The Western Design was England’s disastrous attempt to conquer Spanish America, starting with Hispaniola, Cuba, Puerto Rico and Cartagena. Instead, after an unspeakably bad defeat in Hispaniola, they ended up with Jamaica. Jamaica quickly became England’s bloodiest colony, and much of that blood came from Irish victims of transportation.
It was a disaster, though, which forced Puritans to question their interpretations of everything they’d just gone through. Then, when Cromwell died a couple years later, it was yet another ominous sign.
Transcript
In 1655, England took yet another step toward becoming an empire. It had passed the Navigation Acts, and submitted its colonies to direct Parliamentary authority, and now it made its first imperial conquest when it took Jamaica from Spain. But though it was a new kind of campaign, the first time England had used its military to advance colonization, the Western Design was a disaster of the type we’ve discussed so many times before. The only difference was that it was on a much bigger, much more horrifying scale.
Introduction
By 1655, things had come full circle in England. There’s a quote, probably the most famous quote used to describe the English Civil War, which says that Parliament had fought to protect a herd of sacred cows, each of which was slaughtered to propitiate the god of war. So Parliament had opposed King Charles’s attempts to raise taxes without public consent, and now they had done the same. He had fought unpopular, expensive wars, and now so had they. He had dismissed Parliament, and on April 20, 1653, Cromwell had also dismissed what remained of it. In fact, he had led an armed force into the House of Commons, much like Charles had in 1642, and said “You have sat too long for any good you have been doing lately. In the name of God, go.”
So, now, instead of a king, England had a military dictator. He and the Army had almost complete control of England, including the unlimited ability to tax. The final cow had been slaughtered, and the world had seen one of its great ironies … for the first time, at least.
But he was in control of a shattered country. After a decade of Civil War, England was now at war with the Dutch. A weary population was growing tired of Puritanism, and Puritans were getting a little tired of waiting for the promised Millennium. Puritanism had never been the majority religion in England, even if it had had an influence on the country’s religious ideas. Holidays, sports, theater, make-up. People missed these things. And they missed the calm, predictable life of the past. The government had no money. Taxes were higher than ever, but the country wasn’t stabilizing.
Cromwell ended the war with the Dutch, and turned his attention toward Spain. There were a few reasons for this. On a religious level, John Cotton had interpreted the Book of Revelation to mean that the West Indies were the “Euphrates,” and that was enough for Cromwell. Even though Cotton had died a few years before, Cromwell had followed his every word. By displacing the Catholic Spanish from the Western Hemisphere, he could promote Puritanism and ultimately pave the way for the Millennial Rule of the Saints, with England as a New Rome in the West, and a New Jerusalem.
On a more secular level, England needed a cause to rally around, and fighting Spain was a popular one. Even the Earl of Warwick came out of retirement to help. He’d been quietly avoiding politics since his brother’s execution, but confronting Spain had always been his pet cause, ever since inheriting his father’s title and Virginia Company shares, he had wanted to eliminate Spain’s American Empire. Former New Englander and Fifth Monarchist leader Thomas Venner, James and William Drax of Barbados, and Maurice Thompson, as well as England’s merchants as a whole, also joined the cause. Even Edward Winslow, the aging Pilgrim, one of the original leaders of the Plymouth Colony, decided to join the expedition, sharing the vision of a South America filled with Puritan towns, each with its own Congregational Church. Another New Englander, Robert Sedgwick, also offered to lead a fleet.
On a practical level, Spain was weak, and at war with France, and if the Western Design succeeded, it would bring in customs revenue that could help fund the English Government. Plus, in theory at least, the Spanish method of Colonization would work in their favor. English colonies were populated by vast quantities of English people, with a vested interest in which government ruled them, but Spanish ones were populated by a relatively small Spanish population. The bulk of the people living in Spanish America were African Slaves and Indian populations, neither of which should have much loyalty to the Spanish Empire. All they’d have to do would be overturn the ruling elite, and in theory the colonies would be theirs.
It was with all of this in mind that Cromwell planned the Western Design, which is the term used to refer to the military expedition that would begin England’s conquest of Spanish America. He recruited leadership from among the most accomplished military figures in England. I’d mentioned Winslow before, and he was joined by former Providence Island governor Gregory Butler, as well as Barbados governor Daniel Searle as commissioners. Leading the secret organization of the mission would be Cromwell’s brother-in-law, John Desborough.
