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Barbados: Cavaliers of the Caribbean

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For much of the British Civil Wars the colony of Barbados remained neutral, allowing both Parliamentarian and Royalist exiles to run their plantations and trade side by side. But with the collapse of the king’s cause in the late 1640s matters took a violent turn, as Matthew Parker relates.

A map of Barbados from Richard Ligon's 'A True and Exact History of the Island of Barbados' (1657). Bridgetown abutts Carlisle Bay at the bottom of the map. Click for larger version.It was set to be a new Marston Moor among the cane fields, palm trees and humid heat of Barbados: on one side the Royalist force, with 3,000 heavily armed foot soldiers and 200 cavalry on the field; facing them was a newly landed Parliamentary army of 1,500 soldiers and 150 cavalry. The confrontation in January 1652 was the culmination of a series of frantic manoeuvres, intrigues and betrayals.

The previous five years had seen Barbados transformed. The isolated and empty Caribbean island had originally been settled by a small party of about 50 ambitious Englishmen in 1627 with a view to using it to grow tobacco and thus replicate the success of the Virginia colony to the north. But the Barbados leaf had proved to be of very low quality and the 1630s saw a ‘Starving Time’, as new arrivals hoping to escape the severe economic downturn in England poured in only to find survival precarious. Most were impoverished and about half were indentured servants – men or women who had sold their labour for up to ten years with the promise of a small patch of land at the end of the period. Cotton, ginger and indigo were tried, with mixed results. Then in the mid-1640s, helped by Dutchmen fleeing Brazil, a new crop was grown by James Drax, who as an 18-year-old from a humble background had been one of the first settlers and now owned an estate in St George’s parish (astonishingly, the plantation is still owned by the same family, the latest scion of which is now MP for South Dorset, Richard Drax). Drax’s first attempts at sugar harvesting and processing were a failure but by the end of the 1640s the complicated procedure had been mastered and with the sugar price sky-high the island was suddenly ‘one of the richest spots of earth under the sun’. In the 20 months before the end of the decade the total value of Barbados exports had reached the amazing sum of £3,097,800.

While the fabric of the British Isles from countries to cities, to towns and even to families was torn apart by the Civil Wars, Barbados, for a long time, had remained isolated from the conflict. Refugees from both parties washed up on the island’s shores where a very English agreement was in place: don’t mention the war. There was even a jokey forfeit for anyone who did: the compulsion to provide a roast turkey dinner for anyone within hearing. By the late 1640s there were recognisable groups – Roundheads led by James Drax and Royalists led by the refugee aristocratic Walrond brothers, Humphrey and Edward – but friendships and marriages crossed the divide and for now, for the planters, principles came second to growing sugar, trading with whomever they liked (particularly the Dutch) and getting rich fast.

There was also an element of self-preservation about the unity of the white elite planters. The advent of the ‘Sugar Revolution’ had seen small proprietors squeezed out of their holdings by the consolidation of large cane-growing estates and English and Irish servants working the fields in the scorching sun treated with ever more brutality. From the earliest days Barbados society had been turbulent, violent and drunken. Now, thanks to sugar, it became a place of coercion and radical inequality.

In 1649, provoked, as a contemporary wrote, by ‘extreme ill-usage’, the white servants had schemed to rise up, cut the throats of their masters and seize control of the island. The plot was betrayed and nearly 20 ringleaders hanged. Meanwhile another threat emerged. Planters like Drax had found that Africans, imported as slaves, were better workers and hardier than the poor whites on whom they had relied for labour (a third of white emigrants to the Caribbean died within three years). Thus by 1650 there were 6,000 enslaved Africans in Barbados, alongside the 24,000 whites, and the number of blacks was increasing at a furious rate (a process that would eventually lead to some of the sugar islands having as many as 18 enslaved Africans to each white person). The price of tyranny is eternal vigilance, as they say, so rich planters stuck together and took to building their houses ‘in the manner of fortifications’, with ‘Lines, Bulwarks, and Bastions to defend themselves, in case there should be any uproar of commotion in the Island, either by the Christian servants, or Negro slaves’. All adult white males were compelled to serve in the island’s militia, which was officered by the leading planters, as much to police the growing number of slaves as to protect the island from foreign invasion.

