Pirate Attack!

Rediscovering the epic battle off West Caicos.
By Ben Stubenberg

On an early summer morning in 1798, a balmy breeze filled the luffing sails of five sturdy sloops setting off in search of a ship that had run aground. From Ft. George Cay, the boats glided south along the white sand beaches of Pine Cay, their long booms reaching far over the turquoise water to catch the following wind and speed them along. The leader of the small flotilla, Loyalist planter Col. Thomas Brown of North Caicos, must have anticipated trouble for he loaded the boats with cannons and muskets. Then he did something seemingly counter to common sense, and not for the first time; he put those weapons in the hands of an all-Black crew of enslaved men. Brown’s hunch proved right, as pirates showed up in the afternoon off West Caicos, guns blazing and spoiling for a fight.

Local artist Richard McGhie painted this depiction of the battle between Thomas Brown and his crew and the pirates off West Caicos.

Launching a journey of rediscovery

Now, 223 years later on a summer afternoon in 2021, local Captain Ernesto Von Der Esch, Agile LeVin, Lynn Pelowski and I set out to find the spot of the long-ago battle. We admit to a juvenile thrill, once again imagining ourselves as pirates back in the day. Didn’t we all want to hoist the Jolly Roger and raid ships with cutlass in hand while living free on the high seas? Reality is somewhat different, we know. But on this day, we recaptured a bit of our childhood on our way to rediscovering the baddest pirate attack in Turks & Caicos history.

But Brown’s encounter with pirates was no ordinary swashbuckling adventure. The showdown off West Caicos brought to the fore a confluence of slavery, trust, bravado, foolhardiness and courage under fire, all against a backdrop of French and British forces clashing on the edge of empire for dominance of the Caribbean and the world.

Some 15 years before us, Providenciales veterinarian Mark Woodring came across a cannon and the remnants of a wreck off the eastern shore of West Caicos. He contacted a historian friend who recognized the spot as the possible scene of Brown and crew’s encounter with pirates. After reading my article, “Hidden Legacy: Slavery and Loyalists in ‘Grand Caicos’” (Times of the Islands, Spring 2020), which included Brown’s skirmish with pirates, Mark contacted me and generously provided the coordinates for follow-up.

The COVID-19 pandemic put a damper on plans for an expedition in 2020. Even after restrictions eased, we waited for the normally choppy seas on the windward eastern shore of West Caicos to abate to have the best shot of finding the cannon. Then we could place the battle with some confidence and game out the story of what probably happened. The summer winds blowing from the southeast didn’t let up, however, so on July 31, 2021 we decided to just go for it.

Heading to West Caicos

At Little Water Cay, the sloops cut through the Leeward Channel that led to the Caicos Banks while the tide was still high enough for the keels to clear the shallow bottom. The boats continued sailing downwind along Providenciales’ south coast past Long Bay, Gussy Cove, (now South Dock) and Five Cays Bay. From here they took a straight shot to Southwest Reef just off the south end of West Caicos and the wreck they hoped to find. The enslaved crew relished the chance to be on the water and away from field work on the plantations. But they also knew that pirates lurked off the coast and so steeled themselves to the prospect of an attack.

Just before noon, Brown and the crew ate pieces of johnnycake and knocked back a slug of rum, as was the custom then. Just ahead, they caught their first glimpse of the masts from the stranded merchant ship protruding above the reef. The name of the ship is lost to history, but it had sailed from the state of Rhode Island loaded with supplies the planters had ordered and badly wanted to recover.

This map of the Caicos Banks shows the route that Thomas Brown likely took to the pirate attack area off West Caicos.

I sat down with local mariner David Douglas who has sailed these waters for more than 35 years in his locally built schooner, the Atabeyra, (suncharters.tc) and asked him if this route made sense. “Yes, from Ft. George Cay, Brown most likely would have sailed south of Providenciales to get to Southwest Reef. The other alternative would be to sail across Grace Bay to Northwest Point. And from there cross the channel to West Caicos. That would have taken quite a bit longer and leave them much more exposed to pirates. So the southern route makes much more sense.”