And then, to lead the actual Navy and Army that would cross the Atlantic, would be William Penn and Robert Venables, respectively. Apart from their shared tendency toward extraordinary military success, these two were polar opposites in almost every way.
This is a good opportunity to correct an error I made last episode, and say that we’re not going to be discussing Pennsylvania founder William Penn much today, but rather his father. This William Penn was young, brilliant and ambitious. He was 33 years old, and an almost apolitical person who had waited until he could guess who was going to win, and then joined their side. That meant he’d fought for Parliament, but he had no real loyalty to them. He was simply trying to rebuild his family’s waning fortunes. He was, however, incredibly brilliant. He’d practically been raised on merchant ships, and was a captain, married with a kid on the way, by the time he’d turned 20. By the end of the war, he’d been promoted first to Vice Admiral of Ireland, and then to Vice Admiral of the Straits. He’d helped lead Parliament’s chase of Prince Rupert through the Mediterranean, and he’d fought in the Anglo Dutch war.
On the other hand, Venables was older, and he’d been successful because of his unrelenting devotion to the Puritan cause. When he was badly wounded at the Siege of Chester, he kept fighting and even led the negotiations for surrender. In Ireland, he’d helped defeat the Marquis of Ormond, and then facilitated Cromwell’s victory at Drogheda. Then he’d helped take Ulster, and spent four years fighting Irish confederate guerillas, only returning to England to lobby for his troops to be paid the money they were owed. Cromwell had been personally impressed by him, both in reputation and in fighting alongside him, so he had recommended him to command the Western Design’s land army.
They were given joint control of the mission, sharing power equally and in a slightly ambiguous way, and told in June 1654, along with the rest of the expedition’s leadership, to be ready to sail for the West Indies by the end of the year. Their precise military targets would be Hispaniola, the island home to the modern day Dominican Republic and Haiti, as well as Puerto Rico, Cuba and Cartagena, in modern Colombia, which was the capital city of the Spanish West Indies. The order in which they invaded those colonies would be up to the discretion of Penn, Venables and the commissioners, but seizing those four places was their goal, which when accomplished would provide a base for the invasion of the rest of Spanish America.
And after giving the order, Cromwell, who had previously been obsessively involved with every English military venture, essentially ignored the whole affair. He was getting older, he was distracted by other things, and the reputation of colonization in England was that it was a simple task which was messed up by lazy colonists. Every time an investor had struggled to raise money, since the earliest days of the Virginia Company, that had been the line. Cromwell had put the best of the best in charge, and he had other things to do, so he left his leadership to their own devices.
And while they worked to organize the mission, Penn secretly reached out to Charles II to see if he would be better off defecting, taking his fleet to France and helping the aspiring heir to the throne invade England. Charles, though, said the time wasn’t right. He thanked him for his offer, and encouraged him to go on Cromwell’s errand for now, while he waited for a better opportunity to present itself. The Western Design, in fact, might help Charles, because every enemy to the English Commonwealth would ultimately be an asset for him. Cromwell found out about Penn’s correspondence, but he didn’t care. Penn remained in charge of the Western Design’s naval operations. I can only speculate as to why.
And preparations continued. They needed to get together food, weapons, alcohol, other necessities, as well as a supply fleet to take the stuff. Venables also needed to recruit an army, and Penn needed to man his 38 ship naval fleet. This was easier said than done. Neither naval captains nor army commanders were going to send their best men halfway across the world. Instead, they used Penn and Venables’s recruitment activities as a way to get rid of their worst. They sent the lazy, the insubordinate, the troublemakers, the people they just didn’t want to bother with anymore. These were supposed to be the seasoned veterans who would form the foundation of the military, who would ensure that it was still a professional fighting force even though its numbers would have to be boosted by raw recruits. They just weren’t, though. And those raw recruits who boosted their numbers were, well, described as “common cheats, thieves, cutpurses, and such like lewd persons.”
American colonial ventures had always been largely populated by the types of people who England wanted to get rid of, and that didn’t change with the nationalization of colonization. Neither, for that matter, did the difficulty of gathering supplies.
