In 1360, John II signed the Treaty of Brétigny, which gave England control of Aquitaine, Calais, and Ponthieu and a large ransom for John II’s release. A number of high-profile hostages were sent to England to guarantee the payment of the ransom, including Louis, the Duke of Anjou, one of John II’s sons. However, the Duke of Anjou escaped. As a result of this breach of the agreement, John II chivalrously agreed to return to England as a prisoner, despite the opposition of his council. John II was treated well and allowed to stay with other French prisoners at the Savoy Palace in London. There, he fell ill and died in 1364, leaving the throne to his eldest son, the Duke of Normandy, who became King Charles V.

With France and England at peace, many of the Free Companies were hired to fight in a civil war in the Spanish kingdom of Castile between King Peter “the Cruel” and his illegitimate brother, Henry of Trastámara. The Black Prince at first supported Peter the Cruel, but after finding that Peter was indeed very cruel, the Black Prince stopped backing him.

Peter the Cruel holed up at the castle of Montiel.