Casting off from South Side Marina on Providenciales in Captain Ernesto’s boat MV Bonita (OceanFrontiersTCI.com), we followed Brown’s probable route heading to West Caicos. No doubt Brown and his crew would have stared in disbelief at the superbly comfortable and fast 37-foot fiberglass Axopar with two huge 300 hp outboard motors. As we closed in on Southwest Reef using the coordinates Mark had provided, Captain Ernesto cut the engines. Somewhere below lay the cannon. Agile, co-founder of  visittci.com and a font of TCI historical knowledge, prepped his underwater camera while Lynn began filming.

We took in the scene as our boat rocked in a sea awash with endless hues of blue and streaked with golden brown Sargassum seaweed reflecting off the mid- day sun. To the south, rows of cresting waves splashed over the shallow reefs that had claimed so many ships passing through. And further off lay the shore of West Caicos, a line of scrubby white bluffs mixed with sand and limestone stretching for miles without a trace of human presence. Unchanged over years, we could see what they saw and slipped for a moment back in time.

“Burntfoot” Brown’s defiance

Just who was Thomas Brown and what plight in his vastly different world brought him here? The man is no stranger to the pages of this magazine. Dr. Charlene Kozy’s four articles—“Hidden History” (Winter 2007/2008), “Revealing Thomas Brown” (Fall 2009), “All the King’s Men” (Fall 2010) and “The Rest of the Story” (Spring 2012)—provide illuminating portraits of the Loyalists in the Turks & Caicos and Brown in particular. As one of the most resilient, headstrong and paradoxical characters in TCI history, he warrants continued examination.

In 1775, just shy of his 25th birthday, Brown sailed from the bleak but prosperous North Sea town of Whitby, England to Georgia in the American Colonies. Thanks to financial help from his prominent father and contacts made in Savannah, he bought land to establish a cotton plantation in the back country near Augusta. But this was also the year that calls for independence from Britain reached a fever pitch that sharply divided the Colonists between Loyalists and Patriots. Brown had not been shy about declaring his Loyalist support for King George III.

In his book, The King’s Ranger, Edward J. Cashin describes a definitive moment in Brown’s life. One evening, a mob of 100 or so members of the fervent pro- independence group Sons of Liberty gathered in front of his house and demanded that he swear allegiance to the revolutionary cause. Brown tried to steer a noncommittal path, saying that he did not want to oppose the country of his birth, but nor did he want to offend those in his new home. But Sons of Liberty boys would hear none of it and closed in on him. Brown fired a pistol and fended them off with a saber until one of the mob smashed him over the head with the butt of a musket.

The Patriots then tied him to a tree, tarred and feathered him, partially scalped him and lit his feet on fire. Somehow, he survived, even after losing consciousness for two days. A doctor performed what passed for brain surgery in the 18th century to repair his fractured skull, but he would suffer severe headaches for the rest of his life. He also lost two toes in the fire, earning him the lifelong nickname “Burntfoot” Brown.

The bitterness from the attack, as well as Brown’s commitment to king and country, led him to join the King’s Rangers, a Loyalist unit of the British Army fighting George Washington’s men in the American South. He displayed remarkable courage and leadership in battle, often forging alliances with native Indian tribes and fighting alongside them. He may also have sought revenge.Legend has it that Brown hanged 13 captured American Patriots so he could gloat while watching them die.

Second chance in North Caicos

After the war, the victorious Patriots forced Brown and tens of thousands of other Loyalists out of the new American republic and confiscated the property they left behind. Most Loyalists from the American South fled to eastern Florida before taking refuge in the Bahamas. Some, like Brown, made their way to North Caicos where Britain compensated Loyalists for the loss of their plantations with land grants and money.

Brown soon became a successful cotton planter on North Caicos—made possible, of course, by the forced labor of men, women and children he had enslaved and brought with him. In what was then called “Grand Caicos,” Brown is said to have permitted slaves to cultivate small plots of land for themselves. On occasion, if one of those he had enslaved wanted to marry someone held in bondage at another plantation, he “bought” that person so they could be together.

Loyalist slaveholders, like their counterparts throughout the Caribbean and American South, portrayed their relations with the enslaved as paternalistic or benevolent to justify keeping them in oppressive bondage. Their narrative also served as an effort to offset growing abolitionist agitation to end slavery that Brown would be quite aware of.

We have no written accounts of what the enslaved on North Caicos thought about Brown’s “generosity.” We do, however, have a first hand account by formerly enslaved Mary Prince that details the horrific treatment meted out by Bermudian enslavers on Grand Turk. Though conditions differed for the enslaved on North Caicos who toiled in fields rather than salt ponds, shards of oral history handed down from generation to generation from the 1800s present a different version of Brown, who is remembered as a cruel slave holder. These two contradictory versions of Brown are not necessarily mutually exclusive, however, as he may have alternated between affection and abuse that characterized many slaveholders of the time.