On December 15, Cromwell ordered the fleet to depart. Venables rushed to London and told Cromwell they weren’t ready yet. They had 500 fewer soldiers than they needed, and only 15 rounds of ammunition per man. The muskets were with them, but the wooden stocks and their pikes were in a storage facility in Deptford. They didn’t have enough food, and they weren’t organized to leave yet. They needed more time.
Cromwell told Venables to get back to his post in Portsmouth immediately, and that if he was still in London the next day, he would be arrested. Then, he summoned Desborough to ask him exactly why his mission wasn’t ready to leave yet. Desborough again explained the situation, and Cromwell was furious. His outburst left Desborough shaken and embarrassed, and included the orders to get to Portsmouth immediately and see to it personally that the fleets set sail, regardless of how prepared they felt.
So he did. And in Portsmouth a couple days later, a very shaken Venables was followed by a very shaken Desborough, who ordered everyone to board the ships immediately. The boarding was utter chaos. Soldiers left their stuff behind, people tried desperately to get their goodbyes in, officers were separated from their men and units split up as people were shoved onto the nearest vessel. Desborough stormed up and down the shore until the ships were boarded and had pulled away from the docks. The supply fleet wasn’t even loaded, and they could only promise to follow within the next few days.
So perhaps more than any we’ve ever discussed, this trip was off to a sudden and chaotic start.
The trip to Barbados was quick and smooth, though. They arrived six weeks later, and the first thing they saw was a group of 15 Dutch ships trading illegally in the harbor. They captured all of them. This led to a spat between Penn and Venables, though, because they couldn’t agree on who should be put in charge of the spoils. Penn put his own nephew in charge, and refused to listen to either Venables or Winslow’s complaints. This was a naval matter, end of story. Tensions already existed between soldiers and sailors, though, and this only exacerbated them, showing the overt hostility between the leaders of the two factions.
The main issue, though, was to meet up with their supply ships, and for this, they had to wait 10 weeks. In this time, they did learn more about the region. Barbadians gave them advice about which locations would be easiest to attack, and which would be most difficult. Barbadians didn’t particularly like any of the four as a starting point, but rather favored Jamaica. Of the list, though, Hispaniola was probably the best, and Cartagena was absolutely the worst, because it was a mainland city rather than an island. They also bought extra provisions. Their brandy had been lost in a small fire en route to Barbados, so they bought alcohol to replace it. They bought some more food, and they bought more weapons, especially pikes. These pikes, though, were about two feet shorter than European-made ones, which would make them virtually useless in combat.
And, they spent time recruiting soldiers to boost their so-far disappointing numbers. Lewis Morris joined them enthusiastically. There was no one better to have on their side. And then, a lot of poorer Barbadian planters also threw their lot in with the Western Design. Barbados’s transition from tobacco to sugar farming had pushed a lot of colonists there into poverty. Tobacco was a crop that never got you much money, but it could be grown on a small scale, and didn’t require that much labor to grow it. So, a small tobacco farm with an indentured servant or two could sustain you. But with sugar, well, sugar required a huge investment of money and labor, and that meant that a small sugar plantation simply wasn’t feasible. The value of sugar drove up the value of Barbadian land, as the people who had managed to transition to sugar bought out the smaller planters.
Those planters hadn’t had anywhere to go, really. Some had gone to Suriname with Willoughby. Some had gone to Antigua and Nevis. Some had stayed on Barbados and kept raising their less-valuable crops on their small farms, but that was becoming increasingly difficult. Some had hired themselves out as indentured labor for the large sugar planters. These people joined Penn and Venables en masse. And to boost numbers further, Penn and Venables started forcibly conscripting indentured servants and artisans. At the end of the 10 weeks, they had increased their numbers by 4,000.
The expedition had, however, earned the enmity of the local citizens. It was burdensome enough that they’d stayed for 10 weeks, especially because colonists couldn’t continue their sugar trade with the Dutch at the time. They didn’t like the notion of England having a permanent military base in the area which would enable them to monitor the Dutch trade more closely, and they didn’t like the extra tax which Cromwell had authorized Venables to take to fund the expedition. Now, on top of all of that, they’d seized a good portion of the island’s English labor force.