A combination of the preponderance of Royalists arriving in Barbados in the late 1640s as their cause failed at home and shock (or ‘heartburnings’ in the words of a contemporary pamphlet) at the news of the execution of Charles I in January 1649 brought this unity among the elite to an end. Gathering impressionable young Cavaliers to their cause, the Walrond brothers looked to the events at home to give them a chance to take control of the island. Their first move was to have the island’s treasurer, Colonel Guy Molesworth, arrested on trumped up charges, banished and replaced with their protégé, 27-year-old Major William Byam, who like the Walronds had been captured on the surrender of the Royalist enclave of Bridgwater, Somerset in July 1645 and briefly imprisoned before fleeing to Barbados. Byam, described by a fellow Barbadian as a ‘known malignant’, was now given responsibility for the island’s arsenal and defence. In the meantime, pretending a Spanish threat, the Walronds had the island put on alert with their supporters in charge of the militia.

Drax and his Roundhead allies still had enough clout to block a proposed alliance with Bermuda, which had declared for the king in late August 1649 and whose representatives now came to Barbados requesting official support and arms. The Walronds responded with a pamphlet offensive. Bills started appearing all over the island, announcing the threat of a Roundhead plot and attacking in particular ‘Colonel Drax, that devout Zealot of the deeds of the Devill’. One Royalist pamphleteer promised to not rest until he had ‘sheathed my sword in [Drax’s] Bowells’. Another declared: ‘My ayme is Drax, Middleton and the rest. Vivat Rex!’  

It was no idle threat. The Royalists were now openly arming themselves and soon a well-mounted troop was at large in Humphrey Walrond’s parish of St Philip. The Cavaliers rode about swearing to slaughter all ‘the Independent doggs’ who refused to ‘drink to the Figure II’ (Charles II).

The island’s governor, the elderly and indecisive Philip Bell, tried to put a lid on the growing unrest by publishing a declaration on April 29th, 1650 ‘That no man should take up Armes, nor act in any hostile manner upon paine of death’, but it was too late. The following day the Walronds persuaded two ‘credulous’ militia leaders, Colonels Shelley and Reade, to mobilise their men to prevent a supposedly murderous plot by the ‘Independents’. Bell ordered them to send their soldiers home but they refused, at which point the governor turned to Drax requesting that he raise his own force to preserve the peace.

Drax briefly held Edward Walrond and Major Byam under arrest but he could only rally about a hundred men, far fewer than were now marching on Bridgetown under the king’s colours with Humphrey Walrond at their head. There was no option left to Bell but to agree to the humiliating terms demanded by the Walronds: complete Cavalier control of the arsenal and the person of the governor himself; the disarmament and punishment of the Roundheads; and a declaration of loyalty to Charles II. The last was publicly made on May 3rd, 1650.

It had been suggested by Byam that it might be safer simply to kill all the island’s Roundheads lest they stir up trouble in England, but in the end most were banished and lost their estates. Drax was one of the first arrested, confined to his estate under armed guard. His neighbour Thomas Middleton was also seized, along with 90 more ‘delinquents’. Drax was fined 80,000 lbs of sugar, twice as much as anyone else, and left for England soon afterwards. Others, perhaps with less local status, suffered more. A Captain Tienman and a Lieutenant Brandon were disenfranchised, their plantations seized, their tongues cut and their cheeks branded with the letter ‘T’ for traitor before both were banished. Another, John Webbs, ‘had his ‘tongue ... bored through with a hot iron’. In the meantime the Cavaliers celebrated by requisitioning all the island’s best horses and toasting their victory in lavish style. At one single feast, it is reported, ‘vast quantities of Flesh and Fish’ were consumed, along with a thousand bottles of wine.

