The Western Design: Oliver Cromwell's disastrous campaign in the Caribbean

Cromwell and the new republican government were determined to carve out a slice of this wealth. In the previous century, English raiders like Francis Drake had spread fear throughout the Spanish Americas through their piratical assaults. However, this would not be a simple smash-and-grab raid, but one of conquest. By capturing Spanish colonies with their infrastructure intact, Cromwell hoped to secure an overseas English empire and bankroll his war-weary nation.

Men of the Western Design

As the plan developed, it was referred to as the “Western Design”. Cromwell even gave it a pseudo-moral objective: to free the Indigenous peoples of America and the Caribbean from “the Popish and cruel inquisition, bringing in the light of the Gospell and the power of true religion and Godliness into those parts”.

With 38 warships and up to 3,000 soldiers – ready to be joined by thousands more in Barbados – this was the largest English overseas military expedition since the Hundred Years’ War. Commanding the fleet would be Admiral William Penn, a man who the diarist Samuel Pepys referred to as both false and impertinent. Penn was known for maintaining correspondence with exiled Royalists (his loyalties once fell under suspicion, leading to him being briefly imprisoned). Nevertheless, he was a competent sailor who had proved himself in the recent Anglo-Dutch War.

The army command went to General Robert Venables, a veteran of the Cromwellian expedition to Ireland. Though he was not the most distinguished Parliamentary officer, he was proficient at governing (he was a workaholic who slept barely four hours a night). Cromwell likely picked him for his administrative rather than military qualities.

With 38 warships and up to 3,000 soldiers – ready to be joined by thousands more in Barbados – this was the largest English overseas military expedition since the Hundred Years’ War

Sailing with Venables and Penn would be a special group of three civilians reporting directly to the Protector, none of whom could be relied upon for great military wisdom. All five men would have an equal say in the running of the expedition. Warfare via committee is rarely an efficient method of fighting.

If the command structure was questionable, then so was the state of the troops. The ranks were filled with raw recruits and soldiers that existing regiments felt they could do without. This was not the fearsome New Model Army of the Civil War, but a force that was largely expendable.

Cromwell knew that tropical diseases in the Caribbean were the death of European armies. The Parliamentary Republic in England was beset by enemies at home and abroad. Experienced soldiers could not be spared – especially when most of the force would die of malaria and yellow fever anyway. To send raw troops was a heartless calculation, but one that Cromwell was by now well used to making.

• Read more | The dark truth about Oliver Cromwell

The expedition departed England in December 1654 and took over a month to reach English Barbados. After obtaining more than 5,000 extra recruits (again, of dubious quality) from the colony, the whole fleet sailed to Hispaniola – the modern-day Dominican Republic and Haiti – to mount an attack on the main Spanish settlement Santo Domingo.

Penn complained the soldiers had “no discipline at all, but every one doth what he lists, and the officers as bad as the men.” Venables’ wife, accompanying her husband, was even more damning when she condemned the whole force as “a wicked army” composed of “the Devils instruments”.

Shooting at fireflies: the Hispaniola disaster

On 13 April, the fleet was within sight of Santo Domingo and prepared the army for landing. A heavy surf got up. Penn refused to risk the ships’ boats despite Venables’ urging. Confusion reigned, with the force eventually being landed around 25 miles from the city. To get to it, they would have to march without guides along a single track through swampy ground. To make matters worse, because promised store ships had not arrived, the march would be made without supplies or adequate water in the fierce Caribbean heat.

When the inevitable Spanish ambush came, lancers charged the vanguard of the English column and a rout quickly ensued. Major-General Heane, a New Model Army veteran, waded into the fleeing soldiers brandishing his sword and screamed “stand but ten men and we shall beat them!” Only two stood with him, and the small group were quickly isolated and lanced by Spanish horsemen.

Venables, now wrecked by dysentery, needed help even to stand, and was unable to organise a defence. Perhaps as many as 600 men were cut down in the rout, with the slaughter ending only when the lancers “were wearie of killing”.

Major-General Heane, a New Model Army veteran, waded into the fleeing soldiers brandishing his sword and screamed “stand but ten men and we shall beat them!” Only two stood with him

The whole army might then have disintegrated were it not for the actions of Penn’s Sea Regiment, a precursor to the Royal Marines, who made a determined stand and shot down many Spanish soldiers.

Despite the best efforts of the Sea Regiment, as the beaten English force trudged its way back to camp, all hope of taking the city evaporated. The men were so unnerved that night that they fired a ragged volley at a swarm of fireflies when they thought them “the enemy with lit matches”.

