Empire of Liberty: The American Caribbean

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“Many consider these fair waters to be little more than the source of wealth. They would be wise to consider them a gateway and crossroads of Europe, Africa and both Americas. If the Levant is the key to the Old World; the Caribbean is the key to the new.” 

~ William Briggs

Excerpt from Douglas Oswald’s “Annotated History of the American Revolution”, University of Michigan Press, 1932.

At the onset of the revolution, the legal status of much of the British Caribbean was suddenly thrown into considerable doubt. Before the war these royal colonies were a hodgepodge of tropical outposts designed to gather resources (normally sugar but sometimes coffee or tropical lumbers) and counter French, Dutch or Spanish ambitions in the region. For example the majority of British commerce centered on the incredibly profitable sugar plantations of the Lesser Antilles Islands and Jamaica. British outposts off the coast of Central America gathered lumber and hindered the Spanish. The Cayman Islands and the Bahamas were good strategic outposts but their sandy islets and shallow cays prevented the dominant sugar economy from, quite literally, taking root.

In addition, the nature of the Caribbean meant that control of the islands themselves was tenuous at best. Many islands were swapped back and forth between Britain and other European powers during the constant outbreak of wars that occurred from the 16th century until the American Revolution. Several islands (Dominica, Grenada, and St. Vincent) were eager to join the American cause as they had been recently conquered during the French and Indian War and had sympathetic French populations. In addition, the Caribbean islands were especially vulnerable to slave uprisings, disease, hurricanes, and piracy, which made their situations extremely unstable. This led to a continuous parade of colonial governors sent from London and constant reorganizations in an attempt to manage the ever changing mess. At the time of the Revolution, the Cayman Islands and British holdings and protectorates in Central America were administered from Jamaica. St. Vincent and Grenada had equally fair claims to the smaller Grenadines Islands such as Petit Martinique and Bequia. Anguilla was administered from Antigua and Antigua itself was administered as part of the British Leeward Islands which itself was divided into northern and southern groupings.

Lastly, by the time of the Revolution the settled white population of townsfolk, overseers, and resident plantation owners were at odds with incompetent colonial administrators and landowners who were happy to manage their estates from Britain via proxies. This cultural divide combined with the uncertainty of the situation on the American Main to make the Caribbean ripe for joining the revolutionary cause which is exactly what happened over the course of 1775 and 1776. Simply put, the pent up animosity and potential for economic gain by keeping profits at home, instead of shipping them back to Britain, outweighed the tenuous strategic position of the various islands allowing rebellion to foment.

Of course the rebellions were complex affairs for many reasons, strategic and social.

While the middle and lower classes of white Britons supported the revolution, the powerful estate owners who actually did reside in the Caribbean found themselves divided. Many landowners maintained deep connections to the homeland, both aristocratic and economic. Others harbored revolutionary sentiments for the antithesis of those very aristocratic and economic reasons. Not a few plantation owners’ families originally immigrated to the Caribbean as a way of establishing fortunes which would allow them access to royal society back in Britain. As the noble class is difficult to break into by design, more often than not this failed to occur. Perhaps the most likely reason for a plantation owner to split with Britain and join the revolutionary cause was money, or lack thereof. Plantation maintenance was a costly affair and even costlier were the expenses incurred to maintain a family’s social atmosphere. Like their mainland plantation brethren, many Caribbean planters found themselves deeply indebted not due to operating costs but rather the constant importation of furniture, manufactured goods, fashionable clothing, books and other items which indicated status above the middle and lower classes. Naturally such social jockeying tended to stratify the classes and put them at odds with one another, though a calcified caste system as existed in the French and Spanish colonies never took complete hold of British island society.

This is not to say that a caste system didn’t exist at all for one certainly existed amongst the races. Most islands featured massive African slave populations. Unlike their counterparts on the American Main, these slave populations never truly established self-sustaining native populations. Disease and nightmarish working conditions ensured high mortality rates thus requiring a constant “resupply” streaming across the Atlantic via the slave trade (which harbored just as horrifying mortality rates and inhumane conditions). The complete ratio imbalance of whites to blacks created a constant fear of a slave revolt. That the islands joined the revolution at all is a bit of miracle considering this factor alone. Any white rebellion could spark a black rebellion and all parties, slave and free, colonial and royal, were keenly aware of that fact.