Francis, Lord Willoughby, appointed Governor of the 'Caribbee Isles' by the exiled Charles IIThe Walronds’ violent reign was to be brief, however. At the end of July 1650 Francis, Lord Willoughby arrived, having been appointed by Charles II as the new Governor of the ‘Caribbee Isles’. Willoughby, who was then in his late 30s, had started the Civil War as a Roundhead but had switched allegiance to the king after falling out with Cromwell. Having fled England in 1647 he later served as vice admiral of the fleet that had recently gone over to the king’s side. This had seen his substantial English estates in Lincolnshire sequestered and with ‘all gone at home,’ as he reflected to his wife, ‘it is time to provide elsewhere for a being.’ As for so many from all levels of society who had failed in England, the West Indies provided him a second chance.

Once he succeeded in getting the Barbados planters to accept his authority, Willoughby urged moderation, ending all sentences of banishment and dismissing the Walronds from official civil and military positions. In an attempt to secure an agreement with Parliament he sent a Barbados planter George Marten, whose brother Sir Henry had been one of the regicides, to London to start negotiations. But by now news of the outrages against the Roundheads had reached England along with a number of refugees including James Drax, his brother William and Reynold Alleyne, another influential Parliamentarian.

Parliament responded by pronouncing the islanders ‘notorious robbers and traitors’ and, in October 1650, by ordering a trade embargo, which also included other rebellious Royalist colonies: Bermuda, Antigua and Virginia. The embargo covered not only English vessels but ‘All Ships of Any Foreign Nation whatsoever’. Indeed, its primary purpose was to attempt, unsuccessfully, to stem the flow of arms and ammunition from Dutch vessels to the Royalist American colonies. Then in the same month it was resolved in London to send a fleet to subdue Barbados; by January 1651 the force was ready. In command was Sir George Ayscue, an experienced and pragmatic naval leader, described as ‘a very honest gallant man ... of few words’, which he spoke in a thick Lincolnshire accent. Ayscue, although linked by marriage to one of the leading Royalist families of Kent, had been one of the leading opponents of the 1648 naval revolt.  

Willoughby heard about the Ayscue fleet the following month and, believing the Royalist cause to be far from lost, determined on resistance in spite of the contrary advice of his wife in England. ‘If ever they get the Island’, he wrote to her, ‘it shall cost them more than it is worth before they have it.’ Defiant messages were sent to London. Why should Barbados obey ‘a Parliament in which we have no Representatives, or persons chosen by us?’ Willoughby asked, anticipating the demands of the North American colonies by nearly 150 years. In the meantime he raised men, improved the island’s coastal fortifications and bought weapons and ammunition, mainly from the Dutch but also from smugglers from New England (whose Puritan leaders had declared for Parliament, but, as would prove highly contentious later, were far from averse to trading with the enemy).

Tied up with operations against Royalist privateers through the spring and early summer, the English navy finally sailed for Barbados in August 1651. It left Plymouth having been joined by five merchant ships organised by the exiled Barbados planters and almost certainly armed. Besides these the fleet had seven warships carrying 238 guns and somewhere near a thousand men. Roundhead refugees had reported that conquest of the island would be easy.

In fact Willoughby now had a considerably larger force at his disposal – around 6,000 foot and 400 horse. Early October 1651 saw him in confident mood. Prince Rupert’s Royalist flotilla was on the way to the West Indies, it was believed. Wildly inaccurate news had just arrived via a Dutch ship that Charles II was at the head of a victorious army only 40 miles from London, that the population had risen to support him and that Cromwell was dead. The Ayscue fleet, it was reported, now consisted of nothing more than desperate refugees from a defeated cause. On October 15th there were widespread celebrations across the island, with bonfires, dancing and feasting. Willoughby enjoyed himself at a huge evening banquet at a plantation outside Bridgetown.

