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Raynald was held in prison until 1176. After his release for a large ransom, he did not return to Antioch, because his wife had meanwhile died. He married Stephanie of Milly, the wealthy heiress of Oultrejordain. Since Baldwin IV of Jerusalem also granted Hebron to him, Raynald was one of the wealthiest barons of the realm. He controlled the caravan routes between Egypt and Syria. Baldwin, who suffered from leprosy, made him regent in 1177. Raynald led the crusader army that defeated Saladin at the Battle of Montgisard. He was the only Christian leader to pursue an offensive policy against Saladin, making plundering raids against the caravans travelling near his domains. He built a fleet of five ships which plundered the coast of the Red Sea, threatening the route of the Muslim pilgrims towards Mecca in early 1183. Saladin pledged that he would never forgive Raynald.