Chapter 5 – Port Royal

View of the Town and Harbour of Port Royal in Jamaica from the Sea

The living conditions of those English forces remaining in Jamaica were harsh. They suffered from a shortage of food and supplies, and their morale was low. Many were ill from dysentery and fevers. Famine threatened. Despite such difficulties, the new masters of Jamaica began consolidating their victory. In the weeks following the conquest, their priority became defence, for they were certain of Spain’s determination to recapture the island.

On the southeast coast of Jamaica, a long sandspit curves south and then west away from the island to form one of the Western Hemisphere’s largest naturally protected deep-water harbours, which is about seven miles long and four miles wide. We know it now as Kingston Harbour. The sandspit—more like a series of low-lying cays covered with Seagrape and palm trees—which is known as Palisadoes, separates the harbour from the Caribbean Sea and acts as a breakwater.

The Spaniards called the cay at the tip of the sandspit Cayo de Carena, and the fort that guarded the approach to their inland capital, Villa de la Vega, they called Caguaya. Later that fort became known as Passage Fort. The first Englishmen to occupy Jamaica mispronounced Caguaya and named the entire area “Cagway.” Apparently, they did not realize the Spaniards used the term to refer only to the fortress. The local English settlers and those who visited regularly called the very end of the long sandspit “the Point.”

Old map of Port Royal | Drawn from The Gentleman’s Magazine 55 (1785)
The light section at the top and going down toward the right is the part of the city lost in the 1692 earthquake; the slightly shaded middle section, the part of the city that was flooded; the darkly shaded bottom section is the part of the city that survived. [Wikipedia.org]

Under Spain’s rule, the Point had been unoccupied, and so was Kingston harbour until 1520 when the Spaniards moved from their capital on the north coast to St. Jago de la Vega. However, the English soon saw the strategic advantage of Cagway as a protection to both the harbour and their renamed capital, Spanish Town.

During these early days, aside from low morale and shortages of almost everything, the invaders had to deal with sudden, unexpected changes in command. In October 1655, Major-General Richard Fortescue, who had succeeded Venables as commander of land forces, died of fever. That same month, Major Robert Sedgwick arrived in Jamaica to take up the post of civil commissioner, superseding Colonel Edward D’Oyley. Cromwell’s original civil commissioner for the Penn-Venables expedition had been Edward Winslow—former governor of England’s Plymouth Colony in North America. However, Winslow had contracted yellow fever and died on 7 May 1655, two days before the fleet reached Jamaica. Shortly after arriving on the island, Sedgwick received a promotion to major-general.

Once Cromwell had dealt with Penn and Venables in London, he seemed to have reconsidered their expedition’s failure to take Hispaniola. He embraced their success in taking the strategically located Jamaica and published a proclamation describing the island as:

… spacious in extent, commodious in its harbours and rivers within itself, healthful by its situation, well stored with horses and other cattle, and generally fit and worthy to be planted and improved to the advantage, honour, and inter-est of this nation.

Cromwell had laws and government orders published and surveyors appointed to layout parcels of land for settlers, who he hoped to attract with an announcement that all “planters and adventurers to that island” would be exempted from paying excise or customs duty “on goods and necessaries transported thither for seven years, and that no customs or other tax or impost would be laid upon any product imported from thence into any other English possession for the next ten years.” 

To begin the process of populating the new colony, Cromwell invited New England colonists, who at that time were facing several difficulties, “to remove themselves or such numbers of them as shall be thought convenient, out of those parts where they now are to Jamaica.” He also promised to resupply General Fortescue’s army and instructed Admiral Goodson that the war must be carried on in the spirit of a crusade. 

Apparently, Thomas Modyford and Thomas Gage, both of whom had gained Cromwell’s ear, convinced the Lord Protector that other Spanish colonies would be easy prey to his forces. Moreover, Jamaica would provide an excellent base from which attacks against Spain’s provinces could be launched. Modyford was a prominent Barbadian planter, of whom we will hear more later. Gage was an Englishman who became a Dominican priest and served several years in Mexico and Guatemala. After returning to England, he publicly abandoned the Roman Catholic Church for a Puritanical form of Anglicanism. Gage served as chaplain and guide to the Penn-Venables expedition that had captured Jamaica. He fell ill and died at Spanish Town in 1656.

Sickness and desertion were depleting the army at an alarming rate. Besides, letters from England—confirmed by statements given by Spanish prisoners—warned that Spain had issued orders for a large fleet to sail from Spain to recapture the island. Jamaica’s commanders, Sedgewick and D’Oyley, took the warnings to heart. In March 1656, they completed the initial construction of Fort Cromwell on the southwest (seaward) side of  the Point (Cayo de Carena).

Fort Cromwell was not very grand then, but it was grand enough to control the narrow entrance to the strategically-critical harbour. Prevailing winds, currents and a narrow channel would force arriving ships to pass within range of the new fort’s guns before entering the harbour. The Spaniards’ main fortress, now called Passage Fort,^[1] was not as well located strategically, for it was on the mainland and could only attack enemy ships once they had already entered the harbour.

^[1]I have read accounts that claim Passage Fort (formerly Caguaya) was another name for Fort Cromwell, but that is not so. Fort Cromwell (named Fort Charles in 1660) was at Port Royal while Passage Fort was at the mouth of the Rio Cobre, six miles from present day Spanish Town.