But, while the governor was feasting, the Commonwealth fleet had arrived in darkness beyond the beaches of the West coast. Early the next morning three ships from the fleet under its second-in-command Captain Michael Pack sailed into Carlisle Bay, Bridgetown’s harbour. There they found at least 11 Dutch merchantmen illegally trading with the island. Although most were heavily armed, such was their surprise that almost all surrendered straightaway. Hearing the news Willoughby rushed to the town and communicated to Ayscue that he would not surrender the island without a fight. The rest of the fleet then sailed into Carlisle Bay, ‘within half musket shot of the chief fort,’ as Ayscue reported, ‘very free with their shot which was as readily answered’. A large number of longboats, packed with troops, was launched from the ships but, as an eyewitness recounted, ‘so great was the repulse which they received, that they was inforced to make good their Retreat, with the loss of 15 men, and to betake themselves for sanctuary to their ships again’. This resistance was ascribed to the personal influence of Willoughby, who ‘Rides the Rounds in person ... from Fort to Fort’. So it was stalemate, with the Parliamentarians dominant at sea and the Royalists clearly superior in land forces.

Ayscue sent a message to Willoughby that ‘Parliament [was] anxious that the people of Barbadoes should be sharers in the liberty which has been purchased at the expense of so much blood and treasure,’ but the governor replied that he ‘acknowledges no supreme authority but that of the King over England, and is resolved to defend the island for His Majesty’.

Heavily outnumbered on land and experienced enough to be wary of the risks attendant on a major amphibious attack, Ayscue now opted for a policy of blockade and persuasion. Swimmers were sent by night across the warm waters separating the fleet from the beach to collect intelligence, contact Roundhead sympathisers and, by raising the alarm, keep the defenders in a state of constant, wearying readiness; leaflets were distributed urging the island’s inhabitants to come to their senses; James Drax, who had returned with the Ayscue fleet, was smuggled ashore to contact moderate Royalists among his friends, including the influential planter, Thomas Modyford. When it reached Ayscue on November 8th the news of the final defeat of the king’s cause at Worcester was communicated to Willoughby, who responded by writing that he had ‘never served the King in expectation so much of his Majesty’s prosperous condition as in consideration of his duty’. Nonetheless he did admit that the news did ‘not please him at all’.

But Ayscue now had his own problems. After months at sea his men were so scurvy-ravaged that he had hardly enough fit to crew his ships. A more active policy was signalled by the launch of a surprise attack on November 22nd against Royalist positions around Holetown midway up the west coast. Two hundred men landed by night and got the better of a detachment of militia, spiking guns and taking 30 prisoners. On December 1st the Parliamentary fleet was joined offshore by a large force of 15 vessels on its way to Virginia to suppress Royalist rebellion there. With Ayscue determined to use the newly-arrived troops while he could, on the night of December 17th, 450 men under the command of Colonel Reynold Alleyne, the Barbadian Roundhead, raided Speightstown towards the north end of the west coast. The Royalists responded quickly and during the fierce engagement that followed Alleyne was killed, hit in the throat by a musket ball. In the confusion of darkness the defenders, who numbered over 1,000, overestimated the size of the landing party and faced with ‘ye Seamen runninge in wth halloweinge and whoopinge in such a ffeirce disorder yt ye Enemye was soe amazed yt after a short dispute they all ran’. A hundred Royalists were killed and 80 taken prisoner along with guns, small arms and a quantity of gunpowder.

The Virginia detachment could not linger due to their lack of water and provisions and so Ayscue could still not risk facing Willoughby in a pitched battle. However his propaganda and the efforts of Drax were at last paying dividends. On January 6th the Royalist moderate Thomas Modyford drew up his regiment of 1,000 musketeers and 120 horse and persuaded them to declare for Parliament. Contact was made with Ayscue, who landed his much-diminished force at Oistin’s Bay at the southern end of the island, whence Modyford marched to meet him. Together they had about 1,500 foot and 150 horse. Willoughby advanced to within a mile of them.

