Harry had a colourful life, He and his ship the Mary appear in the kings records as being licensed to carry pilgrims to Spain. The Spanish archives record him as stealing the gold cross from the church at Finisterre. He was notorious for having burnt the Spanish walled city of Gijon, home of his lover, the Countess Isabel.  Harry's activities in Spain drove the Spanish to seek revenge. In 1405 a squadron of Spanish and French galleys were making their way along the south coast. When they reached Poole they heard that it was home town to the dreaded Arripaye who was away with the English fleet. The galleys were crammed with heavily armed fighting men who attacked the town. The people of Poole fought valiantly and the fighting was fierce with many killed on both sides, including Harry's brother. Eventually the Poole people were forced to flee to the heath leaving the raiders to burn the town.

Two years later, in 1407, Harry decided it was "paye back" time. His ship and 14 others swept the English Channel capturing French and Spanish cargo vessels. The archives record that 120 ships were captured loaded with valuable goods including vast quantities of good French wine. To help to recompense the people of Poole for their sufferings Harry brought the captured ships back to Poole. According to local tradition the town feasted and drank the captured wine for many days.