This mentions nothing of the “castes” between whites and blacks. A mixed race class of mullatos also existed and their legal reality was complex to say the least. Darker skinned mullatos would often be lumped in with the black slave population while, sometimes, lighter skinned mullatos usually met enslavement but were spared the worst labor. Often, the position and slave status of the mixed race child of a white male and a black female would be determined by the white father but this also depended on the father’s social rank and sometimes, judges or citizen’s councils. The system was ad hoc to say the least but the only consistent factor was its brutal protectionism of the slave system and the assurance of white superiority at the top of the social pyramid. Lost in the hierarchy were those who chose to live outside of it. Remnant Carib indian populations existed throughout the Caribbean, mainly in isolated jungles and montane areas. The most notable example of this occurred on St. Vincent. Recently captured by the British in the wake of the French and Indian War, the new British overlords learned that the French had done little to eliminate Carib resistance and that the tribes mostly dominated the interior mountains and windward side of the island. The Anglo-Carib War began in 1769 and ended in 1773 in a stalemate. A peace treaty split the island into two portions with Anglo-French settlers controlling the south and leeward side and Caribs controlling the north and windward side. Escaped slaves, typically referred to as maroons, inhabited similar environments. The most notable example of a resistive maroon community were those maroons who inhabited the Blue Mountains of interior Jamaica. These communities were originally founded by escaped Spanish slaves (before the British take over of Jamaica) who combined with refugee Taino indian tribes. As in St. Vincent, a 1731 Anglo-Maroon War yielded inconclusive results and in 1740, a treaty allowed a tense armistice.

Thus, when the revolution spread to the Caribbean the same questions about liberty and humanity that plagued the southern mainland bubbled to the fore. Just as Thomas Jefferson struggled with the concept that “all men are created equal” despite his own ownership of slaves, many Jamaicans, Barbadians and Antiguans would grapple with the same philosophic hypocrisy. They never reached a conclusion. Like many early Americans they were content to allow the hypocrisy to stand in their whip hand while they pursued enlightenment philosophies and revolution with the other.

Naturally London considered the Caribbean rebellion would be the easiest to put down. The social disorder sewn by rebellion ensured they would have a loyalist population to draw from and, if not, they could always drop a match into the slave powderkeg. The powerful Royal Navy scoffed at the mere possibility that these strategically isolated islands could stand up to their sheer might. As Admiral Samuel Hood, Commander-in-Chief of the Leeward Islands Station (based at English Harbor, Antigua), stated when the first rebellions occurred in 1775:

“It would take all of the navies of Europe, all of the pirates of Tortuga and Malacca, and every sunken ship and drowned sailor from today to Salamis, combined, under the command of Drake himself to hold us back from reclaiming these islands from the rebels.”

Hood would have been wise to heed the lessons of the superior Persians at the very battle he referenced.

The legend of Commodore William Briggs begins in 1775 when he quickly rose to prominence from a drunken, if inspired, royal navy officer to a charismatic revolutionary commander.  His low birth preventing him from upward advancement in the navy, he opted to listen closer to the whispers of lawyers and merchants in the taverns around the Caribbean as his ship made patrol rounds. Boldly offering his services as a naval officer to a group at Spanish Town one evening, casual discussion over rum evolved into full fledged plots of rebellion [1]. Five days later, Briggs organized a massive sailors revolt in Kingston Harbor (a testament to Briggs’ leadership that the Crown missed out on) and sparked the revolution. By the time the revolt ended, Briggs and his rebels had captured Kingston, Spanish Town, what was left of Port Royal and 31 ships in Cagway Bay [2]. In a further testament to Briggs’ ability, grassroots rebellions (spurred by his personal efforts) sparked seemingly all at once in Nassau, George Town, Bridgetown, Plymouth and English Harbor [3]. That last rebellion at the anchorage of the Royal Navy’s Leeward Island Station sent the arrogant Admiral Hood reeling in five ships to Bermuda; Briggs’ captured 49 ships that day (mostly merchants but several powerful ships-of-the-line).

How a little known officer with origins in Yorkshire transformed himself seemingly overnight into a consummate patriot, a respected leader and an idolized revolutionary has been subject to over a century of debate.

