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Scottish Highlanders at Fort Amelia & the War of Jenkins’ Ear

February 25, 2025

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by J.P. Hackney (left) and John Steinmeyer of the Independent Highland Company of Darien. Photo courtesy of Mr. Hackney.

By Peter Hill

Old Town, Fernandina abounds in pirate lore. However, there is another group of romanticized, cultural outliers who also color its history. Fans of the television series Outlander might be surprised to learn that from 1736-1742 Amelia Island hosted a contingent of Scottish Highlanders. Whether any in their clan looked like the show’s hunky character, Jamie Fraser, or given the state of 18th century hygiene and dentistry, more like Pirates of the Caribbean, is unknown. What is known is that they spoke Gaelic and wore Highland dress, and as such were outliers in America just as they were back home were Lowland Scots called them the “Irish.”

James Oglethorpe, the founder of Georgia in 1732, stationed Highlanders at Fort Amelia, one of a half dozen forts used as buffers for his fragile new colony against the Spanish, just as his king wanted Georgia as a buffer for South Carolina which had grown rich through the exploitation of enslaved, African labor. Oglethorpe was given not only a royal charter, but the king’s blessing for Oglethorpe’s social experiment that envisioned Georgia as a home for debtors where rum, lawyers, Catholics, and slavery were outlawed! Knowing that on Amelia Island he was trespassing on Spanish territory, Oglethorpe reached an arrangement directly with Spanish officials in St. Augustine, where, in exchange for withdrawing British forces stationed still further south on the St. John’s River, the British would occupy the bluffs of present-day Old Town unmolested by the Spanish or their Yamasee Indian allies.


Map courtesy of Larry Ivers’ book “British Drums on the southern Frontier”.

Oglethorpe named the island Amelia in honor of British Princess Amelia, Sophia, Elenore of Hanover, beloved daughter of King George II of Great Britain, hoping George would be thus unwilling to ever return it to Spain. Spain, still recovering from the devastating War of The Spanish Succession from 1701-1715, tolerated the British presence on Amelia Island despite royal objection to the deal. Local reasoning was that in Spain’s weakened condition, “Guale” the vast, watery region between “La Florida” and South Carolina, wasn’t worth going to war over; not yet anyway.

The Highlanders had come from Inverness, Scotland and founded a town on the Altamaha River in 1736. Originally called New Inverness, the name of the town soon changed to Darien in recognition of Scotland’s failed attempt to build a colony by that name in Panama at the end of the previous century. Known as the Darien scheme, the colony failed miserably, and many of Scotland’s wealthiest families lost their fortunes funding the misadventure.


Largely as a result of the failure of the colony, along with the copious amounts of English gold used as bribes, the Scottish Parliament in Edinburgh voted itself out of existence through an Act of Union with England in 1707. This act relinquished Scotland’s sovereignty so hard won by Scottish heroes like William Wallace (Braveheart) and King Robert the Bruce. This still rankles independence mined Scots to this day, nor was it a happy marriage then; thousands of 18th Century Highlanders died in “risings’ against various British kings in London over the years.

Induced to leave Scotland by these ongoing troubles, a Committee of Trustees paid the Highlanders’ passage to Georgia in 1736. The cost of their passage was to be repaid by their indentured servitude, in their case military service, and as such they formed the Independent Highland Company of Darien that defended Georgia’s borders against French encroachment from Louisiana and the Spanish based in Florida. Highland men indeed wore kilts that they found easiest in which to run and fight. Warriors could never get “caught with their pants down” if they were not wearing any! However, women wore an arisaid, a modest, wrap around garment providing warmth should circumstances necessitate sleeping out of doors, and in a style brought to Britain by the Romans, single pieces of leather strapped to their feet! Though considered a “dead charge” by the Trustees back in London, if men were away women stoutly defended their homes and families against attacks.



Julie wearing a full body arisaid reenacts the role of an official wife of a soldier in Fraser’s Highlanders, a regiment recruited in 1775 to fight in the War of American Independence. Photo courtesy of Peter Hill.

Paraphrasing J.P. Hackney, an Independent Highland Company of Darien reenactor and amateur historian consulted for this post, Amelia’s fort (see the map from British Drums on the Southern Frontier by Larry Ivers shown above) was constructed by English militia men who had withdrawn from Fort Saint George on the north bank of the Saint John’s River. It was a simple fortification consisting of a large clapboard house with a stockade, a fence on top of earth works. In October of 1736, the Scots were still busy constructing New Inverness. Since many had brought families with them, there was domestic pressure to get that situation settled first. By 1739 Highlanders were occupying Fort Amelia in regular rotation. Oglethorpe liked rotating his people, and by then he also had a full regiment of Redcoats under his command. Garrisoning Fort Amelia were sixteen Highland Indentured servants who belonged to the Trustees, a Sergeant’s guard of twelve men from the Forty Second Regiment of Foot, and about ten women and children. There were approximately five cannons at the fort. A road to the south accessed a small guard house overlooking Nassau Sound. Life was good.



