Sunday Favorites: The Youngest Pirate

Charles Gibbs is pictured here, year unknown.

At high noon, on April 22, 1831, Charles Gibbs was hanged. At age 33, he had already established himself as one of the most villainous pirates in the U.S, confessing to over 400 murders over his lifetime. Gibbs had a reputation for taking no prisoners, instead opting to feed his captives to the sharks. But on April 22 on Ellis Island, New York, his reign of terror had finally come to an end. He was one of the last American pirates and last people convicted of piracy in the U.S.

Gibbs, formerly James D. Jeffers, was born on a Rhode Island farm in 1798. He was just a boy in his early teens when he decided to run away, forgoing farm life for an existence on the open sea.

Like so many other young seaman of his generation, he entered into an apprenticeship aboard an U.S. warship, Harriet. He participated in the War of 1812, serving on the Chesapeake during her famed battle with the Shannon. As a result of the skirmish, the 14-year-old was taken to England as a prisoner of war.

After a stint at Dartmoor Prison, Gibbs tried his hand at inn keeping, opening a small Manchester pub on Ann Street called the Tin Pot. His establishment attracted all the wrong people and Gibbs found himself indulging in his inventory more than he was tending bar.

Broke and beaten, Gibbs soon found himself aboard, Maria, the ship of Columbian privateer Jonathan Bell.

After a few months spent cruising around the Caribbean and the Gulf of Mexico. Gibbs and his crew mates decided they weren’t being paid enough for their efforts. Under Gibbs’s direction, the crew declared mutiny, dropped Bell and his mate on a deserted island and flew the notorious Black Flag, meaning they answered to no country.

The new band of pirates made the decision that day to burn all the ships they confiscated and kill all prisoners. Even one escaped witness testifying against them would easily warrant the death penalty.

A string of successful captures, rape and murder followed. Gibbs and his crew would trade the goods they accumulated from the ships to a Cuban dealer, then split the loot among them.

Gibbs and his pirate crew held their murderous pact with the highest regard; that is, until Gibbs laid eyes on a fair-haired Dutch girl.

In 1817, the pirates captured a Dutch vessel that carried a variety of fine European silver, silk and wine. The entire crew of 30 souls was immediately slaughtered, save a blonde beauty of 17. Gibbs, then 19,  didn’t have the heart to kill the woman, especially after she had fallen to her knees and pleaded for her life. Whether it was mercy or a sudden provoking point of perspective that made Gibbs change his mind, he allowed her to live with the understanding she would be his personal possession.

Gibbs took his new child bride to Cape Romano, an island on the Gulf Coast of Florida. He built her a sturdy pavilion of logs with roof thatching to shelter her fair skin from the harsh Florida sun while she was held prisoner.

This drawing depicts Gibbs and another pirate dumping the body of a woman over the side of the ship.

However, Gibbs’s newfound love interest did not sit well with his crew, who considered the girl an evil influence and potential danger. Gibbs killed one of his salty seamen after he tried to get her alone and bash her head in with a rock.

Gibbs considered the attack on his love interest an act of war, but the crew were convinced letting the girl live violated the sacred oath they held dear: no prisoners left alive.

Facing mutiny, Gibbs relented and killed the girl himself. He couldn’t bear the thought of shooting or stabbing her, so he had the cook prepare a deadly meal laced with poison to finish her off. She was buried in an unmarked grave on the island where she was held captive.

The U.S. schooner Porpoise, of the West Indies Squadron, was hot on the tail of Gibbs and his crew. They visited the island where Gibbs had held and killed the Dutch girl, and found evidence of her imprisonment in the pavilion and finally her unmarked grave. Because the island was uninhabited at the time, the Lieutenant on command marked it as Pavilion Key, which is what it is still called today.

Despite the evidence against them, Gibbs and his crew continued on their perilous rampage for many years. Finally they were attacked by the U.S. ship Enterprise and forced to retreat to an island after their ship was too badly damaged to go on. Gibbs reportedly left a pot of poison coffee over the fire hoping the Americans would drink it, but to no avail.

Gibbs and his pirate crew had no choice but to split up. Gibbs had planned on retiring, and so he took his share of the bounty and fled to New York City, briefly, then to Liverpool, where an Irish prostitute robbed him of everything he owned.

With no money and nowhere to go, Gibbs had no choice but to join a small crew and work as a mate aboard the vessel Vineyard, which was bound for the Americas. The cook had helped the captain load a chest of precious coin aboard the ship, and of course was sworn to secrecy. However, Gibbs was able to pry the information out of the cook then organized a mutiny.

On the night of November 23, 1822, Gibbs and his new followers brutally murdered the captain and first mate while the ship sailed off the coast of Cape Hatteras. A cabin boy who served as a passive, but not active accomplice, witnessed all the events.

Gibbs crowned himself the new Captain of Vineyard, but his new promotion was short-lived, as the ship sank and half the crew drowned off the coast of Long Island during a gale not long after the mutiny occurred.

Gibbs, the cabin boy and one other survived by taking one of the lifeboats to Pelican Island and buried loot they had managed to save from the sinking ship.

Gibbs and the cabin boy took a ferry to Great Barn Island and rented a horse and buggy and hit the road before Gibbs was recognized as a wanted man. However, their third companion refused to go on. He had secretly sent a message to the local magistrate admitting to the murderous mutiny that occurred aboard the Vineyard.

Gibbs and the cabin boy were soon apprehended. After the boy testified against Gibbs in a court of law, the jury found Gibbs and two other crew members (discovered elsewhere) guilty of murder in the first. They were sentenced to death and finally hanged for their crimes at high noon on April 22.

Gibbs's final words before he was hanged were, "No mercy did we show, for dead men tell no tales," 

Age 33 seems young to end one's life. However, Gibbs had been one of the most successful and ruthless American pirates since he was a young teenager. While his youth was lost when he entered into piracy, his bloody plight will forever live on, serving as the inspiration behind pirate tales and legends for generations to come.