Heyday for Pirates, 1817-1818

This peaceful interlude was of short duration, for in June 1817, arrived the picturesque “General” Gregor McGregor. One day a fisherman came hurriedly into Fernandina with news that some men in a boat from a vessel had hailed him, and after inquiring as to number of inhabitants in the town, the means of defense, the number and character of the garrison, had commanded him to return to the city and tell the commandant that General Sir Gregor McGregor with his fleet and army was off the bar on his way to take possession of the town. When the five vessels were in sight the leading men of the town met and called upon the commandant of the garrison, Colonel Morales, to find out what action he proposed to take. The Colonel was a fat old man who loved his ease. He threw up his hands with the words, “What can I do? There is just one thing for me to do, and that is to take the men in the garrison, march them to St. Augustine and report to the Governor.” One of the citizens warned him that he would be put in irons and sent to Havana for such a cowardly act, but Morales proceeded to carry out his intention, leaving the town defenseless. Many of the inhabitants sent their families out of the town, some left themselves, while some few remained in Fernandina to await further developments.

Letters of J. Skinner, postmaster of Philadelphia, on file in the State Department at Washington, give evidence of MacGregor’s American backing.1 Skinner seems to have been close to administration leaders. He was consulted by MacGregor, he says, in regard to a plan for capturing Amelia Island and making it independent of Spanish rule. This was to be the first step in acquiring use of the harbor of Fernandina as a basis for MacGregor’s own South American operations, since he considered it one of the best harbors on the coast, and a familiar resort for the type of men needed for the South American enterprise, a doubtful compliment from any viewpoint. ‘

At first Skinner thought MacGregor an English spy, but finally concluded that he was a visionary, and harmless, if not actually beneficial, as far as the interests of the United States were concerned. MacGregor was a handsome young Scotsman of 31, the grandson of the Laird of Inverardine. He had been for some years interested in the cause of South American independence, had served under Miranda and later under Bolivar, his relative by marriage. In spite of these Spanish affiliations, there was feeling against him in Fernandina so he determined on another approach to the cause.

Understanding that the United States Government would not oppose him, MacGregor gained the promise of financial support in Philadelphia. He enlisted recruits in Charleston, young and adventurous spirits, some belonging to the first families in the city, many of whom had served in the late war with England. In Savannah he enlisted more recruits, but these were of a more mercenary type, who were to be paid $10 a month for their services. In Savannah also he is said to have obtained an advance on a loan of $30,000 in return for which he was to give the mercantile house making the loan 30,000 acres of land in East Florida. This mercantile house sent at least one spy to Fernandina, and MacGregor’s plan of attack was based on the information he brought back. It was learned that the Spanish garrison at Fernandina consisted of but 54 men, officers included, and that there were only 200 men in the town capable of bearing arms. MacGregor decided to make his attack on a Sunday, when many of the soldiers would be absent from the fort. He marched his 55 men in open order, to give the appearance of a large force.

The march on the fort took place on Sunday, June 29, 1817. Morales, believing attackers to be much larger in number than they in reality were, surrendered the fort to them. The band that entered Fernandina had waded through the marsh and though wet and muddy, were truly impressive, each man with a long green plume in his hat. This insignia turned out later to be ordinary dog fennel, probably used to ward off the swarms of insects. The men took possession of the abandoned houses. MacGregor established himself in the finest house in town. He assumed great style; sentinels paced before his door and formalities had to be observed in approaching him, though nothing could exceed his affability, once admission to his presence was gained. He entertained lavishly, gave grand dinners, and was profuse in his hospitality. In company he was jolly and good-natured. As a prank he told his Spanish wife (who spoke no English) to greet her American guests with “Go to Hell.” “Why do they laugh?” she asked wonderingly. “Because you speak so charmingly, my dear,” he replied.

