The Alligator, Part 1 of 2

A sketch of the pirate fighting ship, the U.S. Schooner Alligator. The original purpose of the ship was to sail to Africa to find a colony for freed slaves. (Photo courtesy of Jerry Wilkinson/Historical Preservation Society of the Upper Keys)
A sketch of the pirate fighting ship, the U.S. Schooner Alligator. The original purpose of the ship was to sail to Africa to find a colony for freed slaves. (Photo courtesy of Jerry Wilkinson/Historical Preservation Society of the Upper Keys)

Just about everybody loves a good pirate tale. Fortunately, the Florida Keys have a few to offer. Make no mistake: these islands are not ripe with authenticated pirate stories. However, a few documented accounts of piratical activities have been recorded in and around the archipelago. In fact, one such incident involved the namesake of one of Islamorada's more familiar landmarks.

The story starts in the Boston Navy Yard where the U.S. Schooner Alligator was constructed. The 86-foot long ship-of-war was one of four swift 12-gun schooners built to fight pirates and slave traders. The Alligator, commissioned in March, 1821 was first used to ferry representatives of the American Colonizing Society to the west coast of Africa. They made the trip in hopes of finding land on which to create a colony.

The objective of the society, formed in 1817, was to transport freed slaves back to Africa. The emigration was considered an alternative to the emancipation process that was beginning in America and their colony was ultimately established in 1822. In 1847, it became the Republic of Liberia. By 1867, 13,000 freed slaves had been sent there.

The Alligator returned to America and, in June, 1822, command was reassigned to Lt. William H. Allen. He was directed to join the West Indies Squadron and hunt pirates in the Caribbean and Florida Straits. Including Allen and Lt. Dale, Allen's second in command, the ship was armed with a crew of nine officers and 45 seamen and marines.

By November, the Alligator was patrolling off the northern of coast of Cuba. November 8, the ship sailed into the harbor at Matanzas where local merchants had been helping two Americans outfit a schooner, the Ploughboy, with the necessary means to fight pirates holding the Americans' ships and crews hostage.

Before the Alligator's anchors could be dropped, the Americans approached Lt. Allen and informed him of the $7,000 ransom demand. The pirates claimed they would burn the ships and every man aboard if they were not paid. Allen ordered the anchors hoisted and the Alligator set sail for Guajaba to the east. The Ploughboy followed.

The captured ships were tucked away in a cove. Lieutenant Allen and his men spotted their masts sticking up from the tree line in the early hours of the following morning. Because the cove was shallow, the Alligator proved unable to approach. Allen ordered three auxiliary boats lowered, a launch, cutter, and a gig. Allen took command of the launch and Dale the cutter. Four men got into the gig and everyone rowed at full steam into the cove.

The name, Revenge, was carved into the side of the pirate schooner; the decks were crowded with approximately 30 cutthroats. A broadside of round and grapeshot was fired at the approaching marines, but the aim proved wild. None of the Alligator's auxiliary ships suffered damage.

To the contrary, as the marines drew closer, accurate musket fire began to cripple the pirates who were forced to attempt escape. There was not wind enough for sails, so the pirates heaved with their long oars and tried to paddle the Revenge away.

Over the course of two hours, the low speed chase covered about 10 miles, but not before another pirate ship joined the fray. The second schooner had 60 pirates on board and though Allen's men were outnumbered two to one, the marines fought on. Lt. Allen was hit twice by gunfire and though mortally wounded, continued to issue both orders and encouragement.

During the 30 minute skirmish, four marines were injured and two killed, including Lieutenant Allen. The Revenge was abandoned and the surviving pirates escaped aboard the second pirate schooner. Command of the Alligator shifted to Lt. Dale.

Nine days after the fight, Dale and the Alligator were escorting the liberated American ships and the Revenge, to Norfolk, Va. One of the American ships, the Ann Maria, was a merchant vessel carrying a load of molasses. Like most of the convoy, the Ann Maria was built for capacity, not speed and it did not take long for the convoy, including the Ann Maria, to fall behind.

Now, before leaving Matanzas, Lt. Dale had learned that pirates were planning to attack the convoy's stragglers. Dale's concern only increased as the ships fell increasingly behind. To slow the Alligator, Dale ordered the schooner to begin tacking maneuvers. Because the lieutenant understood the treacherous nature of these waters, he ordered soundings taken every 30 minutes. At 9 p.m., Nov. 19, the water showed 270 feet. At approximately 9:30 p.m., the Alligator came to a sudden halt.

Stay tuned for the fate of the Alligator and the rise of Commodore David Porter's smaller, faster, more effective version of the West Indies Squadron.

Brad Bertelli is a published author of four books on Florida and Florida Keys history. His column will appear bi-weekly in The Reporter. Reach Brad with comments and questions at