Reenactors from Oglethorpe’s Forty Second Regiment of Foot. Photo courtesy of Mr. Hackney.

On 13 November 1739, while gathering wood outside the fort, two Highlanders, John Mackay and Angus Macleod, were killed by Spanish soldiers and Yamasee warriors in what was the opening act in the American theater of a major conflict between Britain & Spain. Though later given a farcical name, the War of Jenkins’ Ear proved to be a deadly serious affair to the estimated 20,000 British and American men, along with over 10,000 Spanish, that died in it, mostly from diseases. Of the roughly 4,000 American volunteers who served in the Caribbean theater, less than 300 lived to see their homes again. So, who was Jenkins, and how did an encounter in 1731 start an actual shooting war eight years later?! Robert Jenkins was a British sea captain whose ear was partially severed as punishment for Spanish coast guard agents finding smuggled sugar aboard his brig, Rebecca. For eight years he presented his case to Parliament for redress. However, Parliament ignored Jenkins until a new government reasoned a successful war against Spain might win for Britain the prized Asiento de Negros. The Asiento was a monopoly contract to bring enslaved Africans into Spanish ports, but more importantly, the loathsome slave trade aside, cynical politicians anticipated this “commercial illusion” would afford British merchants the ability to smuggle British manufactured goods into Spanish ports as well; in essence the same crime for which Jenkins’ ear had been maimed.

With Spanish forces initially stretched thin defending their Caribbean colonies, Oglethorpe gathered his forces, including the Highlanders, to invade Florida. Rolling up small forts and towns in route including the first town for Free Blacks in America, Ft. Mose, Oglethorpe reached St. Augustine in the summer of 1740. However, his supporting British fleet refused to sail under the formidable guns of Castillo San Marcos whose unique coquina walls easily rebuffed British cannon balls. Despite summer heat, Oglethorpe marched his troops daily back and forth in front of the fort hoping to cower or starve the defenders into submission. Disaster struck in the form of former slave named Francisco Menendez.

Slaves escaping British colonies, South Carolina in Menendez’s case, gained freedom by reaching Florida, accepting Catholicism and doing four years of indentured servitude. Menendez took his master’s name and captained a Free Black militia at Fort Mose. Oglethorpe had ordered a covering force of Redcoats and Highlanders under Colonel John Palmer to never camp on the same ground two nights in a row. However, on 14 June, Palmer’s force had camped in the ruins of Ft. Mose for a week, making their whereabouts well known to the Spanish and Menedez. Palmer considered the Highlanders undisciplined, and few Scots understood him because he couldn’t speak Gaelic. Taken by surprise before dawn by superior forces of Spanish and Free Blacks, Palmer, three captains and three lieutenants were soon killed. While the Highlanders fought bravely; over thirty died along with scores of regular Redcoats; over three dozen British were taken prisoner. With Palmer’s contingent virtually annihilated, and the British fleet soon sailing away to avoid hurricane season, Oglethorpe, withdrew from Florida.

With British forces defeated at Cartagena and otherwise bogged down, 1742 presented Spain’s chance for revenge for Oglethorpe’s invasion. Lead by the defender of St. Augustine, Governor Don Manuel de Montiano, upwards of two thousand Spanish troops sailed to attack the British forts on Saint Simons Island which protected Georgia’s then capital of Savannah. The Highlanders, withdrawn from Ft. Amelia, were in the thick of the main battle at Bloody Marsh on 7 July that saw two hundred Spaniards fall dead or wounded before the Spanish retreated to their landing zone. Still vastly outnumbered, the next day Oglethorpe employed spy-craft. He released a prisoner with a “secret” message to a French defector knowing it would find its way to Montiano instead. The message implied the British army, which was in fact only a third as large as Montiano’s, was much stronger and the defector’s reports to Montiano that the British were weak would help Oglethorpe set a trap for the Spanish should they venture forward again. The hapless, French defector was immediately executed as a spy! Next, Oglethorpe stationed his drummers across his entire front to make his force sound large. Finally, Oglethorpe’s Indians allies massacred a small party sent out to find fresh drinking water. Montiano had had enough. Beaten at his front, with no reliable intelligence on Oglethorpe’s actual strength, and with no fresh water for his men, he ordered his army to sail back to St. Augustine thus ending hostilities.


Despite the deaths of tens of thousands of men, the result of the War of Jenkins’ Ear was Status Quo Antebellum. Spain retained the Asiento de Negros. Having helped save Geogia and perhaps even more of British North America from Spanish conquest, Highlanders were never reposted to Amelia Island. In 1751 slavery was introduced to Georgia by the Trustees over Oglethorpe’s strong objection. His loyal Highlanders nobly signed a petition against slavery.


    References

The War of Jenkins’ Ear: The Forgotten Struggle for North and South Americaby Robert Gaudi

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