USS Schooner Alligator

US-Schooner-AlligatorThe USS Schooner Alligator 1822

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 FloridaStraits. 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.

On November 8, the ship sailed into the harbor at Matanzas, Cuba where local merchants had been helping two Americans outfit the schooner, 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 row 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 further 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 depth 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.

Four marines were wounded and two killed when the men of the U.S. Schooner Alligator attacked pirates holed up in a small cove near Guajaba, on the eastern coast of Cuba.

The Alligator’s commander, Lt. Allen, died from multiple wounds suffered in the fray leaving his second-in-command, Lt. Dale, in charge. Dale’s first mission was escorting the convoy of liberated American ships, including the confiscated pirate schooner, Revenge, from Cuba to Norfolk, Va.

Before departing Cuba, Lt. Dale heard rumors that pirates were planning to attack his convoy’s stragglers. The problem was that the Alligator was a ship of war built for speed while the convoy was a small fleet of merchant ships built largely for commerce. Dale became distressed as the Alligator sailed along and the convoy continued to slowly drift out of sight.

He gave orders to begin tacking maneuvers to allow the convoy to catch up. While sailing toward the Florida Reef, soundings were taken every 30 minutes. November 19, 1822, 9 p.m., the water measured 270 feet deep. Approximately 30 minutes later, the Alligator came to a sudden halt roughly 3.5 miles off of Upper Matecumbe Key.

The ship was crashing through the water with a full head of steam when it ran afoul of one of the largest spur and groove reef formations in the Upper Keys. It did not take long for Dale to determine the 86-foot ship was hung up pretty good. A longboat was lowered and a kedge anchor rowed out to the deeper waters to the east. The anchor was dropped and the men aboard the stricken Alligator heaved in an attempt to physically drag the ship off of the corals, but the line broke.

Orders were given to lighten the ship and the first to go overboard were the cannons and their shot. Two smaller guns, carronades, were left aboard. The first night and the following day were spent throwing anchor chains, spare sails, everything and anything that might help lighten the load over the side and into the clear turquoise water. It was hoped that with the next high tide, the ship would prove sufficiently buoyant to be refloated. Instead, the wind shifted and pushed the ship harder against the coral bank.

The following morning, another kedge anchor was lowered into a longboat and rowed out to deeper water. The anchor was dropped and again, the crew heaved. Unfortunately, it never took hold and the men only succeeded in dragging the anchor across the limestone substrate and back to the ship. In the meantime, a wrecking crew sailed up and offered assistance. Lieutenant Dale did not formally engage the wreck master, but asked him to hold the Alligator’s papers and what cash they had on hand.

Dale and his crew waited for the convoy to catch up and a few hours later, Dale and his men spotted the first ship. The carronades were fired and the shots attracted the attention of the Ann Maria and her load of molasses. The Ann Maria approached the stranded ship and anchored in the deeper waters to the east. The operating sails and accompanying tackle were loaded on to the Ann Maria. In lieu of leaving what was left of the Alligator for pirates to scavenge like cockroaches, the ship was set afire until she exploded. Kaboom!

The following year, February, 1823, Commodore David Porter took command of the West Indies Squadron, the branch of the Navy that the Alligator had served under. Porter recognized the limitations the squadron had faced while under command of its former boss, James Biddle. The heavy drafted ships employed by Biddle were incapable of pursuing pirates who favored shallow draft vessels capable of navigating the shoals and reefs that can make these waters tricky.

Porter demanded 10 Chesapeake Bay schooners, ships not unlike those used by his foes. He also outfitted the side-wheel New York ferryboat, Sea Gull, as an armed base of operations. Porter established a naval depot on Key West, an island being referred to as Thompson’s Island at the time. In April, 1823 he declared the depot Allenton in honor of Lt. William Allen, who had been shot to death by those pirates aboard the Revenge the year before.

Suffice it to say, Porter was exceedingly more effective in ridding the area of pirates.

While Biddle turned those suspected over to an American court system, Porter went another route and handed his suspects to British pirate hunters who would hang them without benefit of a court hearing.

alligator-lighthouse-islamarodaToday, the lighthouse standing approximately 3.5 miles off of Upper Matecumbe Key marks the general location of where the Alligator crashed in 1822. The reef it marks acquired the name Alligator Reef. The lighthouse, Alligator Lighthouse, was built in 1873.

~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