At the beginning of the Hundred Years War, the bishop entrusted defence of the castle to Guichard d'Angle. Guichard became Seneschal of Saintonge and fought for the King of France during the battle of Poitiers in 1356. Following the French defeat, he was forced to cede the castle at Angles to the King of England and fight alongside his son, the Black Prince.
A legend was born out of these troubled times. The "Tranchée des Anglais" or English Trench is a naturally occurring fault in the cliff in which a set of steps was subsequently carved, linking the banks of the river Anglin to the summit of the promontory. According to legend, it was Guichard himself who carved out the steps, in a single night, in order to retake the castle with the help of a small band of Englishmen. It is these events that gave the "English Trench" its name.
On the 23rd of May 1372, the castle was retaken peacefully by Bertrand de Guesclin who, hailing from Berry, was set to recapture Poitou from the English.