Arming slaves

The story gets complicated because Brown did in fact develop a trust for many of those he had enslaved, contrary to the mindset of most plantation owners who had a well-founded fear of slave uprisings. Indeed, slave rebellions flared up throughout the Americas, but they were almost always quashed by colonial armies and local militias.

In the 1790s, the prospect of a successful revolt became terrifyingly real when slaves in the French colony of St. Domingue, now Haiti, rose up and beat back French forces and took control of wide swaths of territory. Stories of rebellion in Haiti also circulated widely among the slave population in TCI, just 90 miles (150 km) to the north, that would later inspire several successful slave escapes by boat. (See “Sailing to Freedom” in the Times of the Islands Winter 2018/2019 issue.)

For slaveholders living with these anxieties, proposals to arm slaves would be an anathema to their way of life. Nonetheless, exigencies arose that from time to time necessitated taking the risk of giving the enslaved weapons to fight a foreign enemy and protect the interests of the enslaver.

In the book Arming Slaves, historians Philip D. Morgan and Andrew Jackson O’Shaughnessy write, “The arming of slaves in the Americas was never part of a deliberate or concerted policy but rather was warily adopted as an urgent measure in response to a crisis.” They go on to write, “An inherent ambiguity therefore existed in colonial society between keeping firearms out of the hands of slaves and arming them whenever it seemed necessary or useful. Arming slaves was a dangerous expedient, but one resorted to frequently.”

A driving force for arming Blacks in the Caribbean was the high mortality rates of troops arriving from Europe compared to enslaved Africans. For example, the British lost more than 5,000 troops to disease during their occupation of Havana in 1762–63. During the American Revolutionary War, 11% of European soldiers bound for the Caribbean died on the troop transport ships. And once in the region, the annual mortality rate of soldiers was 15% compared to just 6% of those stationed in New York. Of the 1,008 men of the Seventy-Ninth Regiment stationed in Kingston, Jamaica in 1778, “Scarcely a man remained of the original number” 12 months later.

During the American Revolution, British military officers experimented with forming units drawn from slaves who escaped Patriot slaveholders. Loyalist slaveholders sharply disapproved, but British commanders held more sway. By 1782, near the end of the war, the British had more than 700 enslaved Blacks in uniform and under arms, along with thousands more in auxiliary positions, with the promise of freedom after the war.

Patriot slaveholders opposed the arming of the enslaved as fervently as their Loyalist counterparts. But the Patriots largely succeeded in preventing the recruitment of fighting units made up of slaves to serve the American Revolution. Nonetheless, many Blacks, some enslaved but most free, did serve honorably and proudly on the side of the Revolutionaries. Indeed, some of the enslaved on both sides had been warriors in Africa before being captured and sold into slavery and so adapted well to warfare.

At the end of the war, the British evacuated the slaves who had given them loyal service from the American colonies and deployed them to Jamaica and other Caribbean colonies as part of a larger West India Regiment. However, Britain reneged on the promise to free many of the slaves they had recruited, underscoring the continuing disagreement within British colonial society over slavery.

Brown almost certainly would have been familiar with the British arming slaves for military action during the American Revolution and may have seen first-hand their capabilities in combat. That may have imbued him with confidence that he could rely on enslaved men to defend TCI and serve him, as the need arose.

This summer, a crew of residents in the MV Bonita followed Thomas Brown’s possible route to West Caicos and searched for the cannon that may have been used in Brown’s skirmish with pirates.

Defending the Caicos Cays

Simultaneously in the 1790s, tensions between the British and French escalated into what became known as the “French Revolutionary Wars” for who would reign supreme. France in particular supplemented its navy in the Caribbean by recruiting private vessels and outright pirates as “force multipliers” to raid British ships and disrupt trade. The French “Commissions,” also known as “Letters of Marque,” gave the private and pirate vessels the status of “privateers,” a tacit pass to rampage, as long as they left French ships alone. All European powers and the United States played the same game. Using their thin veneer of legitimacy, many of these French pirates now sailing as privateers called on French-controlled ports along the north coast of Haiti to resupply before heading back out for raids.