Firstly, we must remember that in his time Briggs was one of many respected Caribbean leaders and hardly fostered a multi-island revolution with his bare hands. Instead he was joined by prominent lawyers, merchants and landowners. Henry Black became a symbol of Leeward Island politics for decades, even if his appointment to the Second Continental Congress is a mystery. Malcolm Atwell, a prominent merchant from Barbados who specialized in the tropical hardwood trade, stirred rebellion in Bridgetown. Even the sudden revolt in Jamaica was largely planned and orchestrated by the sudden turn of Gov. John Dalling. Like his Quebecois counterpart, Guy Carleton, somewhere just before the revolution it appears the two royal governors “went native” and were willing to throw off their oaths and prior loyalties in favor of the revolution.

Secondly, Briggs became something of a symbolic figure over his long naval and political career in a way that Dalling or Atwell never matched. Not only did this symbolism stem from his astounding victory at the Windward Passage but also later naval victories in this war and others, his achievement of the Vice Presidency, and his prominent role in the Haitian Question. Through the years he had a tumultuous relationship with the Caribbean but his longterm legacy is one of legend.

Thirdly, and finally, one must simply relent to the man’s unimaginable sense of charisma and energy. Like so many of America’s great leaders, Briggs had the ability to inspire crowds of men to action with merely a few words. His tactical ability is astounding in his ability to consistently outfox and out-maneuver the Royal Navy across the Caribbean. In the nascent days of the Caribbean revolts he often our-raced the news of his own revolts from one island to the next. His ambush at the Windward Passage is strategic genius bordering on pure dumb luck. Napoleon’s marshals often spoke of L’Empereur’s ability to predict enemy movements and accurately pinpoint battlefields weeks in advance as if they superpowers. Briggs’ officers through the years would frequently make similar commentary.

His legend cemented at the Battle of the Windward Passage, the legal complexities of the region continued to unfold.

At first, as the islands began to throw off colonial yokes, they organized based on territory. The Second Continental Congress saw delegations arrive from the individual islands themselves. The only British North American territories not represented in Philadelphia were the Central American outposts, East and West Florida, Tobago, Bermuda and the vast Hudson’s Bay Company holdings in Canada. The delegations to the Congress actually worked together quite well even if the authority they acted upon was questionable. Many of the smaller islands had unique free populations, all dwarfed by massive slave populations, and only a handful had pre-established colonial assemblies. Many islands had to create assemblies from scratch to vote on delegates. Sometimes this occurred with the actual formation of a new assembly as was the case in St. Christopher [4] and the Bahamas. On the smaller islands the assembly was little more than a majority of free landowners meeting at a church. As mentioned earlier, Henry Black claimed to be the delegate from Anguilla despite there being no record of any colonial assembly, or any meeting, at all. Luckily for Black, the self-appointed delegate proved so competent at his duties the voters of Anguilla opted to officially vote him into whatever office he opted to run for until he died.

Despite the results at the Windward Passage, the Crown was not yet ready to cede the valuable islands without further attempts. Rodney’s defeat was humiliating and the Admiralty assigned him to handle naval matters along the American Main. In turn, they opted to give Admiral Hood, himself humiliated after having had to flee the revolt at English Harbor and barely escaping court martial, a chance at redemption. Hood gathered a fleet at occupied-Nassau in late 1778 and opted for what he deemed an “island hopping campaign” across the valuable Windward Islands of Dominica, Grenada, St. Vincent and Barbados. His hope was to draw Briggs away from Jamaica long enough for Admiral Samuel Barrington to sweep down from Bermuda and capture that invaluable jewel. Even if he failed, it meant the Crown would retake incredibly profitable islands and have a springboard for an invasion of the less profitable (but still important) Leewards. Perhaps most importantly, with rumors of France joining the war, Hood wanted to make sure that Britain retained those formerly French colonies and they did not use the revolution as a means to rejoin France in a few years. Of course, Hood was not alone in his thinking. Louis XVI was never shy about the hope that some former colonies might come back into the fold. Indeed, several leading politicians, including John Adams, doubted the patriotic loyalties of several islands that had only recently become British. In a famous spat while the Congress executed its work under great stress while exiled in Fredrick, Henry Perdue of Dominica called Roger Sherman of Connecticut an adulterer to which he retorted that Perdue was nothing more than a “French parasite”. The later Dominica Crisis bares further proof of these thoughts.