MacGregor issued daily documents ornate with ribbons and seals. His followers wore on the left arm a shield of red cloth with a motto and a wreath of oak and laurel leaves embroidered in yellow silk. His flag was a green cross on white which he promised soon to plant on “the proud walls of St. Augustine.” He declared all Florida in a state of blockade from the south side of Amelia River to the Perdido River, and signed his communication to Morales, “Gregor MacGregor, Brigadier General of the Armies of the United Provinces of New Granada and Venuezuela and General-in-Chief of that Army, destined to emancipate the province of both Floridas, under the commission of the Supreme Government of Mexico, and South America,” etc., etc.

The invaders set up a town government, appointed a mayor, opened stores for the sale of the valuable merchandise brought with them, and solicited traffic with the town people. The latter did not neglect the opportunity to dispose of their produce. They received good prices for their chickens and eggs, or exchanged them for such delicacies as coffee, tea, sugar and cocoa, Fernandina was made a free port, and large quantities of dutiable goods were smuggled into the United States. The harbor was visited by vessels from many countries, and trade was good.

MacGregor’s popularity and power, however, were short-lived. Raids on neighboring settlements made him unpopular with the inhabitants of East Florida, and the Spaniards prepared to attack him. His paper money proved worthless, he got into debt, the expected help from the north did not materialize, and his men began to contract fever. Just as a battle was impending with the Spaniards, Ruggles Hubbard, high sheriff of New York, arrived, but since he had not brought with him the financial assistance which MacGregor was expecting, the general deemed it prudent to depart for New Providence, from whence he did not return.

In abandoning the cause of freedom MacGregor perforce surrendered the command of Amelia to Jared Irwin. The latter had been a member of Congress from the State of Pennsylvania. Irwin, with feverish haste, prepared for an impending Spanish attack on the island. He collected what force he could from the heterogeneous elements then loose in the vicinity and enlisted the services of several independent privateers in the port of Fernandina. In a few days the Spaniards appeared before the town and the battle began. It was won by the poor marksmanship of Irwin’s privateers, who, training their guns on the Spanish battery on McClure’s Hill, overshot their mark so that shells fell among the Spanish troops massed below. Several were killed and a number wounded. The Spanish commander, becoming panic-stricken at the unexpected development, ordered a retreat, leaving Irwin in undisputed possession of Amelia Island. This was September 13, 1817. After the battle, Hubbard, who had been at St. Mary’s, joined Irwin, These two American politicians entered into a combine to retain possession of Amelia Island, not for the purpose of conquering Florida, but for the establishment of a rendezvous for the swarms of privateers that then infested the Atlantic and the Gulf of Mexico. Hubbard became the Civil Governor and Irwin the naval and military chief of Amelia. There is strong evidence that they were allied with certain large American mercantile establishments that dealt in prize goods illegally taken upon the high seas.

The high sheriff of New York and the former Congressman from Pennsylvania were busily engaged in organizing a government for their new acquisition when, about the first of October, the fleet of the Frenchman, Luis Aury, sailed into the harbor of Fernandina with two privateers. Like the LaFittes, he was a client of Edward Livingston. Appointed first governor of Texas under the New Mexican Government, he had been operating against the Spanish on the Gulf Coast and ‘had acquired thirteen ships. It is said that his prizes were worth $60,000. Governor Hubbard and Colonel Irwin appealed to Aury for financial assistance in perfecting their establishment at Amelia, but Aury refused unless he were made supreme chief. The Americans objected to this agreement. Contention lasted several days; Aury was preparing to leave when the two others yielded. It was finally agreed that Hubbard should retain his title of Civil Governor of the island, but that Aury should be military chief and Irwin adjutant-general. Aury, in his capacity of a Mexican official hoisted the flag of that republic over Amelia Island. So with the buccaneers lined up at attention, Amelia Island was annexed to the Republic of Mexico on the 4th of October, 1817. This flag’s device was a coiled reptile.