This didn’t really affect Penn and Venables, who went on their merry way 10 weeks later, but it did affect the outcome of Barbados’s next election. Even with only Cromwell supporters being allowed to vote, supporters of the Western Design lost their seats in the Island’s Assembly. Modyford was notably among them.
The fleet now traveled northward through England’s colonial holdings on its way to its Spanish targets. They visited each English island, and recruited more soldiers. They got 800 from St. Kitts, 80 from Montserrat, 300 from Nevis, and at the end of their trip, they had a 7,000 person army in addition to their fully manned naval fleet. Colonial recruits, though, were no better than the English ones had been. And, by the end of this trip, it was clear that Penn and Venables, as well as the sailors and soldiers at their command, hated each other. On St. Kitts, Venables asked for a pike, you know, one of those useless things, so the army could kill some cows to eat, and Penn had refused. Sailors as a whole were refusing to listen to any soldier requests, and the ships were packed so that the alcohol wasn’t even accessible. Buying it on Barbados had done nothing, because no one could reach it to drink.
And, it was hot. So hot. The water was filthy, the food was disgusting, so the health of soldier and sailor alike started to deteriorate. But it was time to decide on a location and make the first attack. And per Barbadian advice, they chose Hispaniola. It was defended by a fairly small garrison, whie being within easy striking distance of everything else. They decided on a meeting location in Santo Domingo Harbor, and on April 13, 1655 they arrived on the southern side of the island.
The problem is, Santo Domingo is home to one of Hispaniola’s coral reefs, and when Penn and his Vice Admiral, William Goodson, realized this, they refused to enter the harbor. Sounding the harbor would draw attention to the attack, and failure to sound would be dangerous. Fair enough.
But then, their solution was to travel 40 miles down the coast and drop the soldiers off there. Not so fair. Venables fought against this, but they simply did not listen to him and did it anyway. They dropped the soldiers, 7,000 of them, off in the middle of the jungle with whatever food they could carry, and no canteens for water. They’d have to depend on whatever water was on the island to sustain themselves during the 40 mile march. Three days later, they reached Santo Domingo. And there, well remember they were short on ammunition and gunpowder, and armed with almost useless weapons. Now, add to that the fact that they had been marching through a jungle with no food or water for three days, so they were exhausted. And Penn’s fleet wasn’t backing them up, like, at all. So, at the beginning of the battle, there were 7,000 English soldiers and 700 Spanish ones. At the end, there were 6,000 English soldiers and 700 Spanish ones. The Spanish soldiers didn’t even have to do much more than walk into the jungle with machetes.
The English retreated and tried to process the magnitude of the disaster. The whole voyage had been going downhill, from the difficulties organizing to the hurried departure from England to the animosity among soldiers, sailors and settlers, but this was far worse than anyone could have imagined. Edward Winslow in particular was so stressed that he died a few days after leaving Hispaniola, and the rest of the people had to decide what to do.
And this is when they started thinking about Jamaica. Barbadian advice had been that Hispaniola was their best bet among options listed, but that Jamaica was a better choice. It was a weak colony, the only Spanish agricultural colony, and was facing a lot of the same issues as early English colonies had faced as agricultural societies. There wasn’t enough food to feed the settlers, much less make a profit, and the people were poor, miserable, disheartened and unhealthy. Plus, it was in a strategic location, at the heart of the Spanish Caribbean and on the major Spanish shipping routes. At the very least, it’d be something to show for their efforts. They weren’t going to get anything else, and owning Jamaica couldn’t be worse than not owning Jamaica, so they went for it.
And this time, things went well. They sailed directly southwest, reached Kingston Harbor before the Spanish even knew they’d arrived, sailed right into the bay, dispatched the army, and swarmed a tiny fort filled with 200 men and three cannons. After a six mile march, they also had its capital, main fort, harbor and beach. The severely ill governor surrendered on English terms, which stated that the Island’s leadership and affluent residents would have to leave, and leave everything valuable with the English, but that slaves, servants, artisans and common laborers could stay as long as they accepted English rule. The governor would be sent to Campeche, in Mexico, but he died on the way.
