A Pirate’s Life: 6 Swashbuckling Medieval Pirates

A Pirate’s Life: 6 Swashbuckling Medieval Pirates

Stephanie Schoppert - June 20, 2017

A Pirate’s Life: 6 Swashbuckling Medieval Pirates
Henry Paye’s ship. antiquestradegazette.com

Henry Paye of Poole (1364 – 1419)

Henry or Harry, Page or Arripaye was born around 1364 and grew up to be a privateer and smuggler. He was from Poole, Dorset and despite having a life as a notorious pirate he became a commander of the Cinque Ports fleet. He started his life on sea by leading naval raids along the coast of France and Spain. His attacks ranged from Normandy through the Bay of Biscay and Cape Finisterre. He was pivotal in helping to put down the Welsh revolts that were headed by Owain Glyndwr and defeating a French fleet that was dispatched in order to assist the rebels. He became a well-known and greatly feared pirate throughout the southern seas.

His life is remembered through stories of his exploits as a fearsome pirate sailing upon the Mary. His ship was licensed to carry pilgrims to Spain but instead, he used to ship to capture vessels and raid towns. He stole a treasured golden cross from the Finisterre church which was never recovered. He also burned down the walled city of Gijon. The reason for burning the town might have been personal as the Spanish city was the home of his known lover Countess Isabel. His actions against the Spanish sparked their anger and they sought brutal revenge against the hated pirate.

In 1405 a group of French and Spanish galleys made their way along the south coast when they reached Poole. They learned the town was the home of Arripaye the pirate and decided to destroy the town. Many were killed and the villagers were forced to flee, allowing the Spanish to burn the town to the ground. In 1407, Henry sought his revenge and led a fleet of 15 ships up and down the English Channel capturing French and Spanish cargo ships. Archives report 120 ships were captured all of which were loaded with valuable goods and massive quantities of wine. Henry brought all the ships to the people of Poole to compensate them for their suffering. Local tradition says that the town feasted for days on the proffered food and wine.

Few pirates have as many daring stories as Henry Poole. He was once captured by the French. He and his shipmates were being held on the deck of their ship by a small number of guards while the rest went below deck to search for treasure. However, Henry and his men broke free of their bindings and killed all the Frenchmen. He then took control of two French ships and sailed them up the Seine, using the French flag as a means to plunder several ships before making his way out to sea. He was eventually made Warden of the Cinque Ports and retired on a Royal pension. He died in 1419 and there is a memorial in Faversham Church in Kent where he was buried.

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