Commodore Porter’s Anti-Piracy Squadron at Key West Harbor in 1823. MONROE COUNTY LIBRARY COLLECTION/Contributed

Editor’s Note: This is the second part in a series on pirate encounters off the Florida Keys.

Pirate attacks on American ships sailing in foreign waters were nothing unusual in 1822. The Ann Maria, from New York, was victimized by pirates operating in Cuban waters twice, by the same pirates, between September and November. The Ann Maria was rescued the second time by the U.S. schooner Alligator, one of the ships assigned to the famed anti-piracy West Indies Squadron.

The Ann Maria was not the only American ship liberated that day. Among others being held was the schooner Iris and it was the desperation of the master of the Iris, Freeman Mayo, that brought the Alligator to the pirate cove on Nov. 9.

On Nov. 4, 1822, the Iris sailed about 40 miles off the port city of Matanzas, Cuba. At about 8 a.m., Mayo observed two schooners sailing out from the coast. As they approached, one of the schooners fired its 18-pounder twice, sending cannonballs over the deck of the Iris as a request for her to lower her sails and await company. When Mayo complied, a crew of six men boarded. They were armed with pistols, cutlasses and long knives and announced themselves as pirates. To impress the point, when they boarded, the pirate captain fired his pistol over the head of Mayo.

The pirates held Mayo and his crew hostage while they searched the ship for potential booty. However, when the pirates attempted to crew the ship and sail away with their prize, they could not perform the task. To help the pirates, they brought half the hostages back on deck to man the lines and sails. Once they did, the pirate captain sailed the Iris closer to the Cuban coast and dropped the anchor about a quarter-mile off the beach. When the sails were dropped and secured, and the anchor was resting on the bottom, the pirates forced the master and crew into the forecastle’s confines (the upper deck’s forward part).

According to an account delivered by Mayo, they were crammed inside the forecastle without food, water or “barely enough air for them all to breathe.” They also, apparently, found Mayo’s clothes when they raided his quarters, and when they did, they played dress-up. At midnight, Mayo was separated from his crew and brought to one of the ship’s cabins. The pirates beat him with their pistols, choked him, and threatened to end his life. Though they returned Mayo to the forecastle, they were not done and only exchanged him for the cook and cabin boy, whom they beat and terrorized, too.

When the sun rose on Nov. 5, the Iris sailed about five miles away from Point Yeacoa, and that night, the pirates robbed the master and crew of all their clothing, money and watches. The next day, they sailed five miles into a bay and anchored near another schooner captured by the pirates the same day as the Iris. There, the pirates began to offload the ship’s cargo, including 100 boxes of axes, about 40 casks of nails, anchors, rigging, two compasses and about 300 pounds of bread and other food staples. Next, the pirate captain ordered his crew to search the schooner for one more hour in case they missed anything of value and, after that, to kill the ship’s master and crew and burn the ship.

Mayo pleaded with the captain to let his men live, give them a long boat, some bread and water and allow them to make their way to the Florida coast. The captain refused, telling Mayo that he would spare none of them. Fortunately for Mayo, one of the other pirates tried to talk the captain out of his decision. That pirate was told to do his duty, or he would be killed, too. Mayo then proposed going to Matanzas to raise money to ransom their lives and ship. After a brief hesitation, the captain agreed to give him three days to come back with $6,000 ($7,000 in some accounts), or he would continue with his plan. 

The captain brought Mayo seven miles offshore of Matanzas and set him off in a long boat. Mayo arrived at the port at 1 p.m. and called on the governor to help, but he refused. Also, American merchants at the port refused to help, telling Mayo that negotiating with the pirates would set a bad precedent. At the dock, a group of American shipmasters agreed to help by assembling a force of their crews to fight the pirates. Captain Wilkins of the pilot boat schooner Ploughboy from Philadelphia offered his ship and services. A canon, an 18-pounder, was loaded onto the ship, as were 50 muskets, pistols and cutlasses. 

About 50 men had gathered near the Ploughboy, but as it became closer to the time to embark on their mission, some of the men began to get cold feet, back out and discourage others from the operation. Unsure of how to proceed, Mayo saw potential help arrive when the U.S. schooner Alligator sailed into port on Nov. 8. After the ship arrived, Mayo boarded and pleaded his case to Lt. William Allen. Shortly after that, the Alligator, followed by the Ploughboy, sailed away from Matanzas and into a pirate fight.

Avast ye! In next week’s edition of Florida Keys History with Brad Bertelli, the story of the pirate fight and the fate of Lt. Allen will be explored. Until then hearties, yo ho ho!

Brad Bertelli is an author, speaker, Florida Keys historian, and Honorary Conch who has been writing about the local history for two decades. Brad has called the Florida Keys home since 2001. He is the author of eight books, including The Florida Keys Skunk Ape Files, a book of historical fiction that blends two of his favorite subjects, the local history and Florida’s Bigfoot, the Skunk Ape. His latest book, Florida Keys History with Brad Bertelli, Volume 1, shares fascinating glimpses into the rich and sometimes surprising histories of the Florida Keys. To satisfy your daily history fix, join his Facebook group Florida Keys History with Brad Bertelli.