As the days passed, meagre supplies dwindled even further. The starving men ate anything they could, including dogs and rats. Foraging parties brought back cassava roots, which are poisonous unless properly cooked. Horse flesh by this point was considered “a great delicate”.

Death, disease and desertion

Disease reared its ugly head, and before long the “bloody flux” (dysentery) was killing at least 40 men per day. By the time the soldiers finally embarked on 4 May, well over 1,000 men lay dead on Hispaniola.

To go home now in abject failure would mean disgrace. In a joint conference aboard Penn’s flagship, the committee determined to mount a do-or-die attack on Spanish Jamaica. Sick, exhausted, and thoroughly demoralised, the expedition limped even further into the Caribbean.

Jamaica was a very different proposition from Hispaniola. Spanish authorities had never given the island much thought, so it was barely fortified. The garrison consisted of 600 militiamen who lived more in fear of the 4,000 enslaved Africans they lorded over than any English military force.

• Read more | The Haitian Revolution: the enslaved Africans who rose up against France

While the Hispaniola landing was botched, the Jamaica landing – directed almost wholly by Penn – was a triumph. Complete surprise was achieved and Passage Fort, the main strongpoint, quickly fell into English hands. Venables stayed on board the flagship and could not even bear to look at his men as they made the landing, so disgusted was he by their previous conduct on Hispaniola. The Spanish forces retreated to the interior, leaving the south coast firmly in English hands.

After this minor success, both Venables and Penn then made the incredible decision to return home, abandoning the army to its fate. Penn used the excuse that he was preserving his capital ships. Venables, to be fair, was now extremely ill and thought unlikely to survive the passage home. Both decided that they were going to blame the other for their failures.

However, both men did survive. Upon their return, they were charged with desertion and discharged from the military – and then imprisoned in the Tower of London by a furious Cromwell. From his cell, Venables lamented: “Why did I go with such a rascally rabble of raw and unexperienced men?”

Building English Jamaica: “plant or die”

Venables and Penn may have quit their posts, but there were still thousands of men stranded on Jamaica who could not use the privilege of rank to escape. Nearly 5,000 miles from home, racked with disease, with little hope of rescue or resupply, and with Spanish guerrillas actively trying to eliminate them, their situation was a desperate one.

Colonel Edward D’Oyley eventually took up command of the beleaguered men, becoming in effect the first proper governor of English Jamaica. Agriculture on the island was underdeveloped. He quickly set about an active campaign of turning swords to ploughshares, encouraging the soldiers to “plant or die”, all the while guarding against Spanish attacks. Soon the English-held territory on the island resembled a series of fortified farms.

Towards Christmas, welcome reinforcements were received from England, but these men were soon dying of fever like the rest. The army rolls for December 1655 are horrifying, with 2,500 men sick out of a force of 4,500.

Nearly 5,000 miles from home, racked with disease, with little hope of rescue or resupply, and with Spanish guerrillas actively trying to eliminate them, their situation was a desperate one

In the face of such suffering, the fit soldiers were left with little choice but to dig in and hold on. Fort Cromwell (renamed Fort Charles after the Restoration) was built at the entrance to Kingston Harbour, where the infamous pirate town Port Royal later developed.

Attempts were made to attract civilian immigrants to the colony throughout the rest of the 1650s. In 1656, 1,600 settlers from English Nevis did arrive, but two-thirds were dead within a matter of months.

Jamaica rapidly acquired a loathsome reputation. D’Oyley tried sending representatives to Massachusetts to ask for immigrants, but they failed to recruit a single person. The colony, like English Barbados, could only seem to attract poverty-stricken men who lived fast and died young.

• Read more | Hell on high water: the rise and fall of the golden age of piracy

Back in England, Cromwell, keen to hold on to his Caribbean prize, ordered droves of poor Irish youths to be shipped to the island as indentured servants, and that the sheriffs of Scotland round up “all known, idle, masterless robbers and vagabonds” for similar transportation. The majority would perish in the first few months of their arrival.

In the end, through sheer necessity, the same soldiers who had broken so completely on Hispaniola managed to carve out a subsistence for themselves in atrocious tropical conditions. It was these “Devils instruments” and their descendants who would become the slave traders and sugar barons of colonial Jamaica.

Others would turn to piracy, morphing into the infamous buccaneers of the late 17th century, led by hot-tempered men like Captain Henry Morgan. With such a pedigree, it is little surprise that Jamaica became such a violent and inhumane portion of the British empire. It would remain under British rule until 1962, when it received independence.

Matthew Doherty is a military historian, writer and teacher