On 15 Oct 1655, England officially declared war on Spain—though, obviously, hostilities had begun months earlier. Cromwell gave as his reason for Spanish aggressions against English colonies in the West Indies. With the building of Fort Cromwell, the Point soon grew into a small community. In 1660, the name of the town and surrounding area would be changed from Cagway to Port Royal, and Fort Cromwell would be renamed Fort Charles in honour of the restoration of Charles II to the English monarchy.

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On 4 Jan 1656, General Sedgewick published a proclamation jointly with Admiral Goodson, urging the soldiers to cultivate plots of land that would be allotted for them. Dissension had become common within the army’s ranks, however, and some of the officers opposed the proclamation in a petition, advising instead that England should abandon the island. However, Goodson continued to maintain tight discipline within his fleet, reduced then to nine small men-of-war and four supply ships. 

Even in those early months, Goodson kept his squadron active against Spanish ships. His cruisers often ventured into Spanish waters and captured prizes. On 10 Aug 1655, aboard Torrington, he embarked with some soldiers and a small flotilla. Sailing south from Cagway to the Spanish Main, he took Santa Marta on 3 Oct and, over 15 days, sacked the city and the surrounding area. Unfortunately, there was little in the way of booty, though he did capture 30 guns. As so often happened, the inhabitants of Santa Marta had time to collect their valuables and flee before the English attacked the city. Goodson also fancied an attack on Spain’s stronghold at Cartagena but thought better of it. He lacked a large enough force to ensure victory, so he returned to the Pont.

Christopher Myngs | by Sir Peter Lely

Goodson set sail again in early April 1656 with 10 ships. His second-in-command was Christopher Myngs (1625-1666), captain of the 52-gun frigate Marston Moor. Myngs had arrived at Cagway in January 1656. 

This time, Goodson cruised the Caribbean looking for Spanish ships and ended up at Riohacha (Rio de la Hacha), a port of some importance in Columbia. Again forewarned, the Spanish inhabitants had time to escape with their belongings to the hills and nearby woods. As at Santa Marta, there wasn’t much plunder—four brass cannons and not much more. 

Leaving Riohacha in flames, Goodson sailed down the coast, and, after stopping at Cartagena without attacking it, he returned to Jamaica. On his way, Goodson captured two small Spanish ships. Goodson also made unsuccessful attempts against the Spanish plate fleet in 1656 before retiring to England in early 1657, complaining of ill-health. Myngs followed him there a month later with three ships, including the Marston Moor. Before leaving for England, however, Goodson did make one more considerable contribution to the new colony of Jamaica. 

In October 1656, under Admiral Goodson’s command and encouragement, about 1,400 planters, their families and their servants sailed to Jamaica from Nevis. Nevis was an English colony that had become overcrowded. The newcomers settled at Morant Bay on the eastern tip of the island. This came at a time when Jamaica was in dire need of settlers who were loyal to England.

Before his death on 24 May 1656, Sedgewick had grudgingly supported Goodson in his strikes against the Spanish Main. He left little doubt, though, he thought them unseemly and unprofitable—not even worth the powder and shot expended. Goodson was a capable and courageous officer, and there is no doubt that he operated under difficult circumstances. Nevertheless, he did seem to lack that special instinct required in a commander-in-chief that might have allowed him to maximize his opportunities. Fortunately for Jamaica, his successor suffered no such handicap.

General Sedgewick’s death had placed Colonel D’Oyley in command of the colony. But once again he was superseded, this time by the arrival of Major General William Brayne. Brayne, however, died suddenly in September 1657, leaving D’Oyley again in command.

Commodore Christopher Myngs returned to Jamaica on 20 Feb 1658 for his second tour of duty. Myngs, who was no less active and, perhaps, more enterprising than Goodson, received a cordial welcome from D’Oyley, who was not as troubled by scruples as Sedgewick had been.

As the new commander-in-chief of Jamaica’s naval squadron, Myngs quickly made his presence felt. His first action was along the north coast of the island, where he repelled an invasion by Spanish forces. Next, with a few hundred soldiers on board his ships, Myngs sailed from the Point on a ten-week cruise to retaliate against Spain. With him were the Marston Moor, the Hector, the Coventry, the Blackamoor and the Cagway.

That same summer, Myngs took and sacked the port town of Tolú in present-day Colombia. His squadron had also landed at Santa Marta, which had been sacked by Goodson in 1655. But the Spaniards had not repopulated the town, and although his men marched several miles inland, they found little of value. On his return voyage to the Point, Myngs’s squadron intercepted and captured three Spanish merchantmen. He sailed these prizes to the Point and sold them to men who would become formidable privateers and deadly foes of Spain: Robert Searle, Dutchman Laurens Prins (aka Lawrence Prince) and John Morris. Morris and his son, whose name also was John, became two of Harry Morgan’s closest friends and comrades in arms.

Christopher Myngs’s assaults on the Spanish Main and his taking of Spanish merchant ships were accomplished with the approval and support of the English authorities at Cagway. They believed he had acted legally. So long as England continued to be at war with Spain, and so long as prizes were brought in to the Point to be condemned at the Admiralty Court there, any private citizen with a duly authorized letter-of-marque could make war on Spain and do so with impunity. This was the English government’s official position and, by extension, that of their representatives in Jamaican.

Besides, Myngs’s actions, which resulted in “more plunder than ever was brought to Jamaica,” stood in contrast to Goodson’s less profitable efforts. And this point wasn’t lost on the residents of Cagway, who began to realize just how lucrative war with Spain could be. By 1658, Myngs had become a national hero and model for others at Cagway. More buccaneers and former soldiers volunteered to join his expeditions, increasing his capacity to attack larger, more prosperous Spanish settlements.

Continued …