There was only one problem, and that’s that owning Jamaica was, in fact, worse than not owning Jamaica. It was much, much, much worse, in fact. First, well first you had the disease, scurvy, dysentery, yellow fever. And all of this was exacerbated by good old fashioned starvation. I mean Jamaicans hadn’t had any food. The English hadn’t brought enough food, and it took time to grow, except that a huge portion of these people had no experience growing food in a tropical climate.
And then you had the guerilla fighters who didn’t want to accept the English takeover. Some of these were island leaders who hadn’t wanted to leave and instead stayed to fight. They were led by the governor’s nephew, in fact. And most of them were African slaves. These people were way better at fighting than the Spanish, they were bigger, stronger, faster. And they knew the island better than the English. They set about burning farms, killing animals, and ambushing any person or small group of people who found themselves in the wrong place at the wrong time. Within six months, half the army, 3,000 people, were dead.
It only took a couple weeks before Butler was done. He knew a bad situation when he saw it, and he left. And a couple months after that, Penn and Venables left, too, in June and July, respectively, of 1655. In Venables defense, he was sick, but that doesn’t change the fact that the two had abandoned their posts and left their men to fend for themselves. And when they showed up in England, Cromwell was flabbergasted. He demanded an explanation, they blamed each other, and he was even angrier. He threw both of them in the Tower.
They weren’t imprisoned that long, but it was long enough for Penn’s son to have his first major religious experience. He was 12, and distraught at his father’s situation, until he saw a soft, light-filled figure which filled him with happiness. This would strongly impact the young William. On their release, Penn went to Ireland to settle on his estates there and quietly work for the return of Charles II to the English throne, and Venables went home to Cheshire, stripped of his command, called a coward and humiliated. The real question wasn’t what to do with Penn and Venables. It was what to do with Jamaica.
Penn had left Sedgwick in charge, and Venables had left Fortescue. But then Fortescue died and was replaced by Brayne, and then Brayne died and was replaced by General D’Oyley. And Jamaica, even among the roughest of American colonies, and most war-torn of English counties, quickly got the reputation of being nothing less than hell on Earth. And that reputation was, in itself, a problem, because what Jamaica needed more than anything else was enough people to make it a functional and secure society. And who was going to go there? The Chesapeake had previously been the toughest place, where 40% of arrivals died within a couple years, but in Jamaica it was 50% in six months. This stabilized after 2.5 years, under D’Oyley’s leadership, as some food became available, the guerilla insurgents were driven out, and survivors started to be a little more used to the environment, but it was still awful.
But Cromwell’s government had to try to recruit people. First, he reached out to Barbados. It was a Caribbean island whose inhabitants had been successful. Barbadians were still annoyed by the conduct of the Western Design expedition, and they didn’t like the idea of a competing sugar colony which would also serve as a military base to police their trade with the Dutch. So they not only refused to send people, their government actively opposed recruitment attempts.
Then they looked to New England, which shared a dedication to the same ideological foundation of the Western Design. And the response was, “Well, that’s an interesting idea.” “So you’ll do it?” “Well, no.” Cromwell specifically encouraged New Haven, which had been struggling with the Dutch for land, struggling with overpopulation, and generally in an awkward legal position. He’d already floated the idea of their going to Galway, Ireland to help with the conversion of the Irish, and now he suggested Jamaica. But again they refused.
Then he looked to the Bahamas, where the Eleutherian adventurers lived in abject poverty, scraping by from month to month and year to year. Again, though, they counted their blessings that they weren’t living in Jamaica, at least, and again refused.
And then, he considered transporting rebellious Scottish Highlanders who were causing trouble for the Commonwealth. He had to abandon this idea, though, because if he did it, Scotland as a whole was going to rebel, even the Western colonies which had once supported Cromwell. They can take our lives, and they can take our freedom, our government, our king, our money … but if they put even one of us in Jamaica, we’ll burn this country to the ground.
Jamaica wasn’t going to transform into any sort of a Puritan colony, and the answer to populating it would lay with the Irish. Some English petty criminals were sent there, but it was the Irish who were sent en masse, and they died there, en masse. Somewhere between 30 and 80,000 Irish people were sent to Jamaica in the first few years, and they died so fast that England experimented with sending a group of 2,000 adolescents, in hopes that they’d acclimate faster and survive better. But they didn’t. This was all part of a serious depopulation of Ireland that happened during the Commonwealth Era, as the Irish population dropped from almost 1.5 million to 616,000. A huge part of this population drop was a result of transportation to the Caribbean, and the most common Caribbean destination soon became Jamaica.
