Pirates in the Florida Keys?
by Bonnie Barnes March 17, 2021 | Vol. 1, No. 7
Florida Keys Stories
James Biddle, the first commander of the West Indies Squadron, was relieved of his duty in 1822. The deeper-draft ships deployed by him struggled to pursue the pirates who favored shallow-draft vessels capable of better navigating the shoals and reefs of the West Indies.
December 22, 1822, Secretary of the Navy Smith Thompson replaced Biddle with Commodore David Porter, appointing him “to command the vessels-of-war of the United States on the West India station… for the suppression of piracy.”
Recognizing Biddle’s squadron’s limitations, Porter demanded 10 Chesapeake Bay schooners, ships not unlike those favored by his foes. Among Porter’s ships was the Mosquito Fleet, a specialized force of five, swift shallow-draft ships capable of agile navigation. They were appropriately named Mosquito, Sandfly, Gnat, Midge, and Gallinipper (a gallinipper is a large mosquito or biting fly). Porter also outfitted the side-wheel New York ferryboat Seagull as an armed base of operations.
Commodore David Porter established the squadron’s base of operations on Thompson’s Island in 1823. Seventeen guns were fired in salute at eight o’clock on the morning of April 6. The American flag was raised over the island. What Porter and other government officials recognized as Thompson’s Island, named for Secretary of the Navy Smith Thompson, was more commonly known as Key West. Porter declared the settlement Allenton, named after the fallen Lieutenant Allen killed during a pirate skirmish off the coast of Cuba while in command of the U.S.S. Schooner Alligator the year before.
Utilizing the right vessels and having 1,100 sailors at his command, Porter proved an effective leader who made relatively short work of the pirates of the West Indies. It has been suggested that one of his successes was ridding the Florida Keys of pirates. The documentation supporting the assertion is limited. One of those documents is the “Map of the West Indies, and History of Piracies Committed on American Seamen & Commerce,” engraved by N. & S.S. Jocelyn, Monson & Co. Publisher, 1825. Marathon resident Brian Schmitt shared the comprehensive map of the West Indies that also provides a historical record of 93 accounts of piracy in its accompanying text “Piratical Depredations and Barbarities, From May 1818, to August 1825, inclusive.”
One notable aspect of the record is that the vast majority of the listed piratical events occurred off Puerto Rico, Cuba, and the Yucatan Peninsula. It should also be noted that, contrary to the piratical romance often portrayed in the movies and on television, though not so much in the Starz series Black Sails, none exists in the document. There was a reason the map makers chose the word “depredations” in the subheading. The March 1, 1823, entry read: “The brig Bellisarius, Perkins, at Kennebunk, was boarded in the bay of Campeachy, and robbed of every thing. They stabbed the captain in several places, cut off his arms, and one of his thighs—then put oakum dipped in oil in his mouth and under him, and set the whole on fire, which soon put an end to his sufferings.”
Out of the 93 acts of piracy recorded on the document, only two mentions the Florida Keys. The first is the 1819 attack on the schooner Adeline, Ellis, “boarded off the Florida Keys by a piratical boat which robbed her of every thing, and left her.” The second event occurs in September 1822. “The brig Mary Ann, of Boston was boarded by a piratical schooner close in with Stirrup Key, and robbed of her whole cargo. Vessel given up.”
There is an island in the Florida Keys called Stirrup Key. The name dates back to the Gauld chart of 1775 and identifies a small island on the Gulf side of Key Vaca found just east of Key Vaca Cut. The Stirrup Key stated in the event could very well be the same island that is today linked to Key Vaca by Stirrup Key Road.