With more enemy French ships now searching for British ships to sink or capture (as well as American merchant vessels that had resumed supplying British colonies), TCI became dangerously exposed. The Loyalists had good reason to believe the privateer pirates or even the French Navy might attack them at their most vulnerable spot—the deep water basin near what is now Fort George Cay. This was the only place where merchant ships could sail through a cut in the reef and anchor securely to offoad supplies for the North Caicos Loyalists.1

To protect this choke point, the Loyalists, with Brown taking a lead, built a small fort in 1795 (possibly earlier), naming it Fort Saint George. When finished, Brown probably made the case for arming TCI slaves as a defense force, most likely in response to a shortage of white soldiers. It is plausible that many of the Black soldiers may have been recruited from the North Caicos plantations. Thus the Loyalists apparently relied on the very people they had enslaved to protect them, their families and their property from an enemy attack. And they did this despite the ongoing slave revolt in Haiti.

1Merchant vessels could also sail through the shallower Caicos Bank to the south and unload cargo onto smaller skiffs in Five Cays or near Bellefield Landing in North Caicos. But the Loyalists did not deem these locations as worth defending with a fort.

Hierarchies of enslavement

Brown appears not to have been troubled by the contradictions of his actions. Instead, he seems to have possessed an unwavering confidence that he could inspire fealty among the enslaved he had armed. This begs the question, of course, of why armed slaves would stay loyal instead of using the weapons against the enslavers, especially if there was no promise of freedom.

In the Introduction to Arming Slaves, history professor David Brion Davis states, “For slaves, military duty offered a welcome escape from the misery of plantation labor. The allure of a promise of freedom also entailed upward mobility, dignity, prestige and a chance to prove one’s manhood and to receive awards that would impress one’s peers as well as white authorities.”

In the brutal, unforgiving world during Brown’s time, the enslaved leveraged and took advantage of cracks in the system of oppression to improve their lot. While a full-on slave revolt was at times a possibility, it also entailed a risk of failure, followed by more oppressive servitude or death. That risk had to be weighed against sporadic opportunities to gain privileges, status and capital, even if short of freedom. In fact, many enslavers dolled out concessions to split slave societies into hierarchies as a way to divide and conquer.

Brown, perhaps in part due to his experience in forming alliances with Indians on the American frontier, more capably straddled the gray space of bondage and “bondage with benefits” without having to actually free the people he had enslaved (with a few exceptions). He undoubtably calculated that by elevating the enslaved to the stature of armed soldiers he could create incentives for loyalty and discourage the impulse to revolt or escape.2

When Brown sailed in search of the ship that had run aground off West Caicos, he could easily have tapped a reservoir of enslaved men he may have trained and drilled at Fort Saint George and whom he could count on.

2Brown and the other Loyalists experienced few if any slave escapes largely because there was no place for them to safely flee. Only after 1804 when the Haitian Revolution succeeded and welcomed escaped slaves did the enslaved of TCI have a nearby sanctuary to which they could sail to freedom. In fact, there were so many TCI slaves escaping that enslavers eventually formed a local coast guard to discourage and capture them. But this possibility for escape was only available well after Brown’s 1802 departure from North Caicos.

Pirates on the horizon

Brown’s sloops reached the wreck around noon. He and the men were excited to see the goods still on board and largely undamaged. But they noticed the absence of crew members from the ship, even though the vessel appeared intact. Their fate, too, is lost to history. Brown and the men did not dwell on the mystery, for they had work to do.

Sometime in the early afternoon as the men unloaded the cargo onto the sloops, they spotted a single ship under full sail larger than their sloops rounding the southern shoulder of West Caicos. The ship may have flown a British or American flag to signal a friendly vessel, in an effort to lull the Loyalists into complacency. As the ship drew closer, however, they struck a French enemy flag flying atop the mast, forcing an urgent decision:  Sail away with the supplies recovered or take on the pirates and maybe keep salvaging what was left on the wreck.

Brown implored the Loyalists in the other boats to stick together and fight, arguing that their five boats could take on one pirate ship. The Loyalists shouted back that they had no chance and called for Brown to make haste and leave with what he had. Brown staunchly refused. Revealing the limits of Brown’s clout, the other Loyalists trimmed the sails of their four sloops and tacked back toward Providenciales. That left Brown, ever the fighter, to face the pirates alone with his crew.