Aury had brought with him to Amelia Island a band of Santo Domingo Negroes, known as “Aury’s Blacks,” together with outcasts of various other nationalities, among them remnants of LaFitte’s band. LaFitte himself is reported to have visited Fernandina as freely as he did New Orleans. One lady recalled borrowing a book from a cultured visitor in town and finding the name LaFitte on the flyleaf. When she questioned the donor, he laughed and said “LaFitte walks the street like any other man,”

Irwin continued in the office of adjutant-general under Aury. The establishment of Amelia was now a piratical institution of the first class, slave ships taken upon the high seas being the chief source of revenue. In two months more than a thousand slaves were smuggled through the port of Fernandina. Conditions at this time are graphically portrayed in Roland Bank’s novel, Black Ivory. Other cargoes consisted of coffee, tea, cocoa, wines, liquors and costly fabrics. During Aury’s command there were as many as eight prizes in the port at one time. One of the most interesting was a cargo of a thousand boxes of cigars made expressly for the King of Spain.

The compromise agreement between the Americans and Aury was soon broken and affairs of state drifted into the utmost confusion. Two factions developed, one headed by Hubbard, called the American party, and the other led by Aury, known as the French party. The two were on the point of open warfare when Hubbard died of an attack of yellow fever, after which Aury gained control of Amelia.

The United States Government had kept an eye on affairs at Amelia, and as soon as it became apparent that these were in no way tending toward a conquest of Florida, President Monroe invoked a secret law of authority and ordered a military and naval force to the Spanish waters of Amelia to run Aury out. On December 23, 1817, Capt. J. E. Henry of the United States corvette John Adams demanded Aury’s surrender. Aury protested but made no resistance. The American troops landed, marched up to the fort at Fernandina to the tunes of Hail Columbia and Yankee Doodle, and hoisted the American flag. Aury sailed away to continue his operations as a privateer until his death on the Island of Old Providence in 1821.

The Spanish minister protested the occupation, to which John Quincy Adams, the Secretary of State, countered with a long shrewd reply. He broadly hinted that since Florida had become: too troublesome for Spain, she ought to cede it to the United States, and enumerated five terms for such a cession. The Spanish minister, in a reply also as thick as a volume, gave his reasons why Spain would never consent to a cession on any terms.

While the United States was holding Fernandina “in trust” for Spain, all duties on goods coming to the port were paid to the American collector of customs at St. Mary’s, Georgia. The Spanish authorities at St. Augustine were so bitter against this arrangement that on November 21, 1818, they sold ten horse-loads of arms and ammunition to the Indians, urging the natives to attack the Americans who were then holding the Spanish ports at Pensacola, St. Marks, and Fernandina. Major Fanning, in charge at St. Marks, reported three English vessels trading arms to the Indians on the West Coast, one at Tampa and two at the mouth of the Suwannee River.

Some of this ill-will was vented when Captain Miller of the Spanish forces fired on Augustus Santee, a resident of Fernandina, and two American soldiers who had left the shelter of the town and were visiting near the mouth of the St. Johns River. The three men were taken to St. Augustine as prisoners over the protest of General Gaines, American Commander at Fernandina.

In 1818, a yellow fever epidemic broke out which was so devastating that even the United States Marines left. The town was almost depopulated, and many years passed before people returned in appreciable numbers to live there.

Jackson’s raid into West Florida caused a temporary lull in negotiations for the cession of Florida, but afterwards they were resumed, and Adams’ terms were the basis on which Florida was finally ceded to the United States. This was called a sale, but actually no money changed hands, claims against the Spanish Government for damages to property of Americans during the Patriots’ Rebellion cancelling the purchase price of Florida. On July 10, 1821, the Spanish flag was lowered on Fort San Carlos and the Stars and Stripes “announced the second acquisition to the young nation of the New World.”


The above material was written and compiled by “Workers of the Writers’ Program of the Works Projects Administration in the State of Florida, Sponsored by the Florida State Planning Board, and copyrighted by the City Commission of Fernandina in 1940.” There were no subsequent copyrights on this material and the material entered the public domain in 1968, or 28 years after the publication of material. This material uses phraseology and words which may be considered offensive to readers today.

  1. Skinner, J.; “Letters Relating to MacGregor’s Attempted Conquest of East Florida, 1817”; Florida Historical Quarterly, Vol. 5, Number 1, Article 8, 1926. https://stars.library.ucf.edu/fhq/vol5/iss1/8 : accessed 4/29/2022 []

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