor condition of the troops he was expected to lead were ignored. The naval force was commanded by General-at-Sea William Penn. Like Venables, Penn was an experienced and competent officer, but neither was given overall command of the expedition, which resulted in friction and mutual hostility between them. This was probably exacerbated by the presence of Venables' domineering wife, who is said to have interfered in his plans and criticised the management of the expedition. Two civilian commissioners, Edward Winslow and Gregory Butler, as well as Daniel Searle, governor of Barbados, were also named as leaders of the expedition. They were expected to supervise colonisation of the captured lands once victory had been achieved.

The fleet of eighteen warships and twenty transport vessels set sail from Portsmouth on Christmas Day 1654 and arrived at Barbados a month later. Between three and four thousand additional troops were raised from volunteers among the indentured servants and freemen in the colonies of Barbados, Montserrat, Nevis and St Kitts to make the numbers of the five original regiments up to 1,000 men each and to form a sixth regiment. The troop numbers looked impressive, but they were untrained and badly disciplined. Furthermore, supplies were running low and the joint commanders Penn and Venables were arguing with one another. Morale among the soldiers sank lower still when the civilian commissioners stipulated that they were not to plunder the Spanish colonies they were about to attack but rather to preserve them intact for subsequent English colonisation.

Hispaniola, 1655

The military objectives of the expedition had not been specified by Cromwell but left to the initiative of the commanders when they arrived in the Caribbean. They jointly agreed to attack Hispaniola (now Haiti and the Dominican Republic), and on 13 April 1655, the English fleet arrived off Santo Domingo, the main Spanish stronghold on the island. General Venables intended to disembark at a point near the mouth of the River Jaina where Sir Francis Drake had landed his troops for his successful raid on Santo Domingo in 1586. However, heavy surf prevented Venables from landing at his preferred site. On 14 April, the English force was landed at the mouth of the River Nizao, twenty-five miles west of Santo Domingo.

The soldiers suffered greatly from heat and drought during the three-day march on the town through difficult tropical terrain. Water bottles had not been provided for the expedition and many soldiers fell ill, including Venables himself who contracted dysentery. The troops reached the outskirts of Santo Domingo on 17 April, but were ambushed while the advance guard reconnoitred the Spanish defences. The ambush almost succeeded in routing the inexperienced English troops and it was only through the discipline of the auxiliary "sea regiment", formed from sailors of the fleet under the command of Vice-Admiral William Goodsonn, that the Spanish were repulsed. Venables ordered a withdrawal from Santo Domingo. He retired to the fleet to be nursed by his wife, which earned the derision of his soldiers, many of whom were also sick but were left ashore with no shelter or supplies.

On 24 April, Venables returned to lead a second assault on Santo Domingo. The following day, Penn's fleet began a bombardment of the town and its outlying defences while Venables' soldiers hauled a mortar through the jungle to attack by land. However, the naval bombardment proved ineffective because the fleet was too far from the shore. The infantry advance ended in failure when the column was caught in another Spanish ambush. Major-General Heane was killed as he tried to rally the wavering troops. Once again, a major disaster was avoided when Goodsonn's naval regiment held firm and drove back the attackers but the infantry refused to make another attack on Santo Domingo. The joint commanders agreed to abandon the attempt on Hispaniola.

The Capture of Jamaica, 1655

Hoping to salvage the situation after the failure of their attack on Hispaniola, Penn and Venables agreed to attempt to capture the neighbouring island of Jamaica, which was a relatively insignificant Spanish provisioning base. It was weakly defended by the Spaniards, so presented an easy target.

The English fleet left Hispaniola on 5 May 1655 and arrived at the anchorage now known as Kingston Harbour on 10 May. The following day, the Martin, a 12-gun galley, was sent close in to the shore defences to provide covering fire while the troops were landed from boats. Heavily outnumbered, the Spanish abandoned their defences without a fight. The English advanced to occupy Santiago de la Vega (later known as Spanish Town), the main Spanish stronghold on Jamaica.

Venables unwisely allowed the Spaniards time to negotiate his terms for surrender. Although they officially surrendered on 17 May 1655, most had taken the opportunity to turn their cattle loose and escape with their most valuable possessions to Cuba, leaving their settlements bare of plunder. The Spaniards also released their slaves and left them behind in the mountains to harass the English until troops for the reconquest of Jamaica could be raised. The freed slaves, later known as "Maroons", were quickly organised into a fighting force. The Spanish had given up all attempts to recapture the island by 1660, but the Maroons continued to raid English plantations and settlements into the 18th century.

Without orders, Penn and Venables left Jamaica soon after its capture. Upon returning separately to England, both officers were charged with deserting their posts. After a brief imprisonment in the Tower of London, they were relieved of their commands. The dispirited English forces left on Jamaica began building Passage Fort, also known as Fort Cromwell, to control access to the harbour. A small community, known as The Point or Point Cagway grew up around the fort.

Penn left Vice-Admiral Goodsonn in command of the naval squadron of twelve ships. Goodsonn led raids on Spanish bases in the Caribbean during the summer of 1655 and spring of 1657. The former Spanish governor of Jamaica, Don Cristobal de Ysassi, attempted to recapture the island with forces from Cuba in the summer of 1657, but the attack was repulsed by acting governor Colonel Edward Doyley. Ysassi returned in May 1657 with thirty companies of foot and succeeded in establishing a fortified position at Rio Nuevo on the northern coast of Jamaica. Doyley marched against Ysassi with 750 of his best troops and decisively defeated the Spaniards at the battle of Rio Nuevo in June 1658. Ysassi fled to Cuba and Doyley was confirmed as the first English governor of Jamaica.

Cromwell urged settlers to go to Jamaica from New England and from other colonies in the Caribbean, but despite the arrival of 1,600 civilian colonists from Nevis in November 1656, the development of Jamaica was slow until after the Restoration when The Point was renamed Port Royal and Fort Cromwell became Fort Charles. Port Royal grew faster than any other town founded by the English in the New World. It became a notorious centre for buccaneering and piracy against the Spanish, even after Spain formally ceded Jamaica to England under the terms of the Treaty of Madrid in 1670.

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