The enslaved men in Brown’s boat, seeing the odds stacked against them, also tried to persuade him to flee with the others. Brown wouldn’t budge, though, and ordered them to ready for battle. At this point the enslaved may have considered the option of commandeering the sloop and escaping, which would have been easy enough. But they understood too that there was really no place to go where they didn’t risk death by exposure or capture and far harsher re-enslavement. So the enslaved unlucky enough to be in Brown’s sloop had little choice but to put their confidence in Brown’s blustery bravado in hopes they could survive as the pirates closed in on them.

Though fatigued from sailing most of the day and moving heavy cargo in the heat of summer, Brown and the men rallied. Adrenaline pumped through their veins as they rammed gunpowder and ball tight into their cannon. They loaded their muskets, careful to keep the powder dry. In the excitement, Brown called for his men to stay steady, just as he had with his troops back in Georgia two decades earlier when fighting the American Patriots. Hearts pounding and fortified with another slug of rum, they faced down the French pirates together.

As the pirate ship drew closer, Brown and the crew could see it had as many as 10 cannons, all bigger than theirs. The pirate ship fired the first cannon volley. Artillery back then had little accuracy, especially when fired from a ship, so the cannon ball splashed harmlessly away from the boat. Brown fired back to let them know he wasn’t about to retreat. But his cannon ball fell well short of the pirate ship, making plainly clear the pirate ship’s greater range.

Brown hoped that his more maneuverable sloop would have a chance of getting close enough to the pirate ship to kill or maim at least enough of the crew with his smaller cannon and muskets, even if he could not actually sink the ship. Brown surely attempted, but the pirate ship kept just out of range. Each time Brown approached closer to the pirate ship, he only increased the accuracy of the pirate cannons. Tacking back and forth over the choppy sea, the two ships dueled with cannons and muskets, trying to get in the one shot that would count.

In the late afternoon, a pirate cannon ball finally smashed into Brown’s sloop, injuring two of the men, though not mortally. Water rushed in and the game was up. Brown and the men strived to stay afloat in the choppy sea as they made their way toward the West Caicos shore they could see in the distance.

Article author Ben Stubenberg freedives to the cannon found by following Mark Woodring’s coordinates off West Caicos. Note the large field of ballast stones appearing in the shape of a boat at the top of the photo.

Finding the cannon

We only have two contemporary accounts of the battle. The first is a letter from Brown to his father in Whitby dated August 8, 1798 in which he cites the clash and says that he was so proud of his men that he did not mind the loss of his goods.

The second is a publication in the Bahamas Gazette on August 21, 1798 that Professor Cashin summarizes in The King’s Ranger:

“A ship bound for Grand Caicos was wrecked on nearby West Caicos. Brown and other planters sent their boats to retrieve goods belonging to them. As the supplies were being transferred into the small boats, a French privateer came up under full sail. Four vessels made a run for it, but Brown’s men decided to fight for possession of the wrecked ship. The all-Black crew was armed with only a two-pounder cannon and muskets, but they drove off the French repeatedly. The heavier armed privateer stayed out of range of Brown’s defenders and used its cannon to sink Brown’s boat. The valiant crew swam to shore.3

Based on these contemporary accounts, the fluid nature of slavery, and descriptions of boats, pirates and cannons of the time—all seasoned with a dash of imagination—a narrative can be created, as I have done. But more concrete evidence could help confirm the setting. For that we had to jump in and see the cannon for ourselves.

In the rolling sea just a few yards from the Bonita anchor line, we noticed a dark patch surrounded by sand. Agile and I put on our dive masks and fins to get a better look. Within minutes Agile cried out, “I found it!” And sure enough, 10 feet (3 meters) below the surface in water as clear as a window pane, the rough shape of a cannon appeared covered in sponges and sea plants. Mark’s coordinates were spot-on.

Captain Ernesto leaped in as well, and the three of us took turns free diving down to take pictures and measure the cannon’s length and muzzle width to determine what we had. Lynn rolled the video and took photos from the boat as we barely contained our excitement. A tape measure showed the cannon to be about 5 feet (1.5 m) in length (adjusted for marine vegetation) with a 3.5 inch (9 cm) muzzle, which would be consistent with a six-pounder. But just whose cannon did we find? The six-pounder (based on the weight of the projectile it fired) could have fit on Brown’s sloop, but the Gazette letter and Professor Cashin’s summary noted a much smaller two-pounder.