To Hood’s credit, his combined assault with Barrington worked. Briggs, despite his talents, could not be everywhere at once. Hood’s fleet occupied Barbados, Grenada and St. Vincent with little opposition from late 1777 through the spring of 1778. These occupations interrupted the creation of a combined “Windward Island state” that might better organize in its fight against the Crown. It did, interestingly enough, expedite the creation of a “Leeward Islands state” that merged Antigua, Barbuda, Anguilla, Montserrat, St. Christoper and Nevis in the summer of that same year. Confusingly for students of American history, St. Christopher and Nevis would later secede from the Leeward Islands during the Civil War, opting to form their own neutral state which remains separate to this day. There is no indication on record that these Royal military operations influenced the decision for the Cayman Islands and Jamaica to formally merge with the Caymans becoming a county of Jamaica. Sporadic attempts to convince British interests in Central America (a quasi-colony of loggers along the Yucatan, tenous control of the Bay Islands, and a protectorate and trading outpost with the Miskito indians) to join Jamaica or the revolution never went anywhere. These attempts at diplomacy ended when it became apparent that Spanish involvement in the war hinged on their ability to retake those regions and reattach them to the Spanish Main. The legal complexities and territorial jostling, even in the middle of a war, are an ironic testament to the complex colonial structure the British were forced to create over the years to maintain their own control up to the point of the American Revolution.

While Hood island hopped across the Windwards, Barrington sailed for Jamaica. To the surprise of Barrington’s captains and subordinates he ordered his invasion fleet northeast out of Bermuda. Only Barrington’s closest advisers knew his convoluted route, created with the sole intention of throwing off the one decent fleet the rebels maintained. Royal Naval intelligence informed the Admiral that Briggs’ fleet anchored not at Cagway Bay, but Montego Bay on the northern shore of Jamaica. This allowed Briggs to quickly sail towards whichever passage the Royal Navy opted to pursue (Yucatan, Windward or south of Hispaniola)…but it didn’t allow him much flexibility if the British sailed straight up into Cagway Bay…

Several weeks after departing Bermuda and porting at the friendly Azores the crews of the fleet prepared to sail past the sandy spits of land known at Bajo Nuevo Bank [5]. They were only a few days sail from Jamaica. As the early dawn lit the sea their eyes widened as they beheld, in shock, Briggs’ fleet, assembled in battle lines, ready to take full advantage of the shallow banks, and they even had the wind.

The April 21, 1778 Battle of Bajo Nuevo fails to live up to the luster of Windward Passage for many reasons, but it does not negate the strategic victory for the continentals. Caught flat footed, Barrington made a valiant effort to organize and put up a fight but Briggs’ ships held the advantage from the start. Barrington lost two frigates and an unknown fire devastated Barrington’s own flagship (sowing confusion amongst the British fleet) with several other vessels taking damage. With no safe ports nearby (and believing his fleet to be infiltrated by spies), Barrington opted for caution and made for occupied-Grenada. Briggs’ lost a brigantine, and his own flagship took some damage, but the casualties for both sides were light. Briggs’ could have pursued but refused to risk an encounter with his fleet against a combined Hood-Barrington fleet.

This gives rise to the obvious question: surely Briggs knew that Hood and Barrington’s fleets would combine regardless?

The answer is yes, but neither Hood, nor Barrington, knew that Admirals Charles Henri Hector, Comte  d’Estaing, Toussaint-Guillaume Picquet de la Motte, Luc Urbain de Bouëxic, comte de Guichen, and François Joseph Paul de Grasse had all entered the Caribbean basin. If Hood and Barrington expected to combine two fleets and take on Briggs together they would instead find that Briggs had merged his fleet with four French squadrons in turn.

For while Barrington took the long way around to Jamaica, and Hood picked off isolated islands, Paris had entered the war…

———-Author’s Notes———-

[1]: This was in the days when Spanish Town, not Kingston, was the administrative capital of Jamaica.

[2]: This does not imply that the revolt destroyed Port Royal. Instead, Port Royal had been destroyed in 1692 by an earthquake and tsunami and, like our timeline, it never recovered and the development in Jamaica shifted to Spanish Town and Kingston where it remains.

[3]: The author does not know this but these rebellions are the obvious behind the scenes work of the Order of Freedom.

[4]: St. Christopher being the old name for modern day St. Kitts.

[5]: Bajo Nuevo, Seranilla and Navassa are tiny Caribbean islets that are sometimes referred to as the “guano islands” dating back to a mid-19th century economic craze around the importation of guano for its use in manufacturing gunpowder or as a fertilizer. They are often combined with equally tiny reefs and islets in the Pacific that were prized for their guano and later strategic value as landing strips and fueling stations.

Next Chapter: The World at War

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