On paper Willoughby’s forces were still far superior, but Ayscue’s attritional blockade and propaganda had done their work. Nearly half of the Royalist army had melted away, leaving about 3,000 foot and a couple of hundred horse. Morale in the surviving ranks was low: they were tired out by constant night-time deployment; it was unbearably hot and humid. After brief contact Willoughby fell back a couple of miles; then, suddenly, a torrential tropical downpour began. The long-awaited battle was a wash-out – ‘through continual extremity of rains, the soldiers could scarcely keep a match lighted’, as Captain Pack reported. Ayscue was unable to advance to engage the Royalist forces but at last Willoughby’s resolve failed. After three days of heavy, almost constant rain, the Royalist commander, ‘seeing that the fire is now dispersed in the bowels of the island’, asked for a ceasefire.

The confrontation may have been anti-climactic but its long-terms effects were anything but. On January 11th, over drinks at the Mermaid Tavern in Oistins, the closest the island had to a place of assembly, a settlement was agreed whereby Barbados accepted the suzerainty of Parliament. In return Ayscue offered the right of the islanders to continue to trade with whomever they liked. But soon after the agreement it was made clear by Parliament that a new approach was in place, based in part on the terms of the embargo of October 1650. Why should Dutch traders pocket the margins to be made in shipping English-grown sugar to Europe? In keeping with the principles of mercantilism, the dominant economic orthodoxy of the time, and inspired by the example of Barbados and wider frustration with the United Provinces, the First Navigation Act of October 1651 demanded that sugar and other colonial goods could be imported into territories of the English Commonwealth only by English vessels or those from the country producing the goods.

The Navigation Act marked an important new imperial direction. Before this time the English colonies had been an informal association, bound together only by trade, families and shared cultural background. Business and effective government was in the hands of a rickety structure of royal monopolies, private individuals of many nationalities and private charters. But the events in Barbados had drawn the metropolis into colonial affairs. Now trade and empire was to be regulated – and vigorously expanded – ‘in the national interest’.

In this new climate of economic nationalism Parliament was prepared to go to war to defend or expand the commercial interests of England. This is precisely what happened in July 1652, when conflict broke out with the Dutch. Commercial advantage was replacing religious or dynastic differences as the main cause of wars between the great powers, with the valuable sugar islands of the Caribbean their constant theatre.

As intended, the Navigation Act marked the beginning of a process that saw England’s merchant marine rise to international pre-eminence. The resulting pool of skilled seamen provided crews for the world’s most powerful navy. At last, London began to rival Amsterdam as a centre of commerce. But the cost of this policy was borne by the English consumer, who paid higher prices for imported goods. The restrictions of the Act and its successors not only caused a nightmare for those charged with enforcement, it also sowed the seeds for conflict that would culminate in the loss to the empire of the North American colonies.

Matthew Parker is author of The Sugar Barons: Family, Corruption, Empire and War (Hutchinson, 2011).

Further reading: 
  • Gary A. Puckrein, Little England: Plantation Society and Anglo Barbadian Politics, 1627-1700 (New York University Press, 1984)
  • Carl and Roberta Bridenbaugh, No Peace Beyond the Line: The English in the Caribbean, 1624-90 (Oxford University Press, 1972)
  • Larry Gragg, Englishmen Transplanted: The English Colonization of Barbados, 1627-1660 (OUP, 2003)
  • Richard Dunn, Sugar and Slaves: the Rise of the Planter Class in the English West Indies (University of North Carolina Press, 1972)
  • N. Darnell Davis, The Cavaliers and Roundheads of Barbados, 1650-1652 (Argosy Press, 1877)
  • Nicholas Foster, A Briefe relation of the late Horrid Rebellion Acted in the Island of Barbados (London, 1650)
  • Richard Ligon, A True and Exact History of the Island of Barbados (London, 1657)


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