The Battle of Winchelsea

On August 29, 1350, at the Battle of Winchelsea, the English naval fleet under King Edward III defeated a Castilian fleet of 40 ships. An excerpt from the article:

"In 1350, King Edward III of England was at peace—with Scotland, after capturing King David II at the Battle of Neville’s Cross in 1346, and with France, after a decisive victory at the Battle of Crécy in the same year. For many years, however, trouble had been brewing with Castille—a Spanish kingdom whose navy had taken to raiding English ships in the Channel. A chance for restitution came when news reached Edward that a Spanish fleet had sailed to Flanders to trade wool. “We have for a long time spared these people,” he announced, “for which they have done us much harm; without amending their conduct; for on the contrary, they grow more arrogant; for which reason they must be chastised.” He resolved to intercept the fleet as it returned to Castille—a feasible operation in the narrow waters of the English Channel.

Edward assembled a fleet of 50 ships by the usual means of conscripting merchantmen and outfitting them for war, and issued a summons to his lords and knights. At least 17 lords and more than 400 knights responded, creating a top-heavy command structure on board ship; at the time, the title of “captain” was essentially a military one, and it was held by the lord or knight who commanded the troops on board. The fleet gathered off Winchelsea, then a significant harbor on the south coast and one of the Cinque Ports, which were obliged to maintain ships for the Crown in case of need. Edward’s warrior son, the Black Prince, and the 10-year-old John of Gaunt were among the troops, as was Robert of Namur, Edward’s favorite knight, who took charge of the Salle de Roi, which carried the King’s household.

Meanwhile, the Spanish fleet of 47 ships had loaded up with linen at Sluys, in Flanders, where the English had sunk most of the French fleet 10 years earlier. Don Carlos de la Cerda, the Spanish commander, had heard of Edward’s plans and armed his ships accordingly; as many cannons as he could find were lifted aboard, and the wooden “castles” atop the ships’ masts were stocked with stones and iron bars to drop on the English vessels. When they raised anchor, the ships, according to the Flemish chronicler Jean Froissart, were “so beautiful, it was a fine sight to see them under sail.”

Edward sailed in the Cog Thomas, commanded by Robert Passelow, and the fleet cruised between Dover and Calais. He enjoyed himself as he waited for the Spanish, encouraging Sir John Chandos, his tactician at the battle of Crécy, to sing with the royal minstrels. Eventually, late in the afternoon of August 29, the lookout caught sight of the Spanish. “I see two, three, four, and so many that, God help me, I cannot count them,” he cried. The minstrels were silenced and the king offered wine to his knights, who drank and put on their helmets. Always conscious of his image, Edward stood at the prow of the ship, dressed, according to Froissart, in a black velvet jacket and a beaver hat, “which became him very much.”

The Spanish had the wind behind them and could have declined battle (they had more to lose with valuable cargoes on board) but “their pride and presumption made them act otherwise.” The king shouted to Passelow, “Steer for that ship for I want to joust with her,” since he loved tournaments and had recently revived the Arthurian ideal of chivalry. Normally the master of the ship had the right to advise on such matters, but in this instance he remained silent:

The sailor did not want to disobey his orders because it was the King who desired it, even though the Spaniard came on at speed sailing on the wind. The King’s ship was strong and manoeuvrable, otherwise she would have split; for she and the great Spanish vessel struck with such force that it sounded like thunder and as they rebounded the castle of the King of England’s ship caught the [top]castle of the Spanish ship in such a way that the mast levered it from the mast on which it was fixed and it fell in the sea. All those in the castle were drowned and lost.

But the Spanish ship was not the only vessel damaged in the collision. The seams between the planks of the Cog Thomas opened and she began to take on water. The knights pumped and baled, but did not dare to tell the King, who looked at the ship alongside the one he had “jousted” with and called out, “Grapple my ship to that one; I must have her!” One of the knights exclaimed, “Let her go, you’ll get a better!” and soon another vessel drew near and the knights snared it with grappling hooks and chains:

The English royal knights made strenuous efforts to take the ship they had grappled with because their own… was in danger of foundering as she had taken in so much water. At last the King and his crew fought so well that the Spanish ship was taken and everyone on board her was thrown over the side. Then they told the King of his peril from the sinking ship and that he should go on board the prize vessel. The King took this advice and went on board the Spanish ship with all his men leaving the other empty.

The battle raged around the English as they drew close to the Spanish, who shot arrows and pelted them with iron bars. Night was falling and the English were anxious to reach a conclusion, but the Spanish were “people well used to the sea and with large well-equipped ships.” The Black Prince soon became embroiled in a fight of his own as his ship grappled a large Spanish vessel. His ship was holed in several places, perhaps by the iron bars, and was beginning to sink when the Duke of Lancaster came alongside in his own ship. The old crusader called out “Derby to the rescue!”—since he was also the Earl of Derby—and boarded the Spanish vessel. He was victorious, and again the captured enemy prisoners were thrown overboard."