English in the Colonies


Henry Morgan and his buccaneers used nuns and monks as human shields in their attack on Porto Bello, Panama during July of 1668.

The English Civil War brought the Parliamentarians to power under the Protectorate of Oliver Cromwell. The Anglo-Spanish War (1654 to 1660) broke out when the Spanish captured Fort de Rocher in 1654 with 700 soldiers and a battery of artillery. The Spanish breached the fortification walls with their artillery. The pirates agreed to surrender and opened the gates to the Spanish, who stormed into the fort and butchered most of the 330 pirates along with the townspeople.

Oliver Cromwell saw the attack and massacre by the Spanish at Fort de Rocher against the mostly English pirates as an attack on England and as an opportunity to gain one of Spain’s most lucrative colonies. Cromwell ordered a fleet of 34 ships, 6,000 soldiers, and 7,000 marines and pirates to put Santo Domingo under siege and to claim Hispaniola as an English colony in 1655. This expedition was part of Cromwell’s grandiose plan to dominate the Caribbean and to employ English privateers to capture Spanish treasure ships.

More than 13,000 English soldiers, marines, and pirates landed 30 miles from the city of Santo Domingo and marched through the jungle to attack the city from its landward side. After four days of marching, the English army was ambushed by 2,400 Spanish soldiers, militia, and vaquero cavalry armed with lances. Discipline in Cromwell’s New Model Army broke down as 3,000 English troops in the vanguard were cut down in a crossfire of musket balls and grapeshot followed by charges by the vaquero cavalry, who rode down and impaled the fleeing Englishmen on their lances.

After the English force was reembarked onto the ships, the fleet failed to subdue the Spanish fortifications through bombardment and left to evict the Spanish from Jamaica instead. The naval commander, William Penn, took over command of the entire operation from Robert Venables after the disaster at Santo Domingo.

On the way to Jamaica, 1,500 English troops died from malaria and 1,500 more troops were drowned when four ships went down in a storm. Jamaica had only 1,500 Spanish settlers and no fortifications. Around 600 Spanish militiamen were routed by the 7,000 English soldiers and pirates that had descended on Jamaica.

In 1655, Port Royal became the new English pirate base, with a harbor that could hold 500 ships. The English established a licensing office in Port Royal, where ship owners could get a privateering license to conduct their depredations against the Spanish with the government’s approval. By the late 1600s, there were thousands of pirates based at Port Royal, which meant they had the numbers to launch major attacks throughout the Caribbean basin.

In 1660, England’s war with Spain ended, and King Charles II was restored as King of England after the death of Cromwell. Sir John Modyford was appointed governor of Jamaica with orders to halt the pirate attacks against the Spanish. Modyford, who regularly received a cut of the captured Spanish treasure, found excuses to allow the pirates to continue raiding Spanish ships and settlements. King Charles sent a number of letters to Modyford ordering him to force all of the pirates back to port. Modyford sent letters back to King Charles in which he claimed that the pirates in Jamaica had stopped their attacks, but in truth he continued to approve expeditions against the Spanish because he couldn’t control the pirates.

Modyford dispatched Henry Morgan in 1667 to lead his first major pirate expedition against the Spanish. The Welsh pirate took a force of 700 buccaneers and 12 ships and attacked Puerto del Principe, Cuba, where he captured 500 Spanish hostages. The residents of Puerto del Principe were tipped off by a prisoner, who had escaped when Morgan landed in southern Cuba to recruit 200 French pirates with two ships to join his expedition.

When Morgan’s force reached Puerto de Principe, it marched toward the city through thick jungle that bypassed a Spanish ambush on the main trail. Once the pirates reached the city, they found close to 1,000 Spanish militiamen in battle formation. The pirates fought a four-hour battle with the militia. The buccaneers’ superior marksmanship and discipline eventually routed the Spanish militia.

While the battle was raging, most of the inhabitants hid with their valuables in the interior. A few inhabitants were caught and divulged the whereabouts of others who were hiding and the location of various valuables, but only 50,000 pieces of eight were gathered. This amount didn’t come close to paying off the debts for the expedition, so the buccaneers decided that they would attack Porto Bello, Panama, which was considered the Spanish center of trade in the New World. The French abandoned the expedition when one of their men was murdered during an argument with an English pirate.

When Morgan’s force came across a canoe carrying six emaciated buccaneers who had escaped from a Porto Bello dungeon, he swore vengeance. The pirate fleet anchored at Boca del Toro, and Morgan and 500 of his men transferred to 23 large canoes in which they planned to sneak up on Porto Bello in a night attack. Once they landed, the pirates broke into a blockhouse manned by five soldiers. The buccaneers made the mistake of calling out for the men to surrender or be cut down. The Spaniards opened fire and shot a couple of pirates before they were rushed and run through by swords. The firing alerted the other Spanish fortifications that an attack was under way.

The pirates quickly charged across the beach past the walls of Santiago Castle and into Porto Bello and started killing every person they could find. After securing Porto Bello, the pirates charged through the shallow surf to take the half-completed Geronimo Castle, whose five defenders surrendered after taking only a few badly aimed shots. At that point, the pirates turned back toward Santiago Castle using captured priests and nuns as human shields. The fighting was desperate with swords, firelock pistols, and cutlasses until the entire Spanish garrison lay dead.

Morgan lost 18 dead and 34 wounded in the battle for Santiago Castle. San Felipe Castle subsequently surrendered after they had repulsed a pirate assault. The Spanish sent a militia force of 800 men from Panama City to attack Morgan’s men, but the militia was no match for the violent pirates, who made short work of this force and sent them back in defeat.

Morgan’s men terrorized the people of Porto Bello until they had gathered 250,000 pieces of eight ($12.5 million in today’s money). Each man received an equivalent of $12,000 as his share. Morgan returned to Port Royal with evidence in a letter written by the Spanish governor of his government’s intention to invade Jamaica.


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