That’s not a military base, though. It’s not something that could be used to help take out the rest of Spanish America. It’s nothing that England had gone into the Western Design wanting to achieve. It was another early Virginia, or early Plymouth or early Bermuda, or early Barbados, except that even after improving, it was much worse. And, it was a time, money, resource sink that continued to cost more than it produced for years, and it was costing a government that didn’t have any extra money to waste. Even after a handful of colonists started to relocate from other Caribbean islands, it was nowhere near enough.
England had one remaining option, and that was to allow Spain to retake the island. Spain would likely invade, and they’d stand down, and give up on the whole, bloody affair. But Spain didn’t bother. They’d never gotten anything from Jamaica, and their government didn’t have money to waste either. It was nothing more than a resource sink, so let it be England’s.
And that’s how the English ended up with Jamaica. Two exhausted powers had fought over an island that neither one really wanted, and depending on your interpretation of victory, England had won. Things had spiraled out of control, tens of thousands of people were dead, and they had nothing to show for it. This really shook England, and it really shook Cromwell, too.
Cromwell had seemed undefeatable. His military and later political victories hadn’t just been the stuff of legend, they’d been the stuff of prophecy. His supporters had pinned their hopes on the belief that this meant the Millennium was coming, and that Cromwell was the man who would prepare the world for Christ’s return, maybe with England as His New Jerusalem, just throwing that out there …
But this defeat, and all the disasters which followed, called all of that into question. Cromwell seemed to have had God’s support before, so why had that changed? The answer had to be sin. Some sin had caused God to remove His favor from England.
Cromwell felt that the sin must lie with the English people, and he called for a time of fasting and prayer to identify what it was. Henry Vane, though, had a different explanation. He said the sin lay with Cromwell, who had turned England’s great Republican government into a military dictatorship. The sin of the nation had been abandoning Republicanism, and Vane wrote that he hoped the defeat, and the “broken, contrite, and self-denying frame of Spirit” that it had brought would prepare people to bring it back. This was a bold move in a dictatorship. Vane was thrown in prison, and the publishing of pamphlets echoing his sentiments was forbidden.
Less dramatic, but extremely reasonable, was Robert Sedgwick’s explanation. Sedgwick said that no Godly society could be built on a foundation of privateering. Privateering had been an integral part of the strategy of the Western Design and its proposed aftermath, so Sedgwick had seen it first hand, and he said it wasn’t “honorable, that your highness’s fleet should follow this old trade of West India cruisers and privateers, to ruin and plunder poor towns, and so leave them.” He said the practice gave the English a bad name among the very Indians and slaves they were coming to protect and convert, because people justifiably saw them as nothing more than violent plunderers. So if England was looking at sin, maybe they should start with that one.
It was all very disheartening, though, and very concerning. And even more ominous was the fact that in 1658, Cromwell died. And it was with that news that New Haven minister Hugh Davenport voiced an idea that other people couldn’t bring themselves to consider. It’s possible that we were wrong.
Davenport had never been fully convinced that the world was on the edge of the Millennium. He wasn’t fully convinced that it wasn’t, and he thought it was probably coming reasonably soon, but looking around and reading the Bible, he just couldn’t believe Cotton’s idea that it was coming today, or tomorrow, or within Cromwell’s lifetime. In the months following Cromwell’s death, Davenport offered his own interpretation. Charles Stuart would be restored to the English throne, and because Jesuits would be the ones who put him there, he’d bring Catholicism back to England. England would turn seriously against Puritanism, and then, who knows. Roger Williams thought Davenport might be right, but other New England and Puritan leadership rejected the thought. Even as Davenport assured people that at the end, righteousness would ultimately triumph, and that they should stay strong and wait, the implications were unthinkable.
And that’s where we’re going to leave it for today. Next episode, we’re going to look at the last years of Cromwell’s life, and the aftermath of his death, in Barbados, Virginia and Maryland.