Right next to the cannon, a large field of ballast stones appeared in the shape of a boat that looked to be about 40 feet long and at least 15 feet wide. That would have been just big enough to be a small ocean-going vessel, but could also have been a large local sloop. The stones themselves, however, were granite, which would probably not have been used in local TCI sloops since this type of rock is not found here. Could the cannon and remnants be from the Rhode Island vessel with the supplies Brown and his men wanted to recover?

It’s not clear what sank this boat. The cannon and remnants of the wreck were about 1/2 mile (800 m) from the reef, well past the narrow channel off the southern end of West Caicos that ships used for transit. It might have hit a coral head that ripped a gash in the hull, causing it to take in water. Or the ship may simply have gotten stuck in the sand on a shallow bank. In either case, the deck could have been above the waterline, thus preserving the cargo for salvage. The waters around TCI are replete with ships wrecking on the reef or a sandbar, some visible above the surface today.

A more intriguing possibility is that the vessel was sunk by pirates who left the boat half submerged as bait for the salvage sloops sure to come looking for it, as in fact happened. If the pirates anchored their boat on the calmer lee (west) side of West Caicos, they could remain hidden. Then from the hills on West Caicos, the pirates would have a good vantage point to see any boats heading from the Caicos Bank south of Providenciales and prepare to attack them.

Professor Cashin’s summary and the original Gazette report stated that the men swam to shore after the boat sank, but it’s not clear where they ended up. As an open water swimmer in TCI, I am familiar with the currents around the Islands and the challenges they present. From where we found the cannon, the shore of West Caicos is about 2 miles (3.2 km) away. Swimming that distance requires some training, something we can be fairly sure Brown and his men didn’t have, even if they knew how to swim. Moreover, they would have been fatigued from unloading supplies followed by an afternoon gun battle. 

However, from our spot, a strong southeast to northwest current pushed the water towards the eastern shore of West Caicos. So assuming the pirates sank Brown’s sloop in the vicinity of the wreck we found, it is quite possible the men made it to the beach this far out without actually having to swim the whole way. If they clung to something floatable, they could have just drifted to the shore. Had Brown’s boat been sunk in any other location off West Caicos close to a reef, such as off the north tip of the island, he and the crew would have likely been swept out to sea.

To be sure, the assessments made are far from conclusive. The contemporary accounts of the attack, even with questionable descriptions and crucial omissions, at least confirm a battle with pirates off West Caicos. We don’t know if the cannon and remnants of the wreck we found were from the Rhode Island vessel the Loyalists salvaged. However, the location and size of the ship based on ballast stones suggest that possibility. When taken together with the prevailing current that Brown and his men would have relied on to get to shore after their sloop was sunk, a plausible case can be made that the windward side of West Caicos was the scene of the battle.

We need to go back to collect additional evidence from this cannon and wreck, as well as do a larger search of the area for other cannons and wreckages. If we are lucky enough to find Brown’s sloop and cannon, we could make the case with a high level of confidence.

3Professor Cashin’s quoted summary differs a bit from the actual article in the Gazette that relies on an unsourced “Letter from Grand Caicos.” The Gazette recounts the pirate attack on the Loyalist sloops near West Caicos, but the battle descriptions are questionable and the story is incomplete. I’m using Professor Cashin’s summary that gives a clearer picture.

Questions for Brown from the 21st century

Let’s start by asking what in the world propelled Brown to risk his life to take on the pirates just to secure a few more supplies from the Rhode Island wreck? If he only carried a couple of two-pounder cannons, he had almost no chance of succeeding against a ship with bigger guns with more range. Even if he had a larger six-pounder cannon (which seems more likely if he truly believed he might encounter pirates), he still would have been at a significant disadvantage. Perhaps he wanted to relive the thrill of battle again, a hero who refuses to turn and run, even though he had nothing to prove. Or maybe he really did think he could get off the crucial shot that would cause the pirates to cut and run—though foolhardy, as the outcome shows. He could have escaped with honor and most supplies to fight another day.

What happened after Brown and the enslaved men were stranded on West Caicos, and how were they rescued? That is itself a compelling story. How long did they go without food or water? Did the other Loyalists return to get them even though it could have entailed another confrontation with pirates? If so, was Brown grateful or did he chastise his Loyalist rescuers with sharp words for fleeing when he stayed to fight?

