In May of 1655, under a plan aimed against Spain known as the “Western Design”, the English Fleet of 38 ships and about 8,000 men sailed into Kingston Harbor. The “Roundheads” under Oliver Cromwell’s leadership had many motives for attacking the Spanish. Chief among them was to avenge the deportation of English Settlers from St. Kitts in 1629 and the countless attacks on English ships resulting in the murder and enslavement of their crews. The Expedition assembled to enforce the “Western Design” was perhaps the worst equipped and poorly organized to ever leave England. Sailing in secrecy from Portsmouth England at the end of December 1654, the Expedition achieved some moderate success when, after five weeks at sea, they stopped in Barbados. There eleven Dutch ships were seized by Admiral Penn to be used as transports. Food and arms were demanded along with 4,000 men recruited for the Expedition Army.

Santo Domingo, capital city of Hispanola and a Spanish stronghold was the next target according to the instructions set down in the “Western Design” plan. A tactical error in landing the forces 30 miles outside the city without sufficient food or water caused panic and disorder. Sickness from drinking polluted water and the long march made the Expedition vulnerable to Spanish lancers and local cattle hunters. A complete massacre of the nearly 12,000 man Expeditionary force was only averted by successfully landing a party of sailors who covered their retreat. Nearly 4,000 men were left behind as dead or missing. Fearful of Cromwell’s anger over the failure at Santo Domingo, a hasty decision was made to attack another thinly populated and weakly defended Spanish island; Jamaica.

With less than 1,500 Spaniards on the island and only about 500 able to bear arms, the English made another blunder. Instead of pressing the attack and taking advantage of the superiority of sheer number of troops, they handed the Spaniards an offer to surrender with terms to leave the island if they so desired. Venables, the Expedition leader, unwisely gave the Spaniards time to consider these terms. During this time the Spanish turned their cattle loose and escaped to the North Coast and from there to Cuba. When the Expeditionary army marched into Spanish Town, they found it empty and bare of booty. In anger and disappointment, they destroyed much of the town.

Before departing, the Spanish also freed their slaves and left them behind in the mountains to harry the English until they could amass a force for reconquest of Jamaica. These freed slaves, later to become famous as the Maroons, were organized into a fighting force by Christoval Arnaldo de Ysasi before he too escaped to Cuba. These first Maroons settled mainly in the St. John district of St. Catherine still called Juan de Bolas after one of their chiefs whose real name was Juan Lubolo, on Vera-mahollis Savanna (Los Vermejales) and on the Rio Juana (exact location uncertain). The name “Maroon” probably derived from the Spanish “cimarron” meaning wild, untamed. The Maroons whose number kept swelling from the addition of more runaway slaves continued to raid the English plantations and become a thorn in England’s plan to colonize Jamaica but it was tolerated until 1663 when an offer was made for land and full freedom to any Maroon who surrendered. The Maroons ignored the offer. This failure to come to terms was to result in 76 years of irregular warfare; expenditure of nearly 250,000 English Pounds and passing of some 44 Acts of the Assembly.

Spanish to English Occupation