Chapter 3.1 – Conquest of Jamaica

Spanish resistance on the newly captured and renamed island of Jamaica took the form of a prolonged guerilla war led by Don Christobal Arnaldo de Ysassi and by two “Spanish Negros,” Juan Lubolo (aka Juan de Bolas) and Juan de Serras. Ysassi had been given a commission as governor of Jamaica, making him the last Spanish governor of the island. Their guerilla armies comprised former Spanish settlers, who had chosen not to flee to Cuba, and of Cimarrons—freed and runaway slaves—later known as Maroons. From strongholds in a large area of rugged hills and pasture lands on the north side of the island, the Spaniards waged a long, costly war. 

From 1655 to 1660, Ysassi made several unsuccessful attempts to recapture Jamaica. From time to time, small bands of Spanish soldiers landed to reinforce the guerillas. They came from Havana, San Domingo and Porto Rico. They were joined by Santiago’s former residents, who had fled to Cuba immediately after the English invasion but returned to join in the resistance. 

Harry Morgan was one of the fortunate few among the new English colonists to survive frequent outbreaks of malaria, yellow fever and dysentery in those first five years. For much of this period, the Spaniards controlled the mountainous interior and most if not all of the north coast. From there, they successfully staged raids on new English plantations, limiting the ability of the invaders to grow crops to augment supplies shipped to them by sea. The Spaniards also harried and ambushed those who ventured into the hills searching for cattle that had been released and driven there to deny the invaders a ready supply of fresh meat.

When the English had first arrived, fresh meat was readily available from the abundant supply of cattle abandoned by the Spanish. Most of these had either been wastefully slaughtered by the invaders or driven deep into the rugged highlands. English war parties passing through dense woods and rocky gorges searching for fresh meat and guerillas were ever in danger of ambushes. Accordingly, their soldiers tended to remain near their own strongholds on the southeast portion of the island. 

Sources claim that, at times, the invaders were quite literally starving. They survived on a diet that included dogs, rats, snakes and iguana lizards. Of the original 7,000 to 8,000 soldiers, barely 4,500 (and I’ve seen lower estimates) survived their first year on the island. Those who did survive had little choice: toughen up or die. And, from what we know of young Harry Morgan’s later life, we can be sure he chose the former. Considering his family’s military tradition, and given the manpower shortage, we can assume that Ensign Morgan participated in the guerilla war. Harry would have served under the command of the de facto governor, Colonel Edward D’Oyley (1617–1675). 

When Penn and Venables departed Jamaica, they left Vice-Admiral William Goodson as naval Commander and Major General Richard Fortescue as commander of land forces, but Fortescue died of fever in October 1655. That same month, Major Robert Sedgwick arrived at Jamaica to take up the post of civil commissioner, superseding D’Oyley. A few months later, Sedgwick received Cromwell’s commission as major-general and commander-in-chief, but Sedgwick died in June 1656. Sedgewick’s sudden death placed D’Oyley once again in command until he was again superseded by the arrival of Major General William Brayne. Brayne died in September 1657, leaving a blank commission, given to him by Cromwell, that Brayne had filled in with D’Oyley’s name.

When Brayne arrived, he brought a thousand recruits with him. This did little to improve the situation, however. Brayne reported in the following April:

The soldiers are forced to neglect the strictness of their martial duty by rambling abroad to seek a livelihood; so that if the enemy from Spain should attempt us in this condition, I greatly fear the soldiers would make but a weak resistance, their spirits have been so dejected for want of necessary food and raiment. But many of the officers seem resolved (through the assistance of God), to sell their lives as dearly as they can. [Source: Cundall, Jamaica under the Spaniards, p. 56.]

However, over time, the tide of war began to ebb for Ysassi as English tactics evolved. On land, D’Oyley’s men became better at anticipating and defending against ambushes. They also began using their ships to better effect. English commanders, rather than risk Spanish ambushes on inland trails, used ships to transport their men around the eastern end of the island and attacked the Spaniards at strongholds like St. Ann’s Bay. They used ships to cut supply lines from Cuba and elsewhere and reduce the opportunity for reinforcements reaching Ysassi.

Then came the crucial battle.

Harry Morgan may have been present at the most important battle ever fought on Jamaican soil, the Battle of Rio Nuevo, when Edward D’Oyley defeated a large force under Ysassi’s command at Rio Nuevo on the north shore in late June 1658. The English killed more than 300 Spaniards and captured great quantities of food and arms, including much-needed cannons that the English used to strengthen their own fortifications. 

Ysassi and the remnants of his force withdrew inland to the hillsides and forests. They held out until 26 Feb 1660 when Lieutenant-Colonel Tyson, with a party of eighty men, surprised Ysassi’s camp near Moneague. Ysassi’s lieutenant and fifty others of his men were killed. 

Following that engagement, the two sides began negotiations for a treaty of surrender, but they could not reach an agreement. The final blow came, though, when the English captured a boat, bringing supplies to Ysassi, in the bay at Ocho Rios. That loss was crucial to Ysassi and made it painfully obvious to him that further resistance was hopeless. 

Ysassi and what was left of his followers fashioned two large canoes from silk cotton tree logs, and, using improvised sails, they left the island from the little north-coast harbour we know today as Runaway Bay. From there, they crossed a hundred miles or so to safety in Cuba. With their departure, Spanish rule over Jamaica came to an end. Not until 1670, however, did Spain officially cede control of Jamaica to England. This was done under the Treaty of Madrid.

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Since leaving England, Harry Morgan’s military education directly influenced his future success as a leader of irregular military forces. He’d learned how to lead men across difficult tropical terrain, live off the land and, especially, how to detect, avoid and defend against ambush while doing so. He’d also learned the value and limitations of naval power against land-based installations. 

Moreover, Harry Morgan had ample opportunity to assess the different military strategies and tactics of tropical warfare used by Ysassi’s guerillas and by his own commanders. He learned how he could adopt and adapt these for future use. Most importantly, this time allowed Harry to develop lifelong friendships and allegiances with others who had accompanied Venables to Jamaica. As we will see, these friendships with men like his future brothers-in-law, Robert Byndloss and Henry Archbould, would stand him in good stead for years to come.

Though I have found no documentary evidence of Harry’s service in these first five years, I believe it safe to assume he must have served with some distinction for documentation does exist that tells us that, in 1662, he held the rank of captain in the army/militia. (His captaincy was not the navy rank of the same name, which is at least three ranks higher.)