What of the ship from Rhode Island? How did the Loyalists get word that it had wrecked? If the ship’s supplies were intended for the North Caicos Loyalists, why was it attempting to negotiate the narrow passage between Southwest Reef and the southeast coast of West Caicos instead of sailing to Fort Saint George? Perhaps it was trying to reach the Caicos Banks and Gussy’s Cove on Providenciales, but clearly something went terribly wrong. Perhaps it was a navigation error, perhaps a storm, perhaps a cannon ball from pirates. But if the ship was in fact intending to deliver supplies in Providenciales, that would call into question who really owned the supplies on the ship.

Finally, what happened to the pirate ship that had sunk Brown’s sloop? Did the pirate ship launch smaller tenders armed with cannons to chase down Brown along the reef over shallow water? Did it try to recover the supplies still on the wreck? After a lengthy battle and taking some risk, the pirates would probably want to recover some booty for their efforts rather than just sail away.

Brown’s choice

Most noteworthy is the undaunted courage of the men in battle, as indicated in Brown’s prideful letter to his father and the Gazette account. The crew may even have saved Brown after his imprudent brawl with the better armed pirates, though they surely fought to survive and save themselves first.

In an astonishing twist of irony, the pirate ship they encountered may well have included escaped slaves. Indeed, former slaves sometimes made up as much as 1/4 of a pirate ship’s crew. On board, these men instantly went from bondage to liberation with the same claim to a share of the booty and a vote in the election of the ship’s captain as the rest of the crew. Many pirate ships practiced this early form of democracy decades before citizens of imperial regimes acquired anything resembling equal rights.

It is entirely possible that Brown’s crew, caught up in his reckless showdown, were in fact battling free men who were recently enslaved like them. On occasion, pirates of the Caribbean would deliberately put Black pirates prominently on deck brandishing weapons to intimidate merchant vessels they intended to attack. If the pirates attacking Brown’s sloops did this, they they could have been quite visible to Brown’s Black crew in the course of battle. We’ll never know if they actually saw each other or if they reflected on their respective fates in the moment. But it is fascinating to speculate, as it adds another layer to the tangled, intriguing history of our Islands.

Though Brown clearly admired his men’s performance, he still could not muster the courage to see them as fellow human beings deserving of freedom. Standing shoulder to shoulder as cannon and musket balls and grape shot whizzed past their heads was not enough to crack Brown’s conviction that the men risking their lives for him were still his property. And that is the saddest part of this tale.

Thanks to influential contacts in England, Brown would be granted a large tract of fertile land on St. Vincent to cultivate sugar cane. In 1802 he began moving those he had enslaved (he says 623, but I believe that number to be vastly overstated) from North Caicos to St. Vincent. “Black Caribs,” a cultural and racial mix of Carib Indians and shipwrecked slaves from Africa, already inhabited the land Brown had been granted. But that is another story for another time. Suffice to say that the Black Carib values of acceptance and integration were lost on the planters who took over. Brown died there in 1825 at the age of 75 without freeing any of those he had enslaved, except maybe for one or two who may have been his offspring, which itself is telling.

History passes judgment on how we handle the challenges handed us by fate. But the light glares more harshly on those with means and privilege because they have the power to change the lives of those who have none. In the end, Brown is both hero and anti-hero of his own story. His audacious bravery, force of character and defiance of convention remain undisputed. But on that searing summer afternoon off West Caicos, when the enslaved men in the stout sloop stood tall for Brown, he chose to keep them captive. And for that he must be held to account, even centuries later.

Ben Stubenberg (bluewaterben@gmail.com) is a contributing writer to Times of the Islands and a popular story teller about pirates in TCI. He is the co-founder of the TCI swim and tour adventure company, Caicu Naniki, and the annual “Race for the Conch” Eco-SeaSwim.

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South Caicos was once a major exporter of salt harvested from its extensive salinas. Award-winning Master and Craftsman Photographer James Roy of Paradise Photography (myparadisephoto.com) created this vertical composition by assembling a series of six images captured by a high-definition drone which was a half a mile away from his position.

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  • Landscape
KR LogisticsSWA
jsjohnsonDempsey and Company
Hugh ONeillTwa Marcela Wolf
Parkway Pest SolutionsJohn Redmond
Misick & Stanbrook Caicos Express Air
Island Escapes TCILandfall
Great Bone Fishing Race for the Conch


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