The example of Jean de Boniface made a strong impression on Jacques, and in 1446 he decided to take up the profession of knight-errant, traveling from court to court with his entourage of 80 to 100 men-at-arms searching for opportunities to gain fighting acclaim. Traveling to France, and then to Navarre and Castile, Jacques sought combat with whoever would fight. Unfortunately, both King Charles VII of France and King John II of Navarre denied him permission to fight, probably because they did not want to spend money on an expensive tournament. However, after riding through Spain and Portugal, he was given the chance to fight in Valladolid on 3 February 1447, when King John II of Castile allowed him to fight Diego de Guzman, the son of the Grandmaster of the Spanish Order of Calatrava. Combat began on foot, and Jacques was so successful in beating his rival that the mounted combat never took place. On his way back home to Hainault, Jacques stopped in Aragon but was refused permission to fight yet again.