
He was a pompous swashbuckler with visions of grandeur and a desire to gain fame and notoriety. He made an impact (somewhat oddly) on the history of the southeastern coast. Sadly, his lofty schemes faded into discarded daydreams.
He was Gregor MacGregor, born in Scotland in 1786. Young Gregor joined the Black Watch to make his fortune, but at the age of 20 he resigned after learning that Simon Bolivar was recruiting officers to serve in the Army of Liberation then fighting to free Latin America from the Spanish Empire. Gregor sailed for Caracas, Venezuela where in 1811 he received his commission from Bolivar himself. He married a senorita and made such a good impression on the battlefield that he was given the rank of general in the Venezuelan Army.
Over the next 5 years Gregor distinguished himself in battle winning victory upon victory while displaying a rare combination of personal bravery, tactical genius and superior strategic planning. He rapidly rose to the rank of General of Cavalry, then General of Brigade, and finally General of Division. To crown this achievement, Gregor was rewarded with the highest honor of being named to the Order of Liberators, Simon Bolivar personally making the award. Bolivar's affection for this courageous clansman must have been profound, for soon Gregor MacGregor married Donna Josepha, BolivarŐs niece, whose great beauty was widely admired and perhaps more widely envied.
Despite having won wealth, fame, and great social status, Gregor was not content to rest on his laurels. Taking a small band of only 150 carefully selected men in 2 small ships, Gregor launched a series of wildly successful raids on the Spanish forts guarding the Isthmus of Panama. Having seized the key strategic outposts controlling the Isthmus and thus the western Caribbean, Gregor sailed up the east coast of what today is Nicaragua, seeking but not finding other Spanish strongholds to capture, eventually landing on the Mosquito Coast. There he befriended an elderly Indian chief who granted to Gregor the rights to vast tracts of undeveloped, some would say worthless, miasmal swamplands.
Looking for bigger things, he went to America to organize an expedition that would make history. At that time Spain's grip on the Southeast was divided into East and West Florida. In Baltimore he spread his grandiose plans to invade Florida and stir the people to form a free government and annex themselves to the U.S. He received some financial aid and promises of troops. In Charleston he bought a big schooner and enlisted several followers, some from the finest families. In Savannah he got more recruits, but these tended to be a rough bunch, not trained as soldiers in any way. By now he had a sum of money and about 150 men. In Darien (his final stop before Florida) he seems to have had no success. Even worse, some of his troops deserted because of rigid discipline.
When MacGregor sailed down the Inland Passage, headed for Fernandina, his hopes were high. By this time he had only 55 followers--and later reports said they were mostly ragged boys and tattered oldsters, many of them drunk.
| The following letters
were written by General MacGregor and printed in an issue of the New
Hampshire Patriot dated July 29, 1817, less than a month after his
triumph on Amelia Island.
PROCLAMATION Gregor Mac Gregor, Brigadier General of the armies of the United Provinces of New Grenada and Venezuela, and general in chief of the armies for the two Floridas, commissioned by the Supreme Director of Mexico, South America, &c. To the inhabitants of the Island of Amelia:
Your brethren of
Mexico, Buenos Aryes, New Grenada and Venezuela, who are so gloriously
engaged in fighting for that inestimable gift which nature has bestowed
upon her children, and which all civilized nations have endeavored to
secure by social compact - desirous that all the sons of Columbia should
participate in the imprescriptable right - have confided to me the command
of the land and naval forces. Friends, or enemies of our present system of emancipation, whoever you be, what I say unto you is the language of truth; it is the only language becoming a man of honor, and as such I swear to adhere, religiously to the tenor of this proclamation.
Dated at headquarters, Amelia Island, |
After landing at the north end of Amelia Island on June 29, 1817, they advanced toward the fort, but soon enough were soggy and dirty from going through the marsh. This was quite an army--and they wore green plumes in their hats. (The plumes were stalks of dog fennel, a weed with a daisy-like flower on it, plucked from the swamps to repel insects.)
The Spaniards had only 54 men, and when they say the
enemy coming, they thought (just as predicted) that it was the advance guard of
a larger force! The Spanish commander struck his colors and surrendered without
a shot being fired. Maybe one of the reasons they were terror-stricken was the
appearance of the leader of the invaders. MacGregor, who was tall and
barrel-chested, made a magnificent appearance and looked a bit "Napoleonic" in a
splendid uniform. The general wore a sky-blue Balkan-style coat with enormous
white epaulets. His left breast was heavy with medals, and he had a fancy
ornamented belt with a sword at his side. On his head, his ample curly hair was
topped by a Scottish tam, and he had long sideburns.
In supreme triumph, MacGregor declared East Florida liberated from Spain. Then the two "armies" held a parley and the defeated Spanish leader agreed to march back to St. Augustine.
The
following is an extract of a letter from an officer in the Patriot Army to his
friend in Charlestown dated July 3, 1817:
"We arrived here on the memorable 29th of June, and after a march of ten
miles through the swamps, breast deep, we stormed the garrison, which
surrendered to us with 70 prisoners. We are now in peaceable possession, and the
inhabitants are well pleased. In a few days we move forward to storm St.
Augustine, where there are 500 men in a strong garrison, and are determined to
drive them out of it. Our 22 gun frigate, with 250 men, from New York, is off
the bar. We took two valuable schooners at Fernandina."
MacGregor set himself up in the finest house in town. He invited all citizens to visit him so he could greet them royally, and he and his wife entertained lavishly. He created the Green Cross of Florida, the Flag of his Kingdom

From this high point, however, MacGregor's career was all downhill. While he waited in Fernandina for promised financial aid and reinforcements, his men became disgusted (no payroll and not enough food) and began to desert. Feeling deceived and gypped by the Americans, he decided to give up. Besides, he heard that a large force of Spanish was coming to attack him. MacGregor left the island in September 1817.
King Gregor MacGregor ruled for 69 days.
He died in Caracas in 1845.
"SOLDIERS AND SAILORS! The 29th of June will be forever memorable in the annals of the independence of South America. On that day a body of brave men, animated by noble zeal for the happiness of mankind, advanced within musket shot of the guns at Fernandina, and awed the enemy into immediate capitulation, notwithstanding his very favorable position. This will be an everlasting proof of what the sons of freedom can achieve when fighting in a great and glorious cause, against a government which has trampled on all the natural and essential rights which descend from God to man. In the name of the Independent Governments of South America, which I have the honor to represent, I thank you for this first proof of your ardor and devotion to her cause; and I trust that, impelled by the same noble principles, you will soon be able to free the whole of the Floridas from tyranny and oppression. Then shall I hope to lead you to the continent of South America to gather fresh laurels in freedom's cause. Your names will be transmitted to the latest posterity as the first who formed a solid basis for the emancipation of those delightful and fruitful regions, now in a great part groaning under the oppressive hand of Spanish despotism. The children of South America will re-echo your names in their songs; your heroic deeds will be handed down to succeeding generation, and will cover yourselves, and your latest posterity, with a never fading wreath of glory. The path of honor is now open before you. Let those who distinguished themselves look forward with confidence to promotion and preferment. To perpetuate the memory of your valor I have decreed, and do decree, a shield of honor, to be worn on the left arm of every individual who has assisted or cooperated in the reduction of Island of Amelia; this shield will be round, or the diameter of four inches made of red cloth with this devise, "Vencedores de Amalia, 29th of June, 1817, 7 y 1," surrounded by a wreath of Laurel and Oak leaves, embroidered in gold for the officers, in yellow silk for the men. The colours of the corps of national artillery, the first squadron of cavalry, and the regiment of Columbia will have the same device embroidered on the right angle of the colours. Long live the conquerors of Amelia!"
Dated at headquarters, San
Fernandina
1st July, 1817, 7 & 1
GREGOR MAC GREGOR
Jph. de Yribarren, Secretary
Sources: New Hampshire Patriot dated July 29, 1817; Amelia now