A Florida Keys Pirate Tale or Two

In the early years of the 19th Century, piracy was still a problem in the West Indies, an area that not only included the islands of the Caribbean, but the waters surrounding the Florida peninsula. Rear Admiral Casper F. Goodrich studied the evidence of piratical activity in 1818 and published his findings in the U.S. Navy Proceedings Magazine, Volume 42. Among a number of other incidences involving pirates, Goodrich noted, “To these must be added the ship Emma Sophia, from Hamburg to Havana, which was boarded on December 19, by a piratical schooner of 30 tons, 1 gun, 30 men, between Bahama Bank and Sal Key Bank. The ship was sent to a small port formed by the Florida Isles and the Martyr’s Reef, and was plundered to the tune of $5,000.”

William Savage had been the supercargo of the ship and in charge of the ship’s cargo. In an excerpt from a letter written by Savage and printed in the Boston Daily Advertiser “Marine Journal” on February 3, 1819, he detailed his first-hand account of the events of that horrifying day. Savage wrote, “Davis, the spokesman, drew his knife and swore, that every man should die, unless he found the money, and first he would hang the supercargo. He called for a rope, which he had brought on board, fitted with a hangman’s noose, sent a man up the mizzen yard and rove it and brought the noose down — and one man held it, and another stood ready to hoist. Now, said Davis, tell me where is the money, where are your diamonds, or I will hang you this minute. In vain I repeated I had nothing more but my watch, which I offered and he refused. Once more, said he, will you tell? I have nothing to tell, said I. On with the rope, said the villain, and hoist away. The fellow with the noose came towards me, and I sprang overboard. They took me up, after some time apparently insensible.

They took off all my cloaths[sic], and laid me on my back on deck, naked as I was born, except having a blanket thrown over me. Here I laid five hours without moving hand or foot. Meanwhile they robbed us of every thing of the least value.” The publication of Savage’s letter preceded the signing of the Adams-Onis Treaty of 1819 that incorporated La Florida into the American fold. Terms of the deal were negotiated between John Quincy Adams, secretary of state under President James Monroe, and Luis de Onis, a foreign minister to King Ferdinand VII. While the agreement between the two parties was drafted and signed in 1819, it was not delivered to Washington and officially proclaimed until Feb. 22, 1821. The symbolic exchange of flags between the two countries did not occur until July 10. With the addition of the Florida Territory to the United States, President Monroe sought to clear the waters of pirates and initiated his anti-pirate policy in 1821.

James Biddle was given first command of the pirate-hunting fleet known as the West Indies Squadron. However, Biddle employed heavy-drafted ships incapable of pursuing the pirates who favored shallow-draft vessels better able to navigate the tricky shoals and coral reefs. Secretary of the Navy Smith Thompson replaced Biddle with Commodore David Porter on Dec. 22, 1822, appointing him “to command the vessels-of-war of the United States on the West India station… for the suppression of piracy.” Recognizing the limitations of Biddle’s squadron, Porter demanded 10 Chesapeake Bay schooners, ships not unlike those used by his foes. Also among Porter’s fleet was a specialized force of five, swift shallow-draft ships capable of agile navigation. They were the Mosquito, Sandfly, Gnat, Midge, and Gallinipper (a gallinipper is a large mosquito or biting fly). The squadron became known as the Mosquito Fleet.

In addition to establishing a naval depot on Key West, he outfitted the side-wheel New York ferryboat Sea Gull as an armed base of operations. Utilizing the right vessels and having 1,100 sailors at his command, Porter proved an effective leader. One of the reasons why Porter was more successful eradicating the pirate threat from these waters was that, unlike Biddle who turned suspected pirates over to an American court system, Porter handed his suspects over to British pirate hunters. The British would hang suspected pirates without benefit of a court hearing.

An example of piratical behavior hitting closer to the Upper Keys comes with the case of Port Monroe, a wrecking outpost established in the Vaca Key area circa 1823. Port Monroe had a reputation for operating beyond the scope of territorial law, which seems to be largely attributed to the relationship between Joshua Appelby, one of the founders of Port Monroe, and Charles Hopner of the Columbian privateer La Centilla.

Commodore Porter eventually got wind of the shenanigans afoot at Port Monroe and, in a letter to the Secretary of the Navy, wrote, “I am under the impression that the practice of wrecking Spanish vessels on the coast by Columbian cruisers [privateers], in order to secure their cargoes, has, for a long time past been pursued to a considerable extent, and that the establishment at Key Vacas [Port Monroe] was made with this object in view.” Appelby was subsequently arrested and taken to Rhode Island to stand trial.

Brad Bertelli is a published author of four books on Florida and Florida Keys history. He is the curator of the Keys History and Discovery Center, located at the Islander Resort. His column will appear every other week in The Reporter. Reach Brad with comments and questions at " target="_blank" rel